Alcohols Phenols and Ethers

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11. ALCOHOLS PHENOLS AND ETHERS
#QID# 43636
(1.)
Product is
(a.)
(b.)
(c.)
(d.) Both (a) and (b)
ANSWER: c
#QID# 43659
(2.)
(a.)
(b.)
(c.)
(d.)
ANSWER: b
EXPLANATION: (b)
C − Br bond is weaker as compared to C − Cl bond
#QID# 43682
(3.) What amount of bromine will be required to convert 2 g of phenol into 2,
4, 6-tribromo phenol?
(a.) 4.00
(b.) 6.00
(c.) 10.22
(d.) 20.44
ANSWER: c
EXPLANATION: (c)
Molecular weight of phenol= 12 × 6 + 1 × 6 + 16 = 94

Molecular weight. Of Br2 = 3 × 160 = 480
∵ 94 g of phenol requires=480g of Br2
480
∴ 2 g phenol requires= × 2 = 10.22 g
94
#QID# 43513
NaNO2 /H2 SO4 H2 O NaOH
(4.) Phenol → 𝐵 → 𝐶 → 𝐷
Name of the above reaction is
(a.) Liebermann’s reaction
(b.) Phthalein fusion test
(c.) Reimer-Tiemann reaction
(d.) Schotten-Baumann reaction
ANSWER: a
EXPLANATION: (a)
This reaction is an example of coupling reaction
#QID# 43490
(5.) Which reagent can distinguish C2 H5 OH and ϕ OH?
(a.) SOCl2
(b.) CH3 COCl
(c.) (CH3 CO)2 O
(d.) CH3 COOH
ANSWER: a
#QID# 43559
(6.) The correct order of boiling point for primary (1°), secondary (2°) and
tertiary (3°)alcohols is
(a.) 1° > 2° > 3°
(b.) 3° > 2° > 1°

(c.) 2° > 1° > 3°
(d.) 2° > 3° > 1°
ANSWER: a
EXPLANATION: (a)
Alcohols with same molecular weight are expected to have almost same boiling
point however two more factors other than molecular weight are important, they
are namely H-boiling and surface area of molecule. Both these factors are least
in 3° alcohols and maximum in 1° alcohols. Hence, 3° alcohols have least boiling
point while 1°alcohols have maximum boliling point.
#QID# 43536
(7.)
Product obtained is
(a.)
(b.)
(c.)
(d.)
ANSWER: b
#QID# 43679
(8.) On treatment with a concentrated solution of zinc chloride in concentrated
HCl at room temperature, an alcohol immediately gives, an oily product.
The alcohol can be
(a.) C6 H5 CH2 OH
(b.) CH3 CHOHCH3
(c.) CH3
|
CH3 − C − OH
|
CH3
(d.) Any of these
ANSWER: c
EXPLANATION: (c)
In Lucas test, when alcohol is mixed with conc HCl and anhydrous ZnCl2 at room
temperature, if oily product is formed immediately, the alcohol can be tertiary
#QID# 43579
(9.) Phenol on treatment with diethyl sulphate in presence of NaOH gives
(a.) Phenetole
(b.) Anisole
(c.) Diphenyl ether
(d.) Diethyl ether
ANSWER: a
EXPLANATION: (a)
Diethyl sulphate in the presence of NaOH acts as alkylating agent, it causes

alkylation of phenol to give ethyl phenyl ether which is also called phenetole.
C6 H5 OH + NaOH → C6 H5 O− Na+ + H2 O
C6 H5 O− Na+ + (C2 H5 )2 SO4 → C6 H5 OC2 H5 ph + C2 H5 NaSO4
diethyl sulphate phenetole
#QID# 43493
(10.) The main product of the following reaction is
Conc.H2 SO4
C6 H5 CH2 CH(OH)CH(CH3 )2 → ?
(a.)
(b.)
(c.)
(d.)
ANSWER: a
#QID# 43639
(11.) When o-or p-phenol sulphonic acid is treated with bromine water, the
product formed is
(a.) 2, 4-dibromophenol
(b.) 2, 4, 6-tribromophenol
(c.) 3-bromophenol boric acid
(d.) 3, 5-dibromophenol
ANSWER: b
EXPLANATION: (b)
Like nitration, bromination of o-or p-phenolsulphonic acid occurs with

simultaneous replacement of SO3 H group by Br atom to ultimately give 2, 4, 6-
tribromophenol.
#QID# 43616
(12.) CH3 − CH2 − O − CH2 − CH3 reacts with hot and excess HI, then formed
product is
(a.) CH3 − CH2 − I and CH3 CH2 OH
(b.) CH3 − CH2 − OH
(c.) CH3 − CH2 − I
(d.) None of the above
ANSWER: c
EXPLANATION: (c)
Ether on reaction with excess of HI produce two molecules of alkyl halide.
Ethyl iodine
When equimolar quantities of ether and HI are present, then one molecule of alkyl
halide and one molecule of alcohol are formed.
#QID# 43662
(13.) Ethyl chloride reacts with sodium ethoxide to form a compound A. Which
of the following reactions also yields A?
(a.) C2 H5 Cl, KOH (alc. ), Δ
(b.) 2C2 H5 OH, conc. H2 SO4 , 140℃

(c.) C2 H5 Cl, Mg(dry ether)
(d.) C2 H2 , dil H2 SO4 , HgSO4
ANSWER: b
EXPLANATION: (b)
Ethyl chloride reacts with sodium ethoxide to form diethyl ether as
diethyl ether
Diethyl ether is also obtained by reaction of ethyl alcohol with conc. H2 SO4 at
140℃.
#QID# 43702
(14.)
This reaction is called
(a.) Reimer- Tiemann reaction
(b.) Lederer-Manasse reaction
(c.) Sandmeyer reaction
(d.) Kolbe’s reaction
ANSWER: b
EXPLANATION: (b)
Phenol condenses with aliphatic and aromatic aldehydes in the 𝑜- and 𝑝-positions,
the most important example being the condensation with formaldehyde. This is
known as Leaderer-Manasse reaction
#QID# 43510
(15.) In the reaction,
The products are
(a.)
(b.)
(c.)
(d.)
ANSWER: d
#QID# 43556
(16.) The most unlikely representation of resonance structures of 𝑝-
nitrophenoxide ion is
(a.)
(b.)
(c.)
(d.)
ANSWER: c
EXPLANATION: (c)
is not a resonating structure of 𝑝-nitrophenoxide

Since, N being an element of second period can’t contain more than 10 electrons
in its valence shell
#QID# 43599
(17.) Mild oxidation of glycerol with H2 O2 /FeSO4 gives
(a.) Glyceraldehyde
(b.) Dihydroxy acetone
(c.) Both(a) and (b)
ANSWER: c
EXPLANATION: (c)
With mild oxidising agent like bromine water or H2 O2 in the presence of FeSO4
(Fenton’s reagent), glycerol is oxidised to a mixture of glyceraldehyde and
dihydroxy acetone
#QID# 43725
(18.) C2 H5 OH and C2 H5 OH can be distinguished by
(a.) Br2 + H2 O
(b.) FeCI3
(c.) I2 + NaOH
(d.) Both (b) and (c)
ANSWER: d
EXPLANATION: (d)
C2 H5 OH and C6 H5 OH can be distinguished by neutral FeCl3 solution or I2

+NaOH solution. C2 H5 OH gives iodoform test with I2 + NaOH solution while
phenol does not give yellow ppt. of iodoform.
Δ
C2 H5 OH + 4I2 + 6NaOH → CHI3 + HCOONa + 5NaI + 5H2 O
iodoform
C6 H5 OH + I2 + NaOH → No reaction
C6 H5 OH reacts with neutral FeCl3 solution to give purple colour while C2 H5 OH
doesn’t give any colour with neutral FeCl3 solution.
#QID# 43533
(19.) Phenol can be distinguished from ethanol by the following reagents except
(a.) Sodium
(b.) NaOH/I2
(c.) Neutral FeCI3
(d.) Br2 /H2 O
ANSWER: a
EXPLANATION: (a)
Phenol cannot be distinguished from ethanol by sodium because both evolve

hydrogen with sodium.
2C6 H5 OH + 2Na → 2C6 H5 ONa + H2 ↑
2C2 H5 OH + 2Na → 2C2 H5 ONa + H2 ↑
#QID# 43619
(20.)
In the above reaction 𝐴 is
(a.)
(b.)
(c.) CH2 = CHOH
(d.) None of these
ANSWER: b
#QID# 43496
(21.) CH3
|
Acid
(CH3 )2 CHCHOH → 𝑋
–H2 O
The major product obtained in this reaction is
(a.) (CH3 )2 CHCH = CH2
(b.) (CH3 )2 C = CH − CH3
(c.) 1 : 1 mixture of (a) and (b)

ANSWER: b
EXPLANATION: (b)
Many a time unexpected products result during dehydration of alcohols.
#QID# 43642
(22.) Which alcohol cannot be oxidized by MnO2 ?
(a.) CH2 = CH − CH2 CH2 OH
(b.) CH3 − CH = CH − CH2 OH
(c.) ϕCH2 OH
(d.)
ANSWER: a
#QID# 43596
(23.) Lucas reagent is
(a.) Anhydrous AlCl3 with concentrated HCl

(b.) Anhydrous ZnCl2 and concentrated H2 SO4
(c.) Anhydrous ZnCl2 and concentrated HCl
(d.) Anhydrous CaCl2 and concentrated HCl
ANSWER: c
#QID# 43745
(24.) The correct order of ease of dehydration of following is
(a.) I > II > III
(b.) III > II > I
(c.) I > III > II
(d.) III > I > II
ANSWER: b
EXPLANATION: (b)
The correct order of stability of carbocation is as follows
#QID# 43699
(25.) What is the hybridisation of carbon and oxygen in electronic structure of
ether?
(a.) 𝑠𝑝3 and 𝑠𝑝2
(b.) 𝑠𝑝3 and 𝑠𝑝3
(c.) 𝑠𝑝 and 𝑠𝑝
(d.) 𝑠𝑝2 and 𝑠𝑝2
ANSWER: b
EXPLANATION: (b)
𝑠𝑝3 and 𝑠𝑝3 -hybridisations of carbon and oxygen in electronic structure of ether.
#QID# 43553
(26.) Which of the following alcohols cannot be oxidized by potassium
dichromate in the presence of sulphuric acid?
(a.) CH3 CH2 OH
(b.) C6 H5 OH
(c.) C6 H5 CHOHCH3
(d.) CH3
|
CH3 − C − OH
|
CH3
ANSWER: d
#QID# 43765
(27.) Acidity of phenol is due to
(a.) Hydrogen bonding
(b.) Phenolic group
(c.) Benzene ring
(d.) Resonance stabilisation of its anion
ANSWER: d
EXPLANATION: (d)
All the reaction proceed by stable ions. After the lose of H + ion, phenol forms
phenoxide ion. The phenoxide ion is resonance stabilized, thus makes the phenol
more acidic.
#QID# 43742
(28.) Methylphenyl ether can be obtained by reacting
(a.) Phenolate ions and methyl iodide
(b.) Methoxide ions and bromobenzene
(c.) Methanol and phenol

(d.) Bromobenzene and methyl bromide
ANSWER: a
EXPLANATION: (a)
Methyl phenyl ether is obtained by the reaction of phenolate ions and methyl
iodine.
C6 H5 O− + CH3 I → C6 H5 OCH3 + I −
Methyl phenyl ether
#QID# 43722
(29.) A diazonium chloride reacts with ϕOH to give an azodye. The reaction is
called
(a.) Diazotisation
(b.) Condensation
(c.) Coupling
(d.) Reduction
ANSWER: c
EXPLANATION: (c)
Phenol forms azo dye, with benzene diazonium chloride. This reaction is called
coupling reaction
#QID# 43573
(30.) Which of the following does not react with sodium metal?
(a.) (CH3 )2 O
(b.) CH3 CH2 OH
(c.) CH3 COOH
(d.) C6 H5 OH
ANSWER: a
EXPLANATION: (a)
Only acidic compounds such as acetic acid, phenol and alcohol react with sodium
metal. Ether is not acidic in nature, hence it does react with sodium metal.
2CH3 CH2 OH + 2Na → 2CH3 CH2 ONa + H2
Ethanol sodium ethoxide
2CH3 COOH + 2Na → 2CH3 COONa + H2
Acetic acid sodium acetate
2C6 H5 OH + 2Na → 2C6 H5 ONa + H2
Phenol sodium
phenoxide
CH3 − O − CH3 + Na → No reaction
#QID# 43516
(31.) The correct order of acid strength of the following compounds is
I Phenol
II p-cresol
III m-nitrophenol
IV p-nitrophenol
(a.) IIII > II > I > IV
(b.) IV > III > I > II
(c.) II > IV > I > III

(d.) I > II > IV > III
ANSWER: b
EXPLANATION: (b)
Phenols are acidic in nature due to resonance stabilisation of phenoxide ion.

Presence of electrons releasing groups such as – CH3 destabilises ion and
decreases the acidic acidic nature of phenols. On the other hand presence of
electron withdrawing group in the ring stabilise phenoxide ion and increases the
acidic nature of phenols. Further more meta-isomer is less acidic. Then para
because it is stabilised by inductive effect only. Thus, correct order is IV > III >
I > II
#QID# 43656
(32.) The alcohol that produces turbidity immediately with ZnCI2 /conc. HCI at
room temperature
(a.) 1-hydroxy butane
(b.) 2-hydroxy butane
(c.) 2-hydroxy-2-methyl propane
(d.) 1-hydroxy-2-methyl propane
ANSWER: c
EXPLANATION: (c)
Mixture of anhydrous ZnCl2 and conc. HCl is known as Lucas reagent. Lucas test
is used for the distinction between primary, secondary and tertiary alcohols.
The tertiary alcohol reacts immediately with Lucas reagent producing turbidity.
The secondary alcohol gives turbidity within 5-10 min and primary alcohol
doesn’t give turbidity at all at room temperature. In the given alternates, 2-
hydroxy-2-methyl propane is 3° alcohol, so it is more reactive.
#QID# 43719
(33.) Dehydration of the following in increasing order is
(a.) I < II < III < IV
(b.) II < III < IV < I
(c.) I < II < III < IV
(d.) I < IV < II < III
ANSWER: a
EXPLANATION: (a)
Greater the conjugation, greater the stability due to resonance and easier the
dehydration. Thus, the correct order of dehydration is
#QID# 43739
(34.) Which of the following statements is not correct?
(a.) All alcohols are miscible with water
(b.) Only lower alcohols are miscible with water

(c.) All alcohols are not poisonous
(d.) Methanol is not poisonous
ANSWER: a
#QID# 43762
1.𝑁𝑎𝑂𝐻
2.𝐶𝑂2 /1400 𝐶 𝐻2 𝑂/𝐻 + Ac2 O
(35.) Phenol → 𝐴→ 𝐵→ 𝐶
In this reaction, the end product 𝐶 is
(a.) Salicylaldehyde
(b.) Salicylic acid
(c.) Phenyl acetate
(d.) Aspirin
ANSWER: d
#QID# 43594
(36.) Cumene process is the most important commercial method for the
manufacture of phenol. Cumene is
(a.) 1-methyl ethyl benzene
(b.) Ethyl benzene
(c.) Vinyl benzene

(d.) Propyl benzene
ANSWER: a
EXPLANATION: (a)
Cumene is iospropyl benzene (1-methyl ethyl benzene). It on oxidation gives

phenol.
#QID# 43651
(37.) Correct order of dehydration of
I (b)
(c) (d)
(a.) 𝐴 > 𝐵 > 𝐶 > 𝐷
(b.) 𝐵 > 𝐶 > 𝐴 > 𝐷

(c.) 𝐷 > 𝐴 > 𝐶 > 𝐴
(d.) 𝐷 > 𝐴 > 𝐵 > 𝐶
ANSWER: b
#QID# 43697
(38.) Anisole is the product obtained from phenol by the reaction known as
(a.) Coupling
(b.) Etherification
(c.) Oxidation
(d.) Esterification
ANSWER: b
EXPLANATION: (b)
In presence of NaOH or KOH, phenol reacts with alkyl halide and gives phenolic
ether (C6 H5 O𝑅).
𝑅𝑋
C6 H5 OH + NaOH → C6 H5 O − Na → C6 H5 − O − R
−𝐻2 𝑂 −Na𝑋
Vapours of C6 H5 OH and CH3 OH, with red hot ThO2 (thoria) give anisole
(phenolic ether).
ThO2
C6 H5 OH + CH3 OH → C6 H5 OCH3 + H2 O
Δ
anisole
#QID# 43720
(39.) The major product during hydroboration-oxidation of 1-
methylcyclopentene is
(a.)
(b.)
(c.)
(d.)
ANSWER: d
EXPLANATION: (d)
During hydroboration-oxidation, addition of H2 O across the double bond occurs

anti to Markownikoff’s rule and since the stereochemistry of addition 𝑐𝑖𝑠,
therefore 𝑡𝑟𝑎𝑛𝑠-2-methylcyclopentanol is formed
#QID# 43740
(40.) When diethyl ether is heated with an excess of PCl5 , it yields
(a.) Ethyl chloride

(b.) Diethyl ether peroxide
(c.) Ethanoyl chloride
(d.) Perchlorodiethy ether
ANSWER: a
#QID# 43571
(41.) Which one of the following alcohol is used as an antifreeze reagent for
making explosives?
(a.) Glycerol
(b.) Glycol
(c.) Ethanol
(d.) Phenol
ANSWER: a
EXPLANATION: (a)
Glycerol is generally used as an antifreeze reagent for making explosives.
#QID# 43528
𝑃𝐶𝑙5 Na
(42.) 𝐵 ← C2 H5 OH → 𝐴
𝐴+𝐵 →𝐶
CO
𝐶 → 𝐷
BF3
In the above sequence 𝐷 is
(a.) CH3 COOC2 H5
(b.) CH3 COOCH3
(c.) C2 H5 COOC2 H5
(d.) (C2 H5 )2 O → BF3
ANSWER: c
#QID# 43568
(43.) Carbocation is not the intermediate in
(a.) Hydroboration-oxidation of an alkene
(b.) Oxymercuration-demercuration of an alkene
(c.) Reaction of HCl with CH3 CH2 OH
(d.) All of the above
ANSWER: d
EXPLANATION: (d)
No one of the given reactions involve of formation of carbocation intermediate
#QID# 43591
(44.) When phenol is treated with excess of bromine water, it gives
(a.) m-bromophenol
(b.) o-and p-bromophenols
(c.) 2, 4-dibromophenol
(d.) 2, 4, 6-tribromophenol
ANSWER: d
#QID# 43760
(45.) Which of the following reactions can be used for the preparation of tert.
butylmethyl ether?
(a.) CH3 Br + (CH3 )3 CO− Na+ →
(b.) (CH3 )3 CCl + CH3 O− Na+ →
(c.) (CH3 )3 OH + CH3 Cl →
(d.) (CH3 )3 CCl + CH3 OH →
ANSWER: a
#QID# 43654
(46.)
Product is
(a.)
(b.)
(c.)
(d.)
ANSWER: c
#QID# 43505
Cu
C2 H5 OH → 𝑋
300℃
(vapour)
The molecular formula of X is
(a.) C4 H6 O
(b.) C4 H10 O
(c.) C2 H4 O
(d.) C2 H6
ANSWER: c
EXPLANATION: (c)
Alcohols are oxidised by not copper to give aldehydes.

Cu
C2 H5 OH → CH3 CHO Or C2 H4 O
300 ℃
acetaldehyde
#QID# 43694
(48.) Phenolphthalein is formed by condensation of phthalic anhydride and
ϕ OH. Which structure shows colour in basic medium?
(a.)
(b.)
(c.)
(d.) All of the above
ANSWER: b
EXPLANATION: (b)
Structure of phenolphthalein in basic medium is as follows.
#QID# 43717
(49.) What is formed when glycerol reacts with excess of HI?
(a.)
(b.)
(c.)
(d.)
ANSWER: c
EXPLANATION: (c)
When glycerol reacts with HI, 𝑖𝑠𝑜-propyl iodide is obtained
#QID# 43631
(50.)
𝐴 and 𝐵 respectively are
(a.)
(b.)
(c.)
(d.)
ANSWER: d
#QID# 43674
(51.) The correct order of reactivity of hydrogen halides with ethyl alcohol is
(a.) HF > HCl > HBr > HI
(b.) HCl > HBr > HF > HI
(c.) HBr > HCl > HI >HF
(d.) HI > HBr > HCl > HF
ANSWER: d
EXPLANATION: (d)
Among hydrogen halides, as the size of halide ion increases, its reactivity towards
ethyl alcohol also increases. Thus, the order of reactivity of hydrogen halide is
HI > HBr > HCl > HF
#QID# 43657
(52.) The products of combustion of an aliphatic thiol (𝑅𝑆𝐻) at 298 K are
(a.) CO2 (g), H2 O(g) and SO2 (g)
(b.) CO2 (g), H2 O(𝑙) and SO2 (g)
(c.) CO2 (𝑙), H2 O(𝑙) and SO2 (g)
(d.) CO2 (g), H2 O(𝑙) and SO2 (𝑙)
ANSWER: b
EXPLANATION: (b)
Aliphatic thiol on combustion give carbon dioxide, water and sulphur dioxide
#QID# 43734
(53.) Arrange the following in order of decreasing acidic strength. 𝑝-nitrophenol
(I), 𝑝-cresol (II), 𝑚-cresol (III), phenol (IV)
(a.) I > II > III > IV
(b.) IV > III > II > I
(c.) I > III > II > IV
(d.) III > II > I > IV
ANSWER: a
#QID# 43757
(54.) Which of the following combinations can be used to synthesise ethanol?
(a.) CH3 MgI and CH3 COCH3
(b.) CH3 MgI and C2 H5 OH
(c.) CH3 MgI and CH3 COOC2 H5
(d.) CH3 MgI and HCHO
ANSWER: d
#QID# 43634
(55.) Phenol, when it first reacts with concentrated sulphuric acid and then with
concentrated nitric acid, gives
(a.) 2, 4, 6-trinitrobenzene
(b.) o-nitrophenol
(c.) p-nitrophenol
(d.) Nitrobenzene
ANSWER: b
EXPLANATION: (b)
First sulphonation is the means to block para position and to reduce the reactivity
of
phenolic ring against strong oxidising agent HNO3 . (The use of conc. HNO3 over
phenol cause the oxidation of ring mainly). The strong acidic medium in second
step cause desulphonation (ipso mechanism) also.
#QID# 43611
(56.) Phenol on heating with CCI4 and aqueous KOH gives salicylic acid. This
reaction is
(a.) Friedel-Craft reaction
(b.) Diels-Alder reaction
(d.) Wittig reaction
ANSWER: c
EXPLANATION: (c)
Phenol on heating with CCl4 and aqueous KOH gives salicylic acid. This reaction
is Reimer-Tiemann reaction.
#QID# 43588
(57.) Ethylene glycol gives oxalic acid on oxidation with
(a.) Acidified K 2 Cr2 O7
(b.) Acidified KMnO4
(c.) Alkaline KMnO4
(d.) Periodic acid
ANSWER: c
EXPLANATION: (c)
In presence of HNO3 or alkaline KMnO4
#QID# 43511
Oxidation NH3
CH3 OH→ A→ B; A and B are
(a.) HCHO, HCOONH4
(b.) HCOOH, HCOONH4
(c.) HCOOH, HCONH2
(d.) HCHO, HCONH2
ANSWER: b
EXPLANATION: (b)
Oxidation NH3
CH3 OH→ HCOOH→ HCOONH4
(A) (B)
#QID# 43508
(59.) Acetic anhydride reacts with diethyl ether in the presence of anhydrous
AlCl3 to give
(a.) CH3 CH2 COOH

(b.) CH3 CH2 COOCH2 CH3
(c.) CH3 COOCH3
(d.) CH3 COOC2 H5
ANSWER: d
EXPLANATION: (d)
AlCl3
C2 H5 OC2 H5 + (CH3 CO)2 O→ CH3 COOC2 H5
Ethyl ether acetic anhydride ethyl acetate
#QID# 43714
(60.) The – OH group of an alcohol or the – COOH group of a carboxylic acid
can be replaced by – CI using
(a.) Phosphorus pentachloride
(b.) Hypochlorus acid
(c.) Chlorine
(d.) Hydrochloric acid
ANSWER: a
EXPLANATION: (a)
The –OH group of alcohol or the –COOH group of a carboxylic acid is replaced
by –Cl using phosphorus pentachloride (𝑖. 𝑒. , PCl5 )
𝑅OH + PCl5 → 𝑅Cl + POCl3 + HCl
alcohol
𝑅COOH + PCl5 → 𝑅COCl + POCl3 + HCl
acid
#QID# 43677
(61.) The dehydration of 2-methyl butanol with conc. H2 SO4 gives
(a.) 2-methyl butane as major product
(b.) Pentene
(c.) 2-methyl but-2-ene as major product
(d.) 2-methyl pent-2-ene
ANSWER: a
EXPLANATION: (a)
The reaction follows Saytzeff rule which says that during dehydration reaction
hydrogen is taken preferably from carbon atom having lesser hydrogen atoms.
#QID# 43491
(62.) Maximum dehydration takes place in that of
(a.)
(b.)
(c.)
(d.)
ANSWER: b
#QID# 43614
(63.) An organic compound A containing C, H and O has a pleasant odour with
boiling point of 78℃. On boiling A with concentrated H2 SO4 , a colourless
gas is produced which decolourises bromine water and alkaline KMnO4 .
The organic liquid A is
(a.) C2 H5 Cl
(b.) C2 H5 COOCH3
(c.) C2 H5 OH
(d.) C2 H6
ANSWER: c
EXPLANATION: (c)
The organic liquid A is C2 H5 OH

1Ethyl alcohol is a colourless liquid with a characteristic pleasant smell, having
boiling point 78.1℃.
Conc.H2 SO4
C2 H5 OH→ CH2 = CH2
(which decolourises Br2 water and alk. KMnO4 )
#QID# 43637
(64.) At 530 K, glycerol reacts with oxalic acid to produce
(a.) Allyl alcohol
(b.) Formic acid
(c.) Glyceraldehydes
(d.) Formaldehyde
ANSWER: a
EXPLANATION: (a)
Oxalic acid on reaction with glycerol at 530K temperature furnish allyl alcohol.
ol
#QID# 43551
(65.) The product obtained by the reaction of HBr with phenol is
(a.)
(b.)
(c.)
(d.) There is no reaction
ANSWER: d
EXPLANATION: (d)
Phenol reacts with PCl5 to form chlorobenzene. Halogenation of phenol does not
take place with H𝑋
#QID# 43554
(66.) Sodium phenoxide reacts with CO2 at 400 K and 4.7 atm pressure to give
(a.) Catechol
(b.) Salicylaldehyde
(c.) Sodium salicylate
(d.) Benzoic acid

ANSWER: c
EXPLANATION: (c)
Sodium phenoxide reacts with CO2 at 400 K and 4 − 7 atm pressure to give
sodium salicylate. This is called Kolbe’s reaction
#QID# 43574
(67.) In which molecule, cleavage by HlO4 is not observed?
(a.)
(b.)
(c.)
(d.)
ANSWER: a
EXPLANATION: (a)
All those compounds which have groups are oxidised by periodic

acid (HIO4 ). Thus is not oxidised.
#QID# 43494
(68.) In the following sequence of reactions,
𝑀𝑔
P+I2 𝐸𝑡ℎ𝑒𝑟 HCHO H2 O
CH3 CH2 OH→ 𝐴→ 𝐵→ 𝐶→ 𝐷
The compound ‘D ’ is
(a.) Butanal
(b.) n-butyl alcohol
(c.) n-propyl alcohol
(d.) Propanal
ANSWER: c
#QID# 43517
(69.) Propan-1-ol can be prepared from propane by
(a.) H2 O/H2 SO4
(b.) Hg(OAc)2 H2 O followed by NaBH4

(c.) B2 H6 followed by H2 O2
(d.) CH3 CO2 H/H2 SO4
ANSWER: c
EXPLANATION: (c)
Alkenes undergo addition reaction with diborane. The addition compounds on

hydrolysis with H2 O2 /OH− yield alcohols
B2 H6
CH3 − CH = CH2 → CH3 − CH2 − CH2 OH
H2 O2
#QID# 43663
(70.) In Lucas test an alcohol reacts immediately and gives insoluble chloride.
The alcohol is
(a.) CH3 OH
(b.) CH3 CH2 OH
(c.) (CH3 )2 CHOH
(d.) (CH3 )3 COH
ANSWER: d
EXPLANATION: (d)
A mixture of conc. HCl+ anhy ZnCl2 is called Lucas reagent. In Lucas test tertiary
alcohols immediately give turbidity while secondary alcohols give turbidity after
5 min. Primary alcohols give no reaction with Lucas reagent at room temperature.
Conc.HCI+anhy ZnCI2
CH3 OH/CH3 CH2 OH → No reaction
Primary alcohol
and hence, no white cloudiness on turbidity at room temperature.
Conc.HCI+anhy ZnCI2
(CH3 )2 CHOH→
Secondary alcohol
White cloudiness or turbidity appears within about 5 min.
Conc.HCl+anhy ZnCl2
(CH3 )3 COH → White cloudiness
Tertiary alcohol
Or turbidity appears immediately.
#QID# 43640
(71.) Phenol on reaction with CHCl3 and NaOH give benzaldehyde. Intermediate
of this reaction is
(a.) Carbocation
(b.) Carbanion
(c.) Radical
(d.) Carbene
ANSWER: d
EXPLANATION: (d)
Reimer-Tiemann reaction this involves the treatment of phenol with chloroform

in aqueous sodium hydroxide solution followed by acid hydrolysis.
Salicyladehyde is formed.
In the above reaction, chloroform first reacts with sodium hydroxide to produce
dichloro carbene which is the intermediate in this reaction.
#QID# 43540
(72.) Anisole can be prepared by the action of methyl iodide on sodium phenate.
The reaction is called
(a.) Wurtz’s reaction
(b.) Williamson’s reaction
(c.) Fittig’s reaction
(d.) Etard’s reaction
ANSWER: b
EXPLANATION: (b)
The reaction of alkyl halide with sodium alkoxide to give ether (alkoxy alkane)
is known as Williamson’s synthesis. In this reaction an ether (anisole) is prepared
by the action of alkyl halide (methyl iodide) on sodium alkoxide (sodium
phenate), so it is an example of Williamson’s synthesis.
#QID# 43686
(73.) Tert-butyl methyl ether on heating with anhydrous HI in ether gives
(a.) CH3 OH + (CH3 )3 CI
(b.) CH3 I + (CH3 )3 COH
(c.) CH3 I + (CH3 )3 Cl
ANSWER: b
EXPLANATION: (b)
Here, ether is the solvent. Being less polar, it favours SN 2 reaction and the
nucleophile I − attacks the 10 carbon of CH3 .
#QID# 43763
(74.) From amongst the following alcohols the one that would react fastest with
conc. HCI and anhydrous 𝑍𝑛𝐶𝐼2 is
(a.) 2-butanol
(b.) 2-methyl propan-2-ol
(c.) 2-methylpropanol
(d.) 1 butanol
ANSWER: b
EXPLANATION: (b)
The reaction of alcohol with conc. HCl and anhydrous ZnCl2 following SN 1
pathway, so greater the stability of carbocation formed, faster is the reaction.
2-methyl propan-2-ol gives 3° carbocation.
Hence, it reacts rapidly with conc. HCl and anhydrous ZnCl2 (Lucas reagent).
#QID# 43620
(75.) An ether is more volatile than an alcohol having the same molecular
formula. This is due to
(a.) Dipolar character of ethers
(b.) Alcohols having resonance structures
(c.) Intermolecular hydrogen bonding in ethers
(d.) Intermolecular hydrogen bonding in alcohols
ANSWER: d
EXPLANATION: (d)
Alcohol has polar H which makes intermolecular H-bonding possible. Ether is

non-polar hence no H-bonding. Lack of H-bonding in ether makes it more volatile
than alcohol.
#QID# 43706
(76.)
The product 𝐴 is
(a.)
(b.)
(c.)
(d.)
ANSWER: d
EXPLANATION: (d)
The pinacol-pinacolone rearrangement involves dehydration of diols through the

formation of carbocation intermediate which rearranges to more stable
compound.
#QID# 43537
(77.) Dunstan’ s test is used for identification of
(a.) Acetone
(b.) Ethanol
(c.) Glycerol
(d.) Glycol
ANSWER: c
EXPLANATION: (c)
Dunstan’s test is used for identification of glycerol
#QID# 43514
(78.) 𝑅CH2 CH2 OH can be converted to 𝑅CH2 CH2 COOH by the following
sequence of steps
(a.) PBr3 , KCN, H3 O+
(b.) PBr3 , KCN, H2 /P +
(c.) KCN, H3 O+
(d.) HCN, PBr3 , H3 O+

ANSWER: a
#QID# 43560
CH3
|
Conc.H2 SO4
CH3 − C − CH2 → A the product 𝐴 is
| |
OH OH
(a.) CH3
|
CH3 − C = CH2
(b.) H H
| |
CH3 − C = C − CH3
(c.) CH3
|
CH3 − CH2 − C = O
(d.) CH3
|
CH3 − CH − CHO
ANSWER: d
#QID# 43643
(80.) Pinacol is
(a.) 3-methylbutan-2-ol
(b.) 2, 3-dimethyl-2, 3-butanediol
(c.) 2, 3-dimethyl-2-propanone
ANSWER: b
EXPLANATION: (b)
2, 3-dimethyl butane-2, 3-diol is known as pinacol
#QID# 43497
(81.)
The product is
(a.)
(b.)
(c.)
(d.)
ANSWER: a
EXPLANATION: (a)
Catechol is most acidic out of all dihydric phenols.
The reaction is Williamson’s synthesis type reaction.
#QID# 43580
(82.) CH3 CH3
| |
Conc.H2 SO4
In the reaction Ph − C − C − Ph → 𝐴 The product 𝐴 is
| |
OH OH
(a.) CH3 CH3

| |
Ph − C = C − Ph
(b.)
(c.) CH3 O
| ||
Ph − C − C − CH3
|
Ph
(d.) CH3 O
| ||
Ph − C − C − Ph
|
CH3
ANSWER: c
#QID# 43623
(83.) By which the following reactions can 𝑡𝑟𝑎𝑛𝑠-cyclopentane-1, 2-diol be
obtained?
(a.)
(b.)
(c.)
(d.) None of these

ANSWER: c
#QID# 43749
(i)CH3 MgCl
(84.) → 𝑋
(ii)H2 O
The product obtained in this reaction is
(a.) CH3 CH2 OH
(b.) (CH3 )2 CHOH
(c.) CH3 CH2 CH2 OH
(d.) HO − CH2 − CH2 − CH2 − CH2 − OH
ANSWER: c
#QID# 43703
(85.) A fruity smell is obtained by the reaction of ethanol with
(a.) CH3 COCH3
(b.) PCI5
(c.) CH3 COOH
(d.) CH3 CHO
ANSWER: c
EXPLANATION: (c)
Alcohol + Acid ⇌ Ester(fruity smelling)

ROH RCOOH RCOOR
Alcohol (C2 H5 OH) when react with acid they produce ester and esters have fruity
smell.
C2 H5 OH + CH3 COOH → C2 H5 COOCH3 + H2 O
ethyl alcohol acetic acid fruity smell of ester
#QID# 43557
(86.) Hydroboration oxidation of 4-methyl octene would give
(a.) 4-methyl octanol
(b.) 2-methyl decane
(c.) 4-methyl heptanol
(d.) 4-methyl-2-actanone
ANSWER: a
EXPLANATION: (a)
Terminal alkenes react rapidly with diborane to form primary trialkyl boranes
which on oxidation gives primary alcohols.
(In general hydroboration oxidation involve
the addition of water according to anti-Markownikoff’s rule).
#QID# 43603
(87.) 2-methoxy butane is obtained by reacting diazomethane with
(a.) 2-butanol
(b.) 1-butanol
(c.) 2-butanone
(d.) Butanal
ANSWER: a
#QID# 43600
(88.) Primary, secondary and tertiary alcohols can be distinguished by
performing
(a.) Beilstein’s test
(b.) Victor Meyer’s test
(c.) Fehling’s solution test

(d.) Hofmann’s test
ANSWER: b
EXPLANATION: (b)
In Victors Meyer’s test, 1° −alcohol gives red colour, 2°-alcohol gives blue
colour while 3°-alcohol gives no colour.
#QID# 43577
(89.) In the Lucas test of alcohols, appearance of cloudiness is due to the
formation of
(a.) Aldehydes
(b.) Ketones
(c.) Acid chlorides
(d.) Alkyl chlorides
ANSWER: d
EXPLANATION: (d)
The Lucas test cloudiness (turbidity) appears due to the formation of alkyl
chloride
#QID# 43726
(90.) Two aromatic compounds having foemula C7 H8 O which are easily
identifiable by FeCI3 solution test (violet colouration) are
(a.) o-cresol and benzyl alcohol
(b.) m-cresol and p-cresol
(c.) o-cresol and p-cresol
(d.) Methyl phenyl ether and benzyl alcohol
ANSWER: a
EXPLANATION: (a)
o-cresol contains phenolic group, thus it gives violet colouration with FeCl3
where as benzyl alcohol donot contains phenolic group, hence no colouration
with FeCl3 . Hence, identifiable.
#QID# 43534
(91.) The reduction,
Can be achieved by using
(a.) NaBH4
(b.) LiAlH4
(c.) CuO ∙ CuCN2 O4
(d.) None of these
ANSWER: a
#QID# 43660
(92.) Phenol→ 𝐵→ 𝐶→ 𝐷
Name of the reaction is
(a.) Liebermann’s reaction
(b.) Phthalein fusion test
(d.) Schotten-Baumann reaction
ANSWER: a
EXPLANATION: (a)

Phenol→ 𝐵→ 𝐶→ 𝐷
This is Liebermann’s nitroso reaction of phenol. When phenol is warmed with
sodium nitrite and 1 cc. conc.H2 SO4 , blue colour is obtained which on adding
water, becomes red. This again turns to blue on adding NaOH. Deep blue colour
is due to the formation of sodium salt of indophenol.
#QID# 43683
(93.) Alcoholic beverages contain
(a.) Isopropyl alcohol
(b.) n-propyl alcohol

(c.) Ethyl alcohol
(d.) Methyl alcohol
ANSWER: c
#QID# 43520
𝑋
(94.) C6 H5 − CH = CHCHO→ C6 H5 CH = CHCH2 OH
In the above sequence X can be
(a.) H2 /Ni
(b.) NaBH4
(c.) K 2 Cr2 O7 /H +
(d.) Both (a) and (b)
ANSWER: b
EXPLANATION: (b)
NaBH4 and LiAlH4 attacks only carbonyl group and reduce it into alcohol group.
They do not attack on double bond.
NaBH4
C6 H5 − CH = CHCHO → C6 H5 − CH = CH. CH2 OH
cinnamic aldehyde cinnamic alcohol
#QID# 43746
(95.) When phenol reacts with phthalic anhydride in presence of 𝐻2 𝑆𝑂4 and
heated and hot reaction mixture is poured in NaOH solution, then product
formed is
(a.) Alizarin
(b.) Methyl orange
(c.) Fluorescein
(d.) Phenolphthalein
ANSWER: d
EXPLANATION: (d)
When phenol reacts with phthalic anhydride in presence of conc. H2 SO4 and
heated, then mixture is poured in NaOH solution the product formed is
phenolphthalein.
#QID# 43597
(96.) Reaction of tertiary butyl alcohol with hot Cu at 350℃ produces
(a.) Butanol
(b.) Butanal
(c.) 2-butene
(d.) Methylpropene
ANSWER: d
#QID# 43700
(97.) Which one of the following compounds will not react with CH3 MgBr?
(a.) Ethyl acetate
(b.) Acetone
(c.) Dimethyl ether
(d.) Ethanol
ANSWER: c
EXPLANATION: (c)
Grignard reagent (RMgX) reacts with only those compounds which contains
acidic hydrogen or which contains carbonyl group.
Dimethyl ether (CH3 OCH3 ) due to absence of both acidic hydrogen and carbonyl
group does not react with Grignard reagent.
#QID# 43743
(98.) Which is not the intermediate stage of following conversion?
Dil.H2 SO4
(CH3 )2 − C − C − (CH3 )2 → CH3 COC(CH3 )3
Δ
| |
OH OH
(a.)
(b.)
(c.)
(d.)
ANSWER: a
EXPLANATION: (a)
Pinacol (CH3 )2 − C(OH)C(OH)(CH3 )2 with dil H2 SO4 or HCl undergoes

dehydration and rearranges to form ketones (pinacolon)
#QID# 43617
(99.) Cyclohexanol on reaction with 𝑃𝐵𝑟3 in presence of pyridine gives
(a.) Bromocyclohexane
(b.) Bromocyclohexane
(c.) 1-bromocyclohexanol
(d.) None of these
ANSWER: a
EXPLANATION: (a)
Cyclohexanol on reaction with PBr3 in presence of pyridine gives

bromocyclohexane.
#QID# 43680
(100.) Correct acidic order of the following compounds is
(a.) I > II > III
(b.) III > I > II
(c.) II > III > I
(d.) I > III > II
ANSWER: b
EXPLANATION: (b)
Presence of electron withdrawing group such as NO2 , CHO etc, on benzene

nucleus, makes phenol more acidic by stabilising phenoxide ion while presence
of electron releasing groups such as – CH3 − C2 H5 destabilises the phenoxide ion,
thus makes the phenol less acidic. Hence, the order of acidity of given compound
is
#QID# 43723
HlO4
(101.) (𝐴 )→ cyclohexanone + HCHO. What is (𝐴)?
(a.)
(b.)
(c.)
(d.)
ANSWER: d
#QID# 43755
(102.) To prepare an ether by Williamson’s synthesis, the reactants needed are
(a.) Ethyl alcohol and tert butyl alcohol
(b.) Sodium ethoxide and tert butyl bromide

(c.) Sodium tertiary butoxide and ethyl bromide
(d.) Sodium ethoxide and sodium tert butoxide
ANSWER: c
EXPLANATION: (c)
1° alkyl halides on treatment with an alkoxide ion tend to undergo substitution to

form ethers. So sodium tert butoxide and ethyl bromide reagent is used
#QID# 43732
K2 Cr2 O7
H2 SO4 Oxidation
acetone → acetic acid→ 𝐴, 𝐴 is
(a.) 1-propanol
(b.) 2-butanol
(c.) 2-propanol
(d.) Ethanol
ANSWER: c
EXPLANATION: (c)
K2 Cr2 O7
CH3 CHOH → CH3 CH3 COCH3 → CH3 COOH
H2 SO4 oxidation
2-propanol acetone acetic acid
#QID# 43586
(104.) On reacting with neutral ferric chloride, phenol gives
(a.) Red colour
(b.) Blue colour
(c.) Violet colour
(d.) Green colour
ANSWER: c
EXPLANATION: (c)
Phenol reacts with neutral FeCl3 solution to give violet colour complex which is
soluble in water.
6C6 H5 OH + FeCl3 → [Fe(OC6 H5 )6 ]3− + 3H + + 3HCl
violet colour complex
#QID# 43609
(105.) During dehydration of alcohols to alkenes by heating with concentrated
𝐻2 𝑆𝑂4 the initiation step is
(a.) Protonation of alcohol molecule
(b.) Formation of carbocation
(c.) Elimination of water
(d.) Formation of an ester
ANSWER: a
EXPLANATION: (a)
Protonation of –OH is first step. Conversion of poor leaving group (-OH) into
good
+
leaving group(−OH ).
2
#QID# 43709
(106.) Denatured alcohol is
(a.) Ethanol + methanol
(b.) Rectified spirit + methanol + naphtha
(c.) Undistilled ethanol
(d.) Rectified spirit
ANSWER: a
#QID# 43563
(107.) The reaction,
Is called
(a.) Laderer Mannasse reaction
(b.) Claisen condensation
(c.) Benzoin condensation
(d.) Etard reaction
ANSWER: a
EXPLANATION: (a)
This reaction is called Laderer Mannasse reaction.
#QID# 43506
(108.) Alcohols cannot be prepared from
(a.) C2 H5 Br + aq. KOH →

LiAlH4
(b.) (CH3 )2 C = O →
(c.) O
||
Na/EtOH
CH3 − C − OCH3 →
H2 O
(d.) CH3 CH2 Cl →
ANSWER: d
EXPLANATION: (d)
Alkyl halides are hydrolysed to corresponding alcohols by moist silver oxide

(AgOH) or by boiling with aqueous alkali solution
Heat
𝑅𝑋 + AgOH→ 𝑅OH + Ag𝑋
#QID# 43583
(109.) Which of the following reagents may be used to distinguish between
phenol and benzoic acid?
(a.) Aqueous NaOH
(b.) Tollen’s reagent
(c.) Molisch reagent
(d.) Neutral FeCl3
ANSWER: d
EXPLANATION: (d)
Reagent Phenol Benzoic acid Conclusion
A Aqueous NaOH Salt formation Salt formation No specific colour
change
B Neutural FeCl3 Violet colour Buff-coloured
precipitate Thus, FeCl3 can be used to make distinction
#QID# 43632
(110.) An unknown compound ‘D ’ first oxidised to aldehyde and then acetic acid
by a dilute solution of K 2 Cr2 O7 and H2 SO4 . The compound ‘D ’ is
(a.) CH3 OH
(b.) C2 H5 OH
(c.) CH3 CH2 COOH
(d.) CH3 CH2 CHO
ANSWER: b
EXPLANATION: (b)
Oxidation K2 Cr2 O7
𝐷→ aldehyde → CH3 COOH
H2 SO4
acetic acid
1° alcohol on oxidation gives aldehyde having same number of carbon and
aldehyde on oxidation gives acid having same number of carbon atoms.
It means, D will be alcohol having two carbon atoms that is C2 H5 OH(ethyl
alcohol) and the alcohol on oxidation will give CH3 CHO (acetaldehyde)
[O] [O]
C2 H5 OH → CH3 CHO → CH3 COOH
(D)
#QID# 43729
(111.) Which of the following compound would not evolve CO2 when treated with
NaHCO3 solution?
(a.) Salicylic acid
(b.) Phenol
(c.) Benzoic acid
(d.) 4-nitrobenzoic acid
ANSWER: b
EXPLANATION: (b)
Phenol doesn’t decompose sodium carbonate or sodium bicarbonate, i.e., CO2 is

not evolved because phenol is a weaker acid than carbonic acid.
#QID# 43689
(112.) The correct order of decreasing acidity of nitrophenols will be
(a.) m-nitrophenol > p-nitrophenol > o-nitrophenol
(b.) o-nitrophenol > m-nitrophenol > p-nitrophenol
(c.) p-nitrophenol > m-nitrophenol > o-nitrophenol
(d.) p-nitrophenol > o-nitrophenol > m-nitrophenol
ANSWER: d
EXPLANATION: (d)
Due to –I and –R influence, NO2 in ortho-position should have raised the acidity
to the maximum extent. But it is due to intramolecular H-bonding, ortho-
nitrophenol is less acidic than para-nitrophenol.
#QID# 43752
(113.) Acid catalysed hydration of alkenes except ethene leads to the formation
of
(a.) Mixture of secondary and tertiary alcohols
(b.) Mixture of primary and secondary alcohols
(c.) Secondary or tertiary alcohol
(d.) Primary alcohol
ANSWER: c
EXPLANATION: (c)
Thus, best alternate is (c)
#QID# 43666
(114.) Consider the following reactions,
Anhydrous AlCl3 anhydrous ZnCl2 /HCl
𝑋 + HCl → C2 H5 Cl ← 𝑌
(addition) (substitution)
Y can be converted to X on heating with… at …. temperature.
(a.) Al2 O3 , 350℃
(b.) Cu, 300℃
(c.) Ca(OH)2 + CaOCl2 , 60℃
(d.) NaOH/I2 , 60℃
ANSWER: a
#QID# 43500
(115.) The enzymes which are used to convert starch into ethyl alcohol are
(a.) Maltase, diastase
(b.) Diastase, maltase, zymase
(c.) Invertase, zymase
(d.) Invertase, diastase, maltase
ANSWER: b
#QID# 43546
(116.) Which among the following compounds will give a secondary alcohol on
reacting with Grignard reagent followed by acid hydrolysis?
I. HCHO
II. C2 H5 CHO
III. CH3 COCH3
IV. HCOOC2 H5
Select the correct answer using the codes given below.
(a.) II only
(b.) III only
(c.) I and IV
(d.) II and IV
ANSWER: d
#QID# 43692
(117.) The final product obtained in the reaction,
(a.)
(b.)
(c.)
ANSWER: a
#QID# 43646
(118.) The structure of the compound that gives a tribromo derivative on
treatment with bromine water is
(a.)
(b.)
(c.)
(d.)
ANSWER: a
EXPLANATION: (a)
m-cresol due to phenoxide ion in H2 O solvent, gives tribromoderivative at all

ortho and para positions.
#QID# 43649
(119.) Which is not correct?
(a.) Phenol is more acidic than acetic acid.)
(b.) Ethanol is less acidic than phenol.

(c.) Ethanol has higher boiling point than ethane.)
(d.) Ethane is non-linear molecule.
ANSWER: a
EXPLANATION: (a)
Phenol are less acidic than carboxylic acid, because carboxylate ion is relatively
more stable as compared to phenoxide ion.
#QID# 43569
(120.) Grignard reagent reacts with HCHO to produce
(a.) Secondary alcohol
(b.) Anhydride
(c.) Acid
(d.) Primary alcohol
ANSWER: d
EXPLANATION: (d)
Aldehydes and ketones on reaction with 𝑅𝑀𝑔𝑋 followed by subsequent
hydrolysis in acidic gives alcohol. e.g.;
|
R
2°alcohol
#QID# 43669
Br
(121.) → C2 H6 𝐴𝐵𝐶
H2 O
In the above sequence, C is
(a.) o-bromophenol
(b.) p-bromophenol
(c.) m-bromophenol
ANSWER: d
#QID# 43626
(122.) Which of the following reaction is/are feasible?
(a.)
(b.)
(c.) Both(a) and (b)
ANSWER: a
EXPLANATION: (a)
The reactivity of primary halides is in the order, CH3 > CH3 CH2 > CH3 CH2 CH2
and the tendency of alkyl halides to undergo elimination is 3° > 2° > 1°. Hence,
for better yield, the alkyl halide should be primary and alkoxide should be
secondary or tertiary.
#QID# 43526
(123.) Which of the following compounds is most acidic?
(a.) CH4
(b.) C2 H6
(c.) CH ≡ CH
(d.) C2 H5 OH
ANSWER: d
EXPLANATION: (d)
Proton donors are acids. Among given choices C2 H5 OH can give proton (H + )
most easily.
∴ C2 H5 OH is most acidic among C2 H6 , CH4 ,
CH ≡ CH and C2 H5 OH
#QID# 43589
(124.) Picric acid is a stronger acid than acetic acid and benzoic acid. It contains
(a.) −SO3 H group
(b.) Two – COOH groups
(c.) Phenolic group
ANSWER: d
EXPLANATION: (d)
Picric acid is 2, 4, 6-trinitrophenol. It is due to presence of three –I showing –

NO2 groups, is more acidic than acetic acid and benzoic acid.
#QID# 43566
(125.) Among the alkenes which one produces tertiary butyl alcohol on acid
hydration?
(a.) CH3 CH2 CH = CH2
(b.) CH3 CH = CH − CH3
(c.) (CH3 )2 C = CH2
(d.) CH3 − CH = CH2
ANSWER: c
#QID# 43543
Reaction
(126.) Chlorobenzene → Phonel
𝑌
Salicyladehyde X and Y reactions are respectively……….
(a.) Fires rearrangement and Kolbe-Schmidt
(b.) Cumene and Reimer-Tiemann
(c.) Dow and Reimer-Tiemann

(d.) Dow and Friedel-Craft
ANSWER: c
EXPLANATION: (c)
Dow′ s process Reimer−Tiemann

Chloro benzene → Phenol → Salicylaldehyde
reaction
#QID# 43712
(127.) Identify the product/s in the following reaction.
𝐵𝐻3 H2 O2 /OH−
3CH3 CH = CH2 → 𝑋 → Products +H3 BO3
(a.) CH3 CH2 CH2 OH
(b.) CH3 CHOHCH3
(c.) CH3 CH2 CHO
(d.) CH3 CH2 OH + CH3 OH
ANSWER: a
#QID# 43735
(128.) In the reaction for dinitration
(a.)
(b.)
(c.)
(d.)
ANSWER: a
#QID# 43606
(129.) Argol, a brown crust, formed during the fermentation of grape juice
contains
(a.) CO2
(b.) Fused oil
(c.) Potassium hydrogen tartarate

(d.) lye
ANSWER: c
EXPLANATION: (c)
During germentation of grape juice, a brown crust is formed at the top which is
called argol. This contains potassium hydrogen tartrate and is used for preparation
of tartaric acid and Rochelle salt.
#QID# 43503
(130.) The products obtained when anisole is heated in a sealed tube with HI are
(a.)
(b.)
(c.)
(d.) CH3 OH + CH3 I
ANSWER: a
EXPLANATION: (a)
When an alkyl aryl ether is heated with HI, halogen goes with alkyl group.
Therefore, heating anisole (methyl phenyl ether) with HI phenol and methyl
iodide are obtained.
#QID# 43652
(131.) The compound which gives turbidity immediately with Lucas reagent at
room temperature is
(a.) Butan-1-ol
(b.) Butan-2-ol
(c.) 2-methyl propan-2-ol
(d.) 2-methyl propan-1-ol
ANSWER: c
EXPLANATION: (c)
In case of 3° alcohols (tertiary alcohols) turbidity appears immediately at room

temperature.
#QID# 43672
(132.) When phenolic ether is heated with HI, it yields
(a.) Alkyl halide + aryl halide + water

(b.)
(c.) Alcohol +aryl halide
ANSWER: b
EXPLANATION: (b)
When phenolic ether is heated with HI, it gives alkyl halide and phenol
#QID# 43523
(133.) Consider the following reaction,
product 𝑋 is
(a.) Picric acid
(b.) Styphnic acid
(c.) Salicylic acid
(d.) Benzoic acid
ANSWER: b
#QID# 43629
𝑃/𝐼2 𝐴𝑔𝑁𝑂2 𝐻𝑁𝑂2 NaOH
(134.) 𝐼𝑠𝑜-butyl alcohol → → → → 𝐴
True statement about 𝐴 is
(a.) Blue coloured solution
(b.) Blue precipitate
(c.) Red precipitate
(d.) Red coloured solution
ANSWER: a
EXPLANATION: (a)
𝐼𝑠𝑜-butyl alcohol is secondary alcohol
#QID# 43715
(135.) If the boiling point of ethanol (molecular weight=46) is 78℃, what is the
boiling point of diethyl ether?
(molecular weight=74)
(a.) 100℃
(b.) 78℃
(c.) 86℃
(d.) 34℃
ANSWER: d
EXPLANATION: (d)
Molecular weight of diethyl ether is more than ethanol. Therefore, it should have
higher boiling point than ethanol. But it is not so. It is due to intermolecular
hydrogen bonding. Ethyl alcohol has intermolecular hydrogen bonding but
diethyl ether has no hydrogen bonding. The compounds shows intermolecular
hydrogen bonding has higher m.p. and b.p. than compounds having no hydrogen
bonding. Therefore, the boiling point of diethyl ether will be less than ethanol
(78℃).
#QID# 43701
(136.) The product obtained by heating diethyl ether with HI is
(a.) C2 H5 I
(b.) C2 H5 OH
(c.) C2 H5 OH + C2 H5 I
(d.) C2 H5 − C2 H5
ANSWER: c
EXPLANATION: (c)
C2 H5 OC2 H5 + HI → C2 H5 OH + C2 H5 I
#QID# 43655
(137.) The final product (IV) in the sequence of reactions
is
(a.) CH3 − CHOCH2 CH2 OH

|
CH3
(b.) CH3 − CHCH2 CH2 Br

|
CH3
(c.) CH3 − CH − CH2 CH2 OH

|
CH3
(d.) CH3 − CHOCH2 CH3

|
CH3
ANSWER: c
#QID# 43598
Jones
(138.) CH3 CH = CH − CH − CH3 → ? product is
reagent
|
OH
(a.) CH3 − CH2 − CH2 − C − CH3

||
O
(b.) CH3 − CH = CH − C − CH3
||
O
(c.) CH3 − CH2 − CH2 − CH − CH3

|
OH
(d.) CH3 − CH2 − COOH
ANSWER: b
EXPLANATION: (b)
Jones reagent oxidises 1° alcohols to aldehydes and 2° alcohols to ketones

without affecting C = C doubled bond.
#QID# 43552
(139.) The compound which reacts fastest with Lucas reagent at room
temperature is
(a.) 1-butanol
(b.) 2-butanol
(c.) 2-methylpropanol
(d.) 2-methylpropan-2-ol
ANSWER: d
#QID# 43555
(140.) Absolute alcohol is prepared by
(a.) Vacuum distillation
(b.) Azeotropic distillation
(c.) Steam distillation
ANSWER: b
EXPLANATION: (b)
Absolute alcohol is 100% pure ethanol. The fractional distillation of aqueous

solution of ethanol gives a constant boiling azeotropic mixture which contains
95% ethanol. To get 100% ethanol, a small amount of benzene is added with
azeotropic mixture and then distilled. It is called azeotropic distillation.
#QID# 43532
(141.) Consider the following reaction,
C2 H5 OH + H2 SO4 → Product
Among the following, which one cannot be formed as a product under any
conditions?
(a.) Ethyl hydrogen sulphate
(b.) Ethylene
(c.) Acetylene
(d.) Diethyl ether
ANSWER: c
EXPLANATION: (c)
(a), (b), (d) may be formed but (c) is never formed Hence, correct choice→(c).
#QID# 43675
(142.) In the following reaction, X and Y respectively are
KMnO4 /H+ 𝑌
C2 H5 OH → 𝑋→ CH3 CO2 C2 H5
H2 SO4 /Δ
(a.) CH3 OH, C2 H5 OH
(b.) CH3 CHO, CH3 OH
(c.) CH3 CO2 H, C2 H5 OH
(d.) C2 H4 , CH3 CO2 H
ANSWER: c
EXPLANATION: (c)
KMnO4 /H4 C2 H5 OH(Y)

C2 H5 OH + [O]→ CH3 COOH → CH3 COOC2 H5
H2 SO4 /Δ
ethanol (X) (esterification) ethyl ethanoate
ethanoic acid
Hence, 𝑋 = 𝐶𝐻3 𝐶𝑂𝑂𝐻
𝑌 = 𝐶2 𝐻5 𝑂𝐻
#QID# 43575
(143.) When ethyl alcohol is heated with conc.H2 SO4 , the product obtained is
(a.) CH3 COOC2 H5
(b.) C2 H2
(c.) C2 H6
(d.) C2 H4
ANSWER: d
EXPLANATION: (d)
When ethyl alcohol is heated with conc. H2 SO4 at 160° − 170℃ , the product
obtained is ethylene (C2 H4 ).
CH3 − CH2 OH + H2 SO4 → CH3 CH2 HSO4 + H2 O
ethyl hydrogen sulphate
160−170℃
CH3 – CH2 HSO4 → CH2 = CH2 + H2 SO4
Δ
ethylene
But at lower temperature ether is formed.
#QID# 43681
(144.) The conversion of m-nitrophenol to resorcinol involves respectively
(a.) Hydrolysis, diazotization and reduction
(b.) Diazotization, reduction and hydrolysis
(c.) Hydrolysis, reduction and diazotization
(d.) Reduction, diazotization and hydrolysis
ANSWER: a
#QID# 43658
(145.) The end product of which of the following reaction is isomer of alcohols?
B2 𝐻6 H2 O2
(a.) C2 H4 → 𝐴 → 𝐵
NaOH
Ag
Δ 𝐷𝑖𝑙.H2 SO4 Reduction
(b.) CHI3 → 𝐴 → 𝐵 → 𝐶
Hg+
𝐻𝐼 Aqueous KOH Conc.H2 SO4

(c.) C2 H4 → 𝐴 → 𝐵 → 𝐶
140℃
CH2 O H2 O
(d.) CH3 MgBr→ 𝐴→ 𝐶
ANSWER: c
EXPLANATION: (c)
Note: Ethers are functional isomers of alcohols
#QID# 43635
(146.) The best method to prepare cyclohexene from cyclohexanol is by using
(a.) Conc. HCI + ZnCI2
(b.) Conc. H3 PO4
(c.) HBr
(d.) Conc. HCI
ANSWER: b
EXPLANATION: (b)
The best method to prepare cyclohexene from cyclohexanol is by conc. H3 PO4

because in given options dehydrating agent is conc. H3 PO4 .
#QID# 43612
(147.) Oxygen containing organic compound upon oxidation forms a carboxylic
acid as the only organic product with its molecular mass higher by 14 units.
The organic compound is
(a.) An aldehyde
(b.) A primary alcohol

(c.) A secondary alcohol
(d.) A ketone
ANSWER: b
EXPLANATION: (b)
Because the difference in mass between – CH2 OH group and – COOH group is 14,
thus the compound which undergoes oxidation is a primary alcohol. (-CH2 OH is
the functional group of primary alcohols).
𝑅CH2 OH → 𝑅COOH
(R+31) (R+45)
Primary alcohol acid
#QID# 43595
(148.) To distinguish between salicylic acid and phenol one can use
(a.) NaHCO3 solution
(b.) 5% NaOH solution
(c.) Neutral FeCI3
(d.) Bromine water
ANSWER: a
EXPLANATION: (a)
Salicylic acid +NaHCO3 →effervescence of CO2

Phenol +NaHCO3 →No reaction
∴ NaHCO3 is used to distinguish between phenol and salicylic acid.
#QID# 43549
(149.) Four hydroxy compounds have functional groups as shown
|
(𝐴) − CH2 OH(𝐵) − CHOH(𝐶 )ϕ − OH (𝐷)ϕ − CHOH
|
The purple colour with FeCl3 will be given by
(a.) 𝐴 only
(b.) 𝐴 and 𝐵
(c.) 𝐶 only
(d.) 𝐴, 𝐵, 𝐶 and 𝐷
ANSWER: c
EXPLANATION: (c)
Phenol gives violet colouration with ferric chloride solution due to the formation
of a coloured iron complex, which is a characteristic to the existence of keto-enol
tautomerism in phenols
#QID# 43698
(150.) Picric acid is
(a.)
(b.)
(c.)
(d.)
ANSWER: c
EXPLANATION: (c)
2, 4, 6-trinitrophenol is called picric acid
#QID# 43529
(151.) By heating phenol with chloroform in alkali, it is converted into
(a.) Salicylic acid
(b.) Salicyladehyde
(c.) Anisole
(d.) Phenyl benzoate

ANSWER: b
EXPLANATION: (b)
Reimer-Tiemann Reaction In this reaction phenol reacts with chloroform and

alkali to form salicyladehyde.
#QID# 43741
(152.) Ethyl alcohol can be prepared from Grignard reagent by the reaction of
(a.) HCHO
(b.) 𝑅2 CO
(c.) RCN
(d.) RCOCI
ANSWER: a
EXPLANATION: (a)
(𝑅Mg𝑋) + HCHO → 1°alcohol

Grignard
reagent
(𝑅Mg𝑋) + 𝑅CHO → 2°alcohol
(𝑅Mg𝑋) + 𝑅CO𝑅 → 3°alcohol
#QID# 43509
(153.) Which of the following represents the Dow process for the manufacture of
phenol?
(a.)
(b.)
(c.)
ANSWER: a
EXPLANATION: (a)
By Dow process large quantities of phenol are formed by heating chlorobenzene

with a 10% solution of caustic soda or sodium carbonate at 300℃ under very
high pressure (200 atm)
#QID# 43764
(154.) Which is obtained on treating phenol, with dilute HNO3 ?
(a.)
(b.)
(c.)
(d.) None of these
ANSWER: c
EXPLANATION: (c)
−𝑂𝐻 group is an activating group, hence increase electron density on o-and p-

position in benzene ring. Thus, phenol very easily undergoes nitration
(electrophilic substitution and give trinitrophenol, i.e., picric acid).
#QID# 43572
(155.) Amongst the following, HBr reacts fastest with
(a.) Propane-1-ol
(b.) Propane-2-ol
(c.) 2-methyl propane-1-ol
(d.) 2-methyl propane-2-ol
ANSWER: d
EXPLANATION: (d)
𝑅OH + HBr → 𝑅 − Br + H2 O
The rate of reaction is fastest for 3° alcohol.
The rate of reaction decreases as fallows
3° > 2° > 1°
#QID# 43721
(156.) Pyroligneous acid doesn’t contain
(a.) Acetic acid
(b.) C2 H5 OH
(c.) CH3 OH
(d.) CH3 COCH3
ANSWER: b
EXPLANATION: (b)
Pyroligneous acid is used for the preparation of acetic acid. It contains about 10%
acetic acid, and was originally treated by neutralising with lime and then distilling
off the volatile compounds like methanol and acetone
#QID# 43592
(157.) Phenol is more acidic than alcohol because
(a.) Phenol is more soluble in polar solvents

(b.) Alcohol does not lose hydrogen atom
(c.) Phenoxide ion is stabilised by resonance
(d.) Phenoxide ion doesn’t exhibit resonance
ANSWER: c
EXPLANATION: (c)
Due to resonance the phenoxide ion is more stable whereas resonance is not
possible in alkoxide ion.
𝑅 − O⊖ no resonance is possible,
Since, phenoxide ion is better stabilized by resonance, the phenol has more
tendency to form phenoxide ion by releasing H + ion. So, phenols are acidic in
nature.
#QID# 43492
(158.) Which reaction will occurs?
(a.)
(b.)
(c.)
(d.) None of these
ANSWER: c
#QID# 43615
(159.) A simple method to remove peroxides from ethes is to treat them with an
aqueous solution of
(a.) KI
(b.) KCNS
(c.) Na2 S2 O3
(d.) Br2
ANSWER: a
EXPLANATION: (a)
Ether peroxide oxidises KI into I2 and itself gets reduced to ether. Therefore, KI
is added to remove peroxides from ethers.
2I − → I2 + 2𝑒 −
Ether peroxide+2𝑒 − → ether + O2
#QID# 43638
Cl2 3Cl2
(160.) CH3 CH2 OH → CH3 CHO → Cl3 CCHO
step−1 step−2
In above reactions the role of Cl2 in step-1 and step-2 respectively is
(a.) Oxidation, chlorination
(b.) Reduction, chlorination
(c.) Oxidation, addition
(d.) Reduction, substitution
ANSWER: a
EXPLANATION: (a)
Cl2
CH3 CH2 OH → CH3 CHO
Step 1
The above reaction is an example of oxidation. Due to oxidation – CH2 OH group
is oxidised to – CHO group.
3Cl2
CH3 CHO → Cl3 . C. CHO
Step 2
In the second step chlorination takes place. In chlorination hydrogen atom
changes by chlorine.
#QID# 43738
(161.) Glycerol is oxidised by bismuth nitrate to produce
(a.) Oxalic acid
(b.) Mesooxalic acid

(c.) Glyceric acid
(d.) Glyoxalic acid
ANSWER: b
#QID# 43695
𝑋
(162.) Phenol → forms a tribromo derivative “X ” is
(a.) Bromine in benzene
(b.) Bromine in water
(c.) Potassium bromide solution
(d.) Bromine in carbon tetrachloride at 0℃
ANSWER: b
#QID# 43718
(163.) Which of the following reagent will convert glycerol to acrolein?
(a.) P2 O5
(b.) Conc.H2 SO4
(c.) KHSO4
(d.) All of these

ANSWER: d
#QID# 43761
(164.) Ether on reacting with P2 S5 form
(a.) Diethyl sulphide
(b.) Thioalcohol
(c.) Thioether
(d.) Thioaldehyde
ANSWER: c
EXPLANATION: (c)
Ether on reacting with P2 S5 form thioether

5𝑅 − O − 𝑅 + P2 S5 → 5𝑅 − S − 𝑅 + P2 O5
ether thioether
#QID# 43618
(165.) When benzene sulphonic acid and p-nitrophenol are treated with NaHCO3 ,
the gases released respectively are
(a.) SO2 , NO2
(b.) SO2 , NO
(c.) SO2 , CO2

(d.) CO2 , CO2
ANSWER: d
EXPLANATION: (d)
Benzene sulphonic acid and p-nitro phenol react with NaHCO3 and evolve CO2
gas.
Because benzene sulphonic acid p-nitrophenol are stronger acids, so they are
capable to evolve CO2 with NaHCO3 .
HCO− +
3 + H → H2 O + CO2 ↑
acid
#QID# 43758
(166.)
is an example of
(a.) 1, 2-addition of HCl followed by tautomerism
(b.) 1, 2-addition followed by reduction
(c.) 1, 4-addition followed by tautomerism

(d.) 1, 4-addition followed by oxidation
ANSWER: c
#QID# 43512
(167.) Phenol is soluble in water because
(a.) Of weak hydrogen bonding between phenol and water molecules
(b.) Of intermolecular hydrogen bonding between phenol molecules
(c.) If has a higher boiling point than that of water
ANSWER: a
#QID# 43535
(168.) 1-propanol and 2-propanol can be distinguished by
(a.) Oxidation with alkaline KMnO4 followed by reaction with Fehling

solution
(b.) Oxidation with acidic dichromate followed by reaction with Fehling

solution
(c.) Oxidation by heating with copper followed by reaction with Fehling

solution
(d.) Oxidation with concentrated H2 SO4 followed by reaction with Fehling

solution
ANSWER: c
EXPLANATION: (c)
Catalytic dehydrogenation involves the passing of vapours of alcohol over

reduced copper at 300℃ and the product thus formed is identified.
Primary alcohols gives aldehyde while secondary alcohols give ketones
#QID# 43501
(169.) The compound on dehydrogenation gives a ketone. The original compound
is
(a.) Primary alcohol
(b.) Secondary alcohol
(c.) Tertiary alcohol
(d.) Carboxylic acid
ANSWER: b
EXPLANATION: (b)
Secondary alcohols on dehydrogenation with Cu at 573 K give ketones.
#QID# 43521
(170.) Formation of diethyl ether form ethanol is based on a
(a.) Dehydration reaction

(b.) Dehydrogenation reaction
(c.) Hydrogenation reaction
(d.) Homolytic fission reaction
ANSWER: a
EXPLANATION: (a)
Ethanol on dehydration in presence of conc. H2 SO4 at 140℃, gives diethyl ether.

Conc.H2 SO4
2C2 H5 OH→ C2 H5 − O − C2 H5 + H2 O
140℃
Diethyl ether
#QID# 43647
(171.) Among the following, which is least acidic?
(a.) Phenol
(b.) o-cresol
(c.) p-nitrophenol
(d.) p-chlorophenol
ANSWER: b
EXPLANATION: (b)
When an electron attracting group (like – NO2 , −CI) is attached to the phenol ring,
it stabilises the negative charge on the oxygen of phenoxide ion. Due to this
reason acidic character of phenol increases. But when an electron donating group
(like – CH3 ) is attached to the phenol ring, it destabilises the ring and hence, acidic
character of phenol decreases. Thus, the correct order of acidic character is
p- nitrophenol > p-chlorophenol > phenol > o-cresol.
#QID# 43561
(172.) The product A is
(a.)
(b.)
(c.)
(d.)
ANSWER: b
#QID# 43730
(173.) Catalytic dehydrogenation of a primary alcohol gives a
(a.) Secondary alcohol
(b.) Aldehyde
(c.) Ketone
(d.) Ester
ANSWER: b
EXPLANATION: (b)
Primary alcohols get dehydrogenated with reduced copper at 573 K, to give

corresponding aldehydes.
Cu,573 K
𝑅 − CH2 OH → 𝑅 − CHO + H2
primary alcohol aldehyde
#QID# 43667
(174.) Phenol is heated with a solution of mixture of KBr and KBrO3 . The major
product obtained in the above reaction is
(a.) 2-bromophenol
(b.) 3-bromophenol
(c.) 4-bromophenol
ANSWER: d
EXPLANATION: (d)
Br2 is formed by a redox reaction :
5Br − + BrO− +
3 + 6H → 3Br2 + 3H2 O
-OH group is the activating group and there is SE at o-and p-positions giving
yellowish white precipitate of 2, 4, 6-tribromophenol :
#QID# 43564
(175.) 2-methyl-2-butanol on treatment with HCl gives predominantly
(a.) 2-chloro-3-methylbutane
(b.) 2,2-dimethylpentane
(c.) 2-chloro-2-methylbutane
(d.) 1-chloro-2-methylbutane
ANSWER: c
#QID# 43604
(176.) Which of the following compounds when heated with CO at 150℃ and 500
atm pressure in presence of BF3 forms ethyl propionate?
(a.) C2 H5 OH
(b.) CH3 OCH3

(c.) C2 H5 OC2 H5
(d.) CH3 OC2 H5
ANSWER: c
EXPLANATION: (c)
Diethyl ether when hated with CO at 150℃ and 500 atm pressure in presence of
BF3 forms ethyl propionate.
#QID# 43541
(177.) The reaction of ethanol with concentrated H2 SO4 at room temperature
gives
(a.) CH3 CH2 OH2+ HSO−

4
(b.) CH3 CH2 OSO2 OH
(c.) CH3 CH2 OCH2 CH3
(d.) H2 C = CH2
ANSWER: b
EXPLANATION: (b)
When one H2 SO4 reacts with ethyl alcohol at room temperature, ethyl hydrogen
sulphate is formed
CH3 CH2 OH + H2 SO4 → CH3 CH2 HSO4 + H2 O
Room temp
Ethyl hydrogen
sulphate
#QID# 43710
(178.) The dehydration of butane-1-ol gives
(a.) 1-butene as the main product
(b.) 2-butene as the main product
(c.) Equal amounts of 1-butene and 2-butene
(d.) 2-methyl propene
ANSWER: b
EXPLANATION: (b)
The dehydration of 1-butanol gives 2-butene as the main product because 2-

carbocation is stabler than1°.
#QID# 43498
(179.) Which of the following is not cleaved by HlO4 ?
𝐴. Glycerol 𝐵. Glycol
𝐶. Propan-1,3-diol 𝐷. Methoxy-2-propanol
(a.) 𝐴, 𝐵, 𝐶, 𝐷
(b.) 𝐴, 𝐵
(c.) 𝐵, 𝐶
(d.) 𝐶, 𝐷
ANSWER: d
#QID# 43581
(180.) In the following compounds the order of acidic strength is
(a.) III > IV > I > II
(b.) I > IV > III > II
(c.) II > I > III > IV
(d.) IV > III > I > II
ANSWER: d
EXPLANATION: (d)
+𝑅 group present in phenol decreases the acidity while – 𝑅 group presents at

𝑜𝑟𝑡ℎ𝑜 or at 𝑝𝑎𝑟𝑎 position increases the acidity of phenols. Thus, the correct order
of acidity is
#QID# 43687
(181.) When compound X is oxidised by acidified potassium dichromate,
compound Y is formed. Compound Y on reduction with LiAlH4 gives X. X
and Y respectively are
(a.) C2 H5 OH, CH3 COOH
(b.) CH3 COCH3 , CH3 COOH
(c.) C2 H5 OH, CH3 COCH3
(d.) CH3 CHO, CH3 COCH3
ANSWER: a
EXPLANATION: (a)
When ethyl alcohol is oxidised by acidified potassium dichromate, CH3 COOH(Y)

is obtained as
3C2 H5 OH + 2K 2 Cr2 O7 + 8H2 SO4
→ 3CH3 COOH + 2Cr2 (SO4 )3 + 2K 2 SO4 + 11H2 O
X Y
Carboxylic acid undergoes reduction with LiAlH4 to give primary alcohol as
#QID# 43518
(182.) Salicyl aldehyde is obtained when phenol is heated with CHCl3 and
aqueous NaOH. This reaction is known by which name?
(a.) Carbyl amine reaction

(b.) Hofmann’s reaction
(d.) Kolbe-Schmidt reaction
ANSWER: c
EXPLANATION: (c)
In Reimer-Tiemann reaction Salicyladehyde is obtained when phenol is heated

with CHCl3 and aq NaOH.
#QID# 43624
(183.) Which of the following reactions will not yield 𝑝-tert butylphenol?
(a.) CH3
|
H+
Phenol +CH3 − C = CH2 →
H+
(b.) Phenol +(CH3 )3 COH→
AlCl3
(c.) Phenol +(CH3 )3 C. Cl →
NaOH
(d.) Phenol +CHCl3 →
ANSWER: d
EXPLANATION: (d)
Phenol, on refluxing with chloroform and sodium hydroxide followed by

hydrolysis yields 𝑜-hydroxy benzaldehyde
#QID# 43584
(184.) Primary, secondary and tetiary alcohols are distinguished from one another
by
(a.) Ninhydrin test
(b.) Tollen’s reagent
(c.) Lucas test
(d.) Wittig reaction
ANSWER: c
EXPLANATION: (c)
Primary, secondary and tertiary alcohols are distinguished by Lucas test. A

mixture of anhydrous ZnCl2 +conc HCl is called Lucas reagent.
#QID# 43747
(185.) The acidic character of 1°, 2°, 3° alcohols, H2 O and 𝑅C ≡ CH is of the order
(a.) H2 O > 1° > 2° > 3° > 𝑅C ≡ CH
(b.) 𝑅C ≡ CH > 3° > 2° > 1° > H2 O
(c.) 1° > 2° > 3° > H2 O > 𝑅C ≡ CH
(d.) 3° > 2° > 1° > H2 O > 𝑅C ≡ CH
ANSWER: a
EXPLANATION: (a)
Alcohols are more acidic than alkynes but less acidic than water thus, the correct
order of acidity is
H2 O > 1° > 2° > 3° > 𝑅C ≡ CH
#QID# 43704
(186.) An organic compound ‘X ’ with molecular formula, C7 H8 O is insoluble in
aqueous NaHCO3 but dissolves in NaOH. When treated with bromine water
‘X ’ rapidly gives ‘Y ’ C7 H5 OBr3.
The compounds ‘X ’ and ‘Y ’ respectively, are
(a.) Benzyl alcohol and 2, 4, 6-tribromo-3-methoxy benzene
(b.) Benzyl alcohol and 2, 4, 6-tribromo-3-methyl phenol
(c.) o-cresol and 3, 4, 5-tribromo-2-methyl phenol
(d.) Methoxybenzene and 2, 4, 6-tribromo-3-methoxy benzene
ANSWER: c
EXPLANATION: (c)
Compound ‘X ’ (C7 H8 O) is insoluble in aqueous NaHCO3 but soluble in NaOH,
so it is a phenol. Since, the number of carbon atoms remains the same after
bromination, the compound must be meta cresol and reactions takes place as
follows
#QID# 43621
(187.) When ethylene glycol is heated with a mixture of concentrated HNO3 and
concentrated H2 SO4 , it produces
(a.) COOH
|
COOH
(b.) CO2 + H2
(c.) CH2 ONO2

|
CH2 ONO2
(d.) CH2 ONO2

|
CH2 OH
ANSWER: c
#QID# 43664
(188.) Which one of the following will most readily be dehydrated in acidic
condition?
(a.)
(b.)
(c.)
(d.)
ANSWER: a
#QID# 43538
(189.) Williamson’s synthesis is used for the preparation of
(a.) Acid
(b.) Ester
(c.) Ether
(d.) Alcohol
ANSWER: c
EXPLANATION: (c)
Williamson’s synthesis is used for the preparation of ethers.

Williamson′ s
→ ′
𝑅Cl + NaO𝑅 synthesis 𝑅 − O − 𝑅 ′ + NaCI
ether
#QID# 43601
(190.) Ethyl chloride is converted into diethyl ether by
(a.) Perkins reaction
(b.) Grignard reagent
(c.) Wurtz reaction
(d.) Williamson’s synthesis
ANSWER: d
EXPLANATION: (d)
By Williamson’s synthesis, alkyl halide on reaction with sodium alkoxide gives

ether.
#QID# 43644
(191.) Which of the following will not react with NaOH?
(a.)
(b.) C2 H5 OH
(c.) CH3 CONH2
(d.) CH(CN)3
ANSWER: b
EXPLANATION: (b)
C2 H5 OH (Ethanol) is a very weak acid, hence it does not react with NaOH.
However, it reacts with metallic sodium.
#QID# 43707
(192.) Etherates are
(a.) Ethers
(b.) Solution in ether
(c.) Complexes of ethers with Lewis acid
(d.) Complexes of ethers with Lewis base
ANSWER: c
EXPLANATION: (c)
Etherates are complexes of ethers with Lewis acid
#QID# 43578
(193.) The products obtained when benzyl phenyl ether is heated with HI in the
mole ratio 1:1 are
I Phenol
II Benzyl alcohol
III Benzyl iodide
IV Iodobenzene
(a.) 1 and 3 only
(b.) 3 and 4 only
(c.) 1 and 4 only
(d.) 2 and 4 only
ANSWER: a
EXPLANATION: (a)
Benzyl phenyl ether is an unsymmetrical ether so halide ion of HI attached to the

simple alkyl group and reaction takes place by following mechanism.
1. Protonation of ether
Benzyl phenyl ether

2. Nucleophilic attack
#QID# 43727
H+
(194.) The reaction, 2CH3 CH2 ȮH → 3 CH3 CH2 OCH2 CH3 is believed to
413 K
occur through the formation of
(a.)
(b.)
(c.)
(d.) Both (b) and (c)
ANSWER: d
EXPLANATION: (d)
Alcohol is initially protonated by the acid to form protonated alcohol or oxonium

ion. It is then attacked by a second molecule of alcohol which acts as nucleophile
#QID# 43684
(195.) An organic compound ‘X ’ on treatment with pyridinium chloro chromate
in dichloromethane gives compound ‘Y ’. Compound ‘Y’,reacts with I2 and
alkali to form triiodomethane. The compound ‘X ’ is
(a.) C2 H5 OH
(b.) CH3 CHO
(c.) CH3 COCH3
(d.) CH3 COOH
ANSWER: a
EXPLANATION: (a)
PCC
C2 H5 OH + [O] → CH3 CHO
in CH2 Cl2
(X) (Y)
CH3 CHO + 4NaOH + 3I2 → CHI3 + HCOONa + 3H2 O + 3NaI
(Y)
(yellow ppt
tri-iodomethane)
#QID# 43495
(196.) The alcohol manufactured from water gas is
(a.) CH3 OH
(b.) C2 H5 OH
(c.) CH3 CH2 COOH
(d.) (CH3 )2 CHOH
ANSWER: a
EXPLANATION: (a)
Methyl alcohol (CH3 OH) is prepared by passing H2 in water gas in presence of

catalyst.
Cr2 O3 −ZnO
CO + H2 + H2 → CH3 OH
300−400℃
Water gas methyl alcohol
#QID# 43750
(197.) Among the following compounds which can be dehydrated very easily?
(a.) CH3 CH2 CH2 CH2 CH2 OH
(b.) OH
|
CH3 CH2 CH2 CHCH3
(c.) CH3
|
CH3 CH2 CCH2 CH3
|
OH
(d.) CH3 CH2 CHCH2 CH2 OH

|
CH3
ANSWER: c
EXPLANATION: (c)
Dehydration of alcohol is in order

1° < 2° < 3°
Thus, (C), a 3° alcohol is dehydrated very easily.
#QID# 43558
(198.) Phenol gives characteristic colouration with
(a.) Iodine solution
(b.) Bromine water
(c.) Aqueous FeCI3 solution
(d.) Ammonium hydroxide
ANSWER: c
EXPLANATION: (c)
Phenol gives characteristic colouration (violet) with aqueous FeCI3 solution.
#QID# 43661
Reflux
(199.) 2-propanol +NaBr→ 𝑋. What is X?
(a.) 2-bromopropane
(b.) Propane
(c.) Propene
(d.) Propanone
ANSWER: a
EXPLANATION: (a)
Reflux
CH3 − CH − CH3 + NaBr → CH3 − CH − CH3 + H2 O
Δ
| |
OH Br
2-propanol 2-bromopropane
#QID# 43744
(200.) The reaction of 𝑖𝑠𝑜-propylbenzene with oxygen in the presence of a
catalytic amount of HBr followed by treatment with an acid gives phenol.
The reaction proceeds through the intermediate formation of
(a.)
(b.)
(c.)
(d.) All of these
ANSWER: d
#QID# 43525
(201.) The reaction,
C2 H5 ONa + C2 H5 I → C2 H5 OC2 H5 + NaI is known as
(a.) Kolbe’s synthesis
(b.) Wurtz’s synthesis
(c.) Williamson’s synthesis
(d.) Grignard’s synthesis
ANSWER: c
EXPLANATION: (c)
Williamson’s synthesis It involves the heating of alkyl halide with sodium or

potassium alkoxides. This reaction is used for the preparation of ethers e.g.,
C2 H5 ONa + C2 H5 I → C2 H5 − OC2 H5 + NaI
#QID# 43502
(202.) Choose the incorrect statement
(a.) Ordinary ethyl alcohol is known as rectified spirit
(b.) The alcohol sold in the market for polishing etc, is known as methylated
spirit
(c.) Absolute alcohol is 100% ethanol
(d.) Power alcohol is 100% ethanol

ANSWER: d
EXPLANATION: (d)
Alcohols which are used for generating power is called power alcohol. A mixture
of 20% ethanol and 80% gasoline is used in internal combustion engines to derive
power
#QID# 43565
(203.) Which of the following reacts fastest with a mixture of anhydrous ZnCI2
and conc. HCI?
(a.) Trimethyl carbinol
(b.) Ethanol
(c.) Propanol
(d.) Methanol
ANSWER: a
EXPLANATION: (a)
Reactivity order of alcohols towards ZnCl2 and conc. HCl is ter. alcohol > sec
alcohol > pri alcohol
CH3
|
Trimethyl carbinol is CH3 − C − OH. It is tertiary alcohol.
|
CH3
#QID# 43608
(204.) The major product in the reaction of PhCH2 CH(OH)CH(CH3 )2 with
concentrated H2 SO4 is
(a.)
(b.)
(c.)
(d.)
ANSWER: b
#QID# 43691
(205.) Which one can differentiate between C2 H5 OH and CH3 OH?
(a.) H2 O
(b.) Na2 CO3 + I2
(c.) NH3
(d.) HCI
ANSWER: b
EXPLANATION: (b)
CH3 OH and C2 H5 OH can be differentiated by using Na2 CO3 and I2 . C2 H5 OH
gives yellow precipitate of CHI3 whereas CH3 OH does not react with it.
C2 H5 OH + 4I2 + Na2 CO3 → CHI3 + 5NaI + HCOONa + 3CO2 + H2 O
(iodoform
Yellow ppt)
#QID# 43605
(206.) In the following reaction sequence
P+𝐼2 HNO2
𝑅 − OH → 𝑅 − I→ 𝑅NO2 no reaction The alcohol is a
(d.) Phenol
ANSWER: c
EXPLANATION: (c)
In the given sequence of reaction, the alcohol is tertiary.
#QID# 43522
(207.) The reaction involved in the oil of winter green test is salicylic acid
𝛥
→ product. The product is treated with Na2 CO3 solution. The
Conc.H2 SO4
missing reagent in the above reaction is
(a.) Phenol
(b.) NaOH
(c.) Ethanol
(d.) Methanol
ANSWER: d
EXPLANATION: (d)
Methanol reacts with salicylic acid in the presence of a few drops of conc H2 SO4
to give methyl salicylate having the smell of oil of winter green.
#QID# 43645
(208.) In which of the following reactions the product is an ether?
(a.) C6 H6 + CH3 COCl/anhydrous AlCl3
(b.) C2 H5 Cl + aq. KOH

(c.) C6 H6 + C6 H5 COCl/anhydrous AlCl3
(d.) C2 H5 Cl + C2 H5 ONa
ANSWER: d
EXPLANATION: (d)
Alkyl halides react with sodium alkoxide to give ether. This is called
Williamson’s synthesis of ether.
Δ
C2 H5 Cl + C2 H5 ONa → C2 H5 OC2 H5 + NaCl
ether
#QID# 43602
(209.) Glycerol on heating with oxalic acid at 110℃ gives
(a.) Ethanol
(b.) Methanoic acid
(c.) Ether
(d.) Acetone
ANSWER: b
EXPLANATION: (b)
Glycerol react with oxalic acid at 110℃ temperature, it gives methanoic acid
(formic acid).
s
#QID# 43731
(210.) C − O − C angle would be maximum in
(a.) CH3 − O − CH3
(b.) CH3 − O − C2 H5
(c.) C2 H5 − O − C2 H5
(d.) (CH3 )2 CH − O − CH(CH3 )2
ANSWER: d
EXPLANATION: (d)
Bulkier the alkyl groups in the ether, greater is the C − O − C bond angle due to
steric factor
#QID# 43628
(211.) In fermentation by zymase, alcohol and CO2 are obtained from
(a.) Invert sugar
(b.) Glucose
(c.) Fructose
(d.) All of these
ANSWER: b
EXPLANATION: (b)
Zymase enzyme act on glucose and give ethyl alcohol and carbon dioxide.
Zymase
C6 H12 O6 → 2C2 H5 OH + 2CO2 ↑
ethyl alcohol
#QID# 43539
(212.) On boiling with concentrated hydrobromic acid, phenyl ethyl ether yields
(a.) Phenol and ethane
(b.) Phenol and ethyl bromide
(c.) Bromobenzene and ethanol
(d.) Bromobenzene and ethane
ANSWER: b
EXPLANATION: (b)
Breaking bond (i) is difficult as this bond has a partial double bond character due
to resonance
#QID# 43585
(213.) Phenol is heated with phthalic anhydride in presence of conc H2 SO4 . The
product gives pink colour with alkali. The product is
(a.) Phenolphthalein
(b.) Bakelite
(c.) Salicylic acid
(d.) Fluorescein
ANSWER: a
EXPLANATION: (a)
Phenol is heated with phthalic anhydride in presence of conc H2 SO4 to given

phenolphthalein which gives pink colour with alkali
#QID# 43711
(214.) Which substance will not react with ϕ NNCl (ϕ = Phenyl) to give dye?
(a.)
(b.)
(c.)
(d.)
ANSWER: d
EXPLANATION: (d)
will not with ϕNNCl to give dye
#QID# 43499
(215.) CH3 CH2 OH convert into CH3 CHO in the presence of
(a.) Na2 Cr2 O7 and NaOH
(b.) Na2 Cr2 O7 and dil. H2 SO4
(c.) NaOH
(d.) Fe in presence of NaOH
ANSWER: b
EXPLANATION: (b)
1°alcohol are converted into aldehyde by reaction with Na2 Cr2 O7 and H2 SO4 .
Na2 Cr2 O7 +H2 SO4
CH3 CH2 OH + [O] → CH3 CHO + H2 O
ethyl alcohol ethanal
#QID# 43582
(216.) Glycerol reacts with potassium bisulphate to produce
(a.) Allyl iodide
(b.) Allyl sulphate
(c.) Acryl aldehyde
(d.) Glycerol trisulphate
ANSWER: c
EXPLANATION: (c)
Glycerol is dehydrated on heating with KHSO4 .
#QID# 43671
(217.) The reaction of 𝑛𝑒𝑜-pentyl alcohol with concentrated HCl gives
(a.) 𝑛𝑒𝑜-pentyl chloride
(b.) 2-chloro-2-methylbutane
(c.) 2-methyl-2-butene
(d.) A mixture of 𝑛𝑒𝑜-pentyl chloride and 2-methyl-2-butene
ANSWER: b
#QID# 43625
(218.) C4 H10 O gives white precipitate within 5 min with concentrated
hydrochloric acid in the presence of amhydrous zinc chloride.
Alcohol can be
(a.)
(b.)
(c.)
(d.)
ANSWER: b
EXPLANATION: (b)
Secondary alcohols give turbidity within 5 min with Lucas reagent
#QID# 43542
(219.) Lucas test is associated with
(a.) Aldehydes
(b.) Phenols
(c.) Carboxylic acids
(d.) Alcohols
ANSWER: d
EXPLANATION: (d)
Lucas test is used to distinguish primary, secondary and tertiary alcohols.
#QID# 43754
(220.) Order of reactivity of halogen acids towards an alcohol is
(a.) HCl > HBr > HI
(b.) HBr > HI > HCl
(c.) HI > HBr > HCl
(d.) HI > HCl > HBr
ANSWER: c
EXPLANATION: (c)
Longer the bond length, lesser will be dissociation energy and hence, more
reactivity.
Among halogen acids bond length increases from HCl to HI.
∴ Order of reactivity of halogen acids towards alcohol is
HI > HBr > HCl
#QID# 43688
(221.) Which of the following reactions does not yield an ether?
(a.) Sodium methoxide reacts with dimethyl sulphate
(b.) Sodium ethoxide reacts with ethyl bromide
(c.) Sodium ethoxide reacts with bromocyclopropane
(d.) Ethanol reacts with CH2 N2 in presence of HBF4
ANSWER: c
EXPLANATION: (c)
2° alkyl halides tend to undergo elimination. Thus bromocyclopentane on

treatment with sodium ethoxide gives cyclopentane rather than cyclophenyl ethyl
ether
#QID# 43519
(222.) In Williamson’s synthesis ethoxy ethane is prepared by
(a.) Passing ethanol over heated alumina
(b.) Heating sodium ethoxide with ethyl bromide
(c.) Treating ethyl alcohol with excess of H2 SO4 at 430-440 K
(d.) Heating ethanol with dry Ag 2 O
ANSWER: b
EXPLANATION: (b)
Williamson′ s
CH3 CH2 ONa + C2 H5 Br→ CH3 CH2 OCH2 CH3 + NaBr
synthesis
Sodiumethoxide bromo ethoxyethane
ethane
#QID# 43751
(223.) In Williamson’s synthesis
(a.) An alkyl halide is treated with sodium alkoxide
(b.) An alkyl halide is treated with sodium
(c.) An alcohol is heated with conc. H2 SO4 at 130℃
ANSWER: a
EXPLANATION: (a)
Williamson’s synthesis It is the best method for the laboratory preparation of both
simple and mixed ethers and involves the action of sodium alkoxide on a suitable
alkyl halide.
C2 H5 − Br + C2 H5 ONa → C2 H5 − O − C2 H5 + NaBr
Ethyl bromide diethyl ether
C2 H5 − Cl + C6 H5 − ONa → C6 H5 − O − C2 H5 + NaCl
Ethyl phenyl ether
#QID# 43648
(224.) Methanol cannot be dried with anhydrous CaCI2 because
(a.) CaCI2 dissolves in it
(b.) It is not good dehydrating agent
(c.) It forms a solid CaCI2 . 4CH3 OH
(d.) It reacts with CH3 OH
ANSWER: c
EXPLANATION: (c)
Methanol cannot dried with anhydrous CaCl2 because it forms a solid

CaCl2 . 4CH3 OH(addition compound).
#QID# 43705
(225.) In which case, methyl t-butyl ether is formed?
(a.) (C2 H5 )3 CONa + CH3 Cl
(b.) (CH3 )3 CONa + CH3 Cl

(c.) (CH3 )3 CONa + C2 H5 Cl
(d.) (CH3 )2 CHONa + CH3 Cl
ANSWER: b
EXPLANATION: (b)
When, sod. tert-butoxide is reacted with methyl chloride, methyl t-butyl ether is
formed.
#QID# 43748
(226.) Consider the reaction,
𝐴 and 𝐵 respectively are
(a.) 1, 2-epoxycyclohexane, 𝑡𝑟𝑎𝑛𝑠-2-bromocyclohexanol
(b.) 1, 2-epoxycyclohexane, 𝑐𝑖𝑠-2- bromocyclohexanol
(c.) 𝑡𝑟𝑎𝑛𝑠-2 bromocyclohexanol 1,2-epoxyethane
(d.) 𝑐𝑖𝑠-2- bromocyclohexanol 1,2-epoxyethane
ANSWER: a
EXPLANATION: (a)
𝐴 = 1,2-epoxycyclohexane
𝐵 = 𝑡𝑟𝑎𝑖𝑛𝑠-2-bromocyclohexanol
#QID# 43708
(227.) In the Liebermann test for phenols, the blue or green colour produced is
due to the formation of
(a.)
(b.)
(c.)
(d.)
ANSWER: d
EXPLANATION: (d)
Phenol gives Libermann’s nitroso reaction.

NaNO2 NaOH
Phenol in Conc. H2 SO4 → Red colour → Blue colour
excess of water (Excess)
This blue colour is formed due to the formation of
#QID# 43665
(228.) Which doesn’t form in the acid catalysed rearrangement of cumene
hydroperoxide?
(a.)
(b.)
(c.)
(d.)
ANSWER: d
EXPLANATION: (d)
In rearrangement of cumene hydroperoxide
is not formed
#QID# 43685
(229.) Ketone upon treatment with Grignard reagent gives

(d.) Aldehyde
ANSWER: c
EXPLANATION: (c)
Ketones give an addition product having more number of carbon atoms with
Grignard reagent, which on hydrolysis gives an alcohol (3°).
Formaldehyde gives primary alcohol with Grignard reagent while any other
aldehyde except formaldehyde give secondary alcohol.
#QID# 43728
(230.) For the sequence of reaction,
C2 H5 MgI H2 O/H+
𝐴→ 𝐵→ 𝑡𝑒𝑟𝑡 − pentyl alcohol.
The compound A in the sequence is
(a.) 2-butanone
(b.) Acetaldehyde
(c.) Acetone
(d.) Propanal
ANSWER: c
#QID# 43622
(231.) Alcohol (CH3 )2 CHCH2 OH cannot be obtained by
(a.) HCHO + (CH3 )2 CHCH2 Mg𝑋
(b.)
(c.) (CH3 )2 CHCH2 CH2 Mg𝑋 + O2 air
(d.) (CH3 )2 CHCHO + CH3 Mg𝑋
ANSWER: d
#QID# 43676
(232.) The final product of the following reaction is/are
(a.)
(b.)
(c.)
(d.)
ANSWER: b
EXPLANATION: (b)
Phenol on reaction with chloroform and KOH gives salicyladehyde, which with
50% KOH solution undergoes Cannizaro’s reaction.
#QID# 43633
(233.) Ethylene glycol reacts with excess of PCI5 to give
(a.) 1, 1-dichloroethane
(b.) 1, 2-dichloroethane
(c.) 1, 1, 1-trichloroethane
(d.) 2, 2-dichloroethane
ANSWER: b
EXPLANATION: (b)
Ethylene glycol reacts with excess of PCl5 to give ethylene chloride.
#QID# 43547
(234.) When phenyl magnesium bromide reacts with t-butanol, the product would
be
(a.) Benzene
(b.) Phenol
(c.) t-butyl benzene
(d.) t-butyl phenyl ether
ANSWER: a
EXPLANATION: (a)
Phenyl magnesium bromide reacts with t-butanol to produce benzene because

phenyl group (electronegative group) is associated with active hydrogen of
alcohol, i.e., −H of – OH group of alcohol.
C6 H5 MgBr + (CH3 )3 C − OH → C6 H5 + (CH3 )3 CO − MgBr
#QID# 43504
(235.) Which one of the following gases is liberated when ethyl alcohol is heated
with methyl magnesium iodide?
(a.) Methane
(b.) Ethane
(c.) Carbon dioxide
(d.) Propane
ANSWER: a
EXPLANATION: (a)
Ethyl alcohol reacts with methyl magnesium iodide as follows
#QID# 43716
(236.) Which of the following is the best method for making 𝑖𝑠𝑜-propylmethyl
ether?
(a.) CH3 I + (CH3 )2 CHOH →
(b.) CH3 I + (CH3 )2 CHO− →
(c.) (CH3 )2 CHI + CH3 O− →

(d.) (CH3 )2 CHCl + CH3 OH →
ANSWER: b
#QID# 43524
(237.)
𝐴 and 𝐵 are
(a.)
(b.)
(c.)
(d.)
ANSWER: b
#QID# 43567
(238.) Benzoylation of phenol in alkaline medium is known is known as
(a.) Friedel-Crafts reaction
(b.) Wurtz-Fittig reaction
(c.) Schotten-Baumann reaction
ANSWER: d
EXPLANATION: (d)
The process of benzoylation of compounds containing active hydrogen such as

phenol, aniline, alcohol etc, with benzoyl chloride in the presence of aqueous
NaOH is called Schotten-Baumann reaction.
#QID# 43759
(239.) One mole of an organic compound A with the formula C3 H8 O reacts
completely with two moles of HI to form X and Y. When Y is boiled with
aqueous alkali it forms Z. Z answers the iodoform test. The compound A is
(a.) Propan-2-ol
(b.) Propan-1-ol
(c.) Ethoxyethane
(d.) Methoxyethane
ANSWER: d
EXPLANATION: (d)
Molecular formula C3 H8 O(C𝑛 H2𝑛+2 O)suggests that the organic compound is
either alcohol or ether.
Since, the compound on reaction with HI gives two different compounds, It must
be an unsymmetrical ether, and its formula must be CH3 OC2 H5(methoxyethane).
𝐶H3 OC2 H5 + 2HI → CH3 I + C2 H5 OH
Methoxyethane X Y
C2 H5 OH + 6NaOH + 4I2 → CHI3 + HCOONa + 5H2 O + 5NaI
Aqueous iodoform
#QID# 43653
(240.) Tertiary alcohols (3°) having at least four carbon atoms upon drastic
oxidation yield carboxylic acid with
(a.) One carbon atom less
(b.) Two carbon atoms less
(c.) Three carbon atoms less
(d.) All the above three options are correct
ANSWER: b
EXPLANATION: (b)
3°alcohols are resistant to oxidation under drastic condition. They first form
ketone and then acid by loosing one carbon at each step.
Drastic condition [O]
3° alcohol → ketone → acid
[O]
(4C) (3C) (2C)
∴Acid having 2C is formed when 3° alcohol is oxidised under drastic conditions.
#QID# 43693
(241.) Which of the following compounds is resistant to nucleophilic attack by
hydroxyl ions?
(a.) Acetamide
(b.) Methyl acetate
(c.) Diethyl ether
(d.) Acetonitrile
ANSWER: c
EXPLANATION: (c)
Diethyl ether itself being a Lewis base is not attacked by nucleophiles, 𝑖𝑒, OH −
ion. All others contain an electrophilic carbon and are readily attacked by
nucleophile
#QID# 43590
(242.) Which compound will have highest boiling point?
(a.) CH4
(b.) CH3 OH
(c.) C2 H5 OH
(d.) HCHO
ANSWER: c
EXPLANATION: (c)
The boiling point of alcohols is higher than the boiling points of corresponding
alkanes and aldehydes due to H-bonding. As the molecule mass increases, boiling
point increases.
Thus, C2 H5 OH has the higher boiling point among the given.
#QID# 43527
(243.) Ether in contact with air for a long time form peroxides. The presence of
peroxide in either can be tested by adding Fe2+ ion and then adding
(a.) KCN
(b.) SnCl2
(c.) HgCl2
(d.) KCNS
ANSWER: d
EXPLANATION: (d)
Peroxide will oxidise Fe2+ to Fe3+ which gives a blood red colour with KCNS.
O2−
2 + 2Fe
2+
+ 4H + → 2Fe3+ + 2H2 O
Fe3+ + 3KCNS → Fe(CNS)3 + 3K +
(blood red colour)
#QID# 43696
(244.) Which of the following is not soluble in NaHCO3 solution?
(a.)
(b.)
(c.)
(d.)
ANSWER: c
EXPLANATION: (c)
is not soluble in NaHCO3
#QID# 43587
(245.) By which of the following procedures can ethyl 𝑛-propyl ether be
obtained?
HBr Mg H2 O Na
(a.) C2 H5 OH → I→ II → III →
ether CH3 CH2 Br
HBr Mg 1.CH2 O Na
(b.) C2 H5 OH → I→ II → III →
ether 𝐻3 𝑂+ CH3 CH2 Br
140℃
(c.) C2 H5 OH + H2 SO4 →
1800 C CH3 CH2 CH2 Br

(d.) C2 H5 OH + Conc. H2 SO4 → I→
ANSWER: b
#QID# 43544
(246.) Which of the following is dihydric alcohol?
(a.) Glycerol
(b.) Ethylene glycol
(c.) Catechol
(d.) Resorcinol
ANSWER: b
EXPLANATION: (b)
Glycols are dihydric alcohols (having two hydroxyl groups). Ethylene glycol is
the first member of this series.
CH2 OH
|
CH2 OH
ethylene glycol
#QID# 43650
(247.) Phenol can be converted to o-hydroxybenzaldehyde by
(a.) Kolbe’s reaction
(b.) Reimer-Tiemann reaction
(c.) Wurtz reaction
(d.) Cannizaro reaction
ANSWER: b
EXPLANATION: (b)
(Reimer-Tiemann’s reaction)
#QID# 43736
(248.) C2 H5
|
To prepare ϕ − C − C2 H5 by 𝑅Mg𝑋 which is the incorrect pair?
|
OH
(a.) ϕ MgBr + (C2 H5 )2 CO →

H2 O
(b.)
(c.) C2 H5 MgBr + ϕCOCH2 CH3 →

H2 O
(d.) ϕMgBr + C2 H5 COCH3 →
H2 O
ANSWER: d
#QID# 43610
(249.) Which is correctly matched?
Alcohol α-H β-H Colour in Victor Meyer test
A.) X 3 0 Colourless
B.) Y 1 6 Blue
C.) Z 0 9 Red
(a.) 𝐴 and 𝐵
(b.) 𝐵 and 𝐶
(c.) Only 𝐶
(d.) Only 𝐵
ANSWER: d
EXPLANATION: (d)
Secondary alcohols give blue colour in Victor Meyer test
#QID# 43733
(250.) Carbolic acid is
(a.) HCOOH
(b.) CH3 COOH

(c.) C6 H5 COOH
(d.) C6 H5 OH
ANSWER: d
EXPLANATION: (d)
Phenol (C6 H5 OH) is carbolic acid.
#QID# 43607
(251.) An organic compound C3 H6 O neither gives precipitate with semicarbazide
nor reacts with sodium. It could be
(a.) CH3 CH2 CHO
(b.) CH3 COCH3
(c.) CH2 = CHCH2 OH
(d.) CH2 = CHOCH3
ANSWER: d
EXPLANATION: (d)
Alcohols (−OH) react with sodium and carbonyl compounds give

precipitate with semicarbazide.
Since, the compound with molecular formula, C3 H6 O does not give precipitate
with simicarbazide and does react with sodium, it is neither a carbonyl compound
nor an alcohol. Hence, it must be an ether, i.e., CH2 = CHOCH3
#QID# 43690
CH3 MgBr
(252.) Ethyl ester → 𝑃. The product 𝑃 will be
excess
(a.)
(b.)
(c.)
(d.)
ANSWER: a
#QID# 43756
(253.) The correct order of the solubility of different alcohols in water is
(a.) Ethanol > 𝑛-propanol > 𝑛-butyl alcohol
(b.) 𝑛-propyl alcohol > ethyl alcohol > 𝑛-butyl alcohol
(c.) ethyl alcohol > 𝑛-butyl alcohol > 𝑛-propyl alcohol
(d.) 𝑛-butyl alcohol > 𝑛-propyl alcohol > ethyl alcohol

ANSWER: a
EXPLANATION: (a)
Solubility of alcohols in water decreases as the size of alkyl group increases

because tendency to form hydrogen bonding decreases. So, the order of solubility
is as
Ethanol > 𝑛-propanol > 𝑛-butyl alcohol
#QID# 43627
(254.) Some time explosion occurs while distilling ethers. It is due to the presence
of
(a.) Oxide
(b.) Ketones
(c.) Aldehyde
(d.) Peroxides
ANSWER: d
EXPLANATION: (d)
In presence of air and light, ether form peroxides which cause explosion during
distillation
#QID# 43753
(255.) The major product obtained on interaction of phenol with sodium
hydroxide and carbon dioxide is
(a.) Benzoic acid
(b.) Salicyladehyde
(c.) Salicylic acid
(d.) Phthalic acid
ANSWER: c
#QID# 43670
(256.) Strength of acidity is in order
(a.) II > I > III > IV
(b.) III > IV > I > II
(c.) I > IV > III > II
(d.) IV > III > I > II
ANSWER: b
EXPLANATION: (b)
Proton donors are acids. The acidity of phenol increases by presence of electron
withdrawing groups (e.g.,−NO2 group) because these groups weaken the O − H
bond and stabilise the phenoxide by resonance. More the number of electron
withdrawing group in compound more will be acidity. On the other hand electron
donating group (e.g., CH3 ) decrease the acidity of phenol because they strengthen
the O − H bond.
Therefore, correct order of acidity is
III > IV > I > II
#QID# 43713
(257.) The following reaction is known as
(a.) Perkin reaction
(b.) Gattermann reaction
(c.) Kolbe reaction
(d.) Gattermann-aldehyde reaction
ANSWER: d
EXPLANATION: (d)
In the presence of anhydrous ZnCl2 , phenol form salicyladehyde. It is

Gattermann-aldehyde reaction.
#QID# 43550
(258.) The order of reactivity of the following alcohols
(a.) I > 𝐼𝐼 > 𝐼𝐼𝐼 > 𝐼𝑉
(b.) I > 𝐼𝐼𝐼 > 𝐼𝐼 > 𝐼𝑉
(c.) IV > 𝐼𝐼𝐼 > 𝐼𝐼 > 𝐼
(d.) IV > 𝐼𝐼𝐼 > 𝐼 > 𝐼𝐼
ANSWER: c
EXPLANATION: (c)
The order of reactivity depends upon the stability of the carbocation formed
+ + + +
𝑖𝑒, FCH2 HCH3 , FCH2 CH2 HCH3 , CH3 HCH3 and Ph H2 . The stability order
C C C C
+ + + +
of carbocations is Ph H2 > 𝐶H3 HCH3 > 𝐹𝐶H2 CH2 HCH3 > 𝐹𝐶H2 HCH3 .
C C C C
Thus, the order of reactivity follows the order IV > III > II> I
#QID# 43593
(259.) The function of ZnCI2 in Lucas test for alcohols is
(a.) To act as acid catalyst and react with HCI to form H2 ZnCI4
(b.) To act as base catalyst and react with NaOH to formNa2 Zn(OH)4
(c.) To act as amphoteric catalyst
(d.) To act as neutral catalyst

ANSWER: a
#QID# 43570
(260.) Phenol, 𝑝-methylphenol, 𝑚-nitrophenol and 𝑝-nitrophenol follows order
of increasing strength as
(a.) Phenol, 𝑝-methylphenol, 𝑝-nitrophenol, 𝑚-nitrophenol
(b.) 𝑝-methylphenol, pheol, 𝑚-nitrophenol, 𝑝-nitrophenol
(c.) 𝑝-methylphenol, 𝑚-nitrophenol, phenol, 𝑝-nitrophenol
(d.) 𝑚-nitrophenol, 𝑝-nitrophenol, phenol, 𝑝-methylphenol
ANSWER: b
EXPLANATION: (b)
The order of increasing acidic strength is

𝑝-methyl phenol < phenol < 𝑚-nitrophenol < 𝑝-nitrophenol
#QID# 43530
(261.) The density of glycerol is higher than propanol due to
(a.) Van der Waals’ attraction
(b.) Hydrogen bonding
(c.) Ionic bonding
(d.) More number of covalent bonds

ANSWER: b
EXPLANATION: (b)
The density of glycerol is higher than propanol due to extensive intermolecular

hydrogen bonding. Glycerol contains three – OH groups while propanol contains
only one ∎– OH group.
#QID# 43613
(262.) When phenol is heated with phthalic anhydride and H2 SO4 , it produces
(a.) Phenol red
(b.) Methyl orange
(c.) Salicylic acid
(d.) Phenolphthalein
ANSWER: d
EXPLANATION: (d)
In the presence of conc. H2 SO4 , two molecules of phenol condense with phthalic
anhydride to form phenolphthalein
#QID# 43507
(263.) The cleavage of an aryl-alkyl ether with cold HI gives
(a.) Alkyl iodide and water
(b.) Aryl iodide and water
(c.) Alkyl iodide, aryl iodide and water
(d.) Phenol and alkyl iodine
ANSWER: d
EXPLANATION: (d)
Cold HI
C6 H5 O − 𝑅 → C6 H5 OH + 𝑅I
Aryl-alkyl ether phenol alkyl
iodide

Alcohols Phenols and Ethers

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Alcohols Phenols and Ethers

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FOR COMPLETE QUESTION BANK

CALL/WHATSAPP XELLENT – 6290457667

11. ALCOHOLS PHENOLS AND ETHERS

(d.) Both (a) and (b)

C − Br bond is weaker as compared to C − Cl bond

Molecular weight of phenol= 12 × 6 + 1 × 6 + 16 = 94

(a.) Liebermann’s reaction

(b.) Phthalein fusion test

(c.) Reimer-Tiemann reaction

(d.) Schotten-Baumann reaction

(b.) CH3 COCl

(c.) (CH3 CO)2 O

(d.) CH3 COOH

(a.) 1° > 2° > 3°

(b.) 3° > 2° > 1°

(d.) 2° > 3° > 1°

(b.) CH3 CHOHCH3

(d.) Any of these

(c.) Diphenyl ether

(d.) Diethyl ether

Diethyl sulphate in the presence of NaOH acts as alkylating agent, it causes

(c.) 3-bromophenol boric acid

Like nitration, bromination of o-or p-phenolsulphonic acid occurs with

(a.) CH3 − CH2 − I and CH3 CH2 OH

(b.) CH3 − CH2 − OH

(c.) CH3 − CH2 − I

(d.) None of the above

Ether on reaction with excess of HI produce two molecules of alkyl halide.

(a.) C2 H5 Cl, KOH (alc. ), Δ

(b.) 2C2 H5 OH, conc. H2 SO4 , 140℃

(d.) C2 H2 , dil H2 SO4 , HgSO4

Ethyl chloride reacts with sodium ethoxide to form diethyl ether as

(a.) Reimer- Tiemann reaction

(b.) Lederer-Manasse reaction

(c.) Sandmeyer reaction

(d.) Kolbe’s reaction

The products are

is not a resonating structure of 𝑝-nitrophenoxide

(b.) Dihydroxy acetone

(c.) Both(a) and (b)

(d.) None of the above

C2 H5 OH and C6 H5 OH can be distinguished by neutral FeCl3 solution or I2

(c.) Neutral FeCI3

(d.) Br2 /H2 O

Phenol cannot be distinguished from ethanol by sodium because both evolve

(c.) CH2 = CHOH

(d.) None of these

(a.) (CH3 )2 CHCH = CH2

(b.) (CH3 )2 C = CH − CH3

(c.) 1 : 1 mixture of (a) and (b)

(d.) None of the above

Many a time unexpected products result during dehydration of alcohols.

(a.) CH2 = CH − CH2 CH2 OH

(b.) CH3 − CH = CH − CH2 OH

(a.) Anhydrous AlCl3 with concentrated HCl

(c.) Anhydrous ZnCl2 and concentrated HCl

(d.) Anhydrous CaCl2 and concentrated HCl

(a.) I > II > III

(b.) III > II > I