Alcohols Phenols and Ethers
Alcohols Phenols and Ethers
Alcohols Phenols and Ethers
#QID# 43636
(1.)
Product is
(a.)
(b.)
(c.)
ANSWER: c
#QID# 43659
(2.)
(a.)
(b.)
(c.)
(d.)
ANSWER: b
EXPLANATION: (b)
#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)
#QID# 43513
NaNO2 /H2 SO4 H2 O NaOH
(4.) Phenol → 𝐵 → 𝐶 → 𝐷
Name of the above reaction is
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
ANSWER: a
#QID# 43559
(6.) The correct order of boiling point for primary (1°), secondary (2°) and
tertiary (3°)alcohols is
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
(c.) CH3
|
CH3 − C − OH
|
CH3
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
ANSWER: a
EXPLANATION: (a)
#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
(d.) 3, 5-dibromophenol
ANSWER: b
EXPLANATION: (b)
ANSWER: c
EXPLANATION: (c)
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?
ANSWER: b
EXPLANATION: (b)
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
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,
(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)
(a.) Glyceraldehyde
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)
#QID# 43533
(19.) Phenol can be distinguished from ethanol by the following reagents except
(a.) Sodium
(b.) NaOH/I2
ANSWER: a
EXPLANATION: (a)
(20.)
In the above reaction 𝐴 is
(a.)
(b.)
ANSWER: b
#QID# 43496
(21.) CH3
|
Acid
(CH3 )2 CHCHOH → 𝑋
–H2 O
The major product obtained in this reaction is
EXPLANATION: (b)
#QID# 43642
(22.) Which alcohol cannot be oxidized by MnO2 ?
(c.) ϕCH2 OH
(d.)
ANSWER: a
#QID# 43596
(23.) Lucas reagent is
ANSWER: c
#QID# 43745
(24.) The correct order of ease of dehydration of following is
ANSWER: b
EXPLANATION: (b)
#QID# 43699
(25.) What is the hybridisation of carbon and oxygen in electronic structure of
ether?
(a.) 𝑠𝑝3 and 𝑠𝑝2
(c.) 𝑠𝑝 and 𝑠𝑝
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?
(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
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
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
(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
ANSWER: b
EXPLANATION: (b)
#QID# 43656
(32.) The alcohol that produces turbidity immediately with ZnCI2 /conc. HCI at
room temperature
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
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?
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
(d.) Aspirin
ANSWER: d
#QID# 43594
(36.) Cumene process is the most important commercial method for the
manufacture of phenol. Cumene is
ANSWER: a
EXPLANATION: (a)
#QID# 43651
(37.) Correct order of dehydration of
I (b)
(c) (d)
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)
#QID# 43740
(40.) When diethyl ether is heated with an excess of PCl5 , it yields
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)
#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
(c.) C2 H5 COOC2 H5
ANSWER: c
#QID# 43568
(43.) Carbocation is not the intermediate in
ANSWER: d
EXPLANATION: (d)
#QID# 43591
(44.) When phenol is treated with excess of bromine water, it gives
(a.) m-bromophenol
(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?
ANSWER: a
#QID# 43654
(46.)
Product is
(a.)
(b.)
(c.)
(d.)
ANSWER: c
#QID# 43505
(47.) In the reaction,
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)
#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)
#QID# 43717
(49.) What is formed when glycerol reacts with excess of HI?
(a.)
(b.)
(c.)
(d.)
ANSWER: c
EXPLANATION: (c)
#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
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
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)
ANSWER: a
#QID# 43757
(54.) Which of the following combinations can be used to synthesise ethanol?
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
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
ANSWER: c
EXPLANATION: (c)
In presence of HNO3 or alkaline KMnO4
#QID# 43511
(58.) In the reaction,
Oxidation NH3
CH3 OH→ A→ B; A and B are
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
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
(c.) Chlorine
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
(b.) Pentene
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)
#QID# 43637
(64.) At 530 K, glycerol reacts with oxalic acid to produce
(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.)
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
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)
#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
(d.) Propanal
ANSWER: c
#QID# 43517
(69.) Propan-1-ol can be prepared from propane by
ANSWER: c
EXPLANATION: (c)
#QID# 43663
(70.) In Lucas test an alcohol reacts immediately and gives insoluble chloride.
The alcohol is
(a.) CH3 OH
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)
#QID# 43540
(72.) Anisole can be prepared by the action of methyl iodide on sodium phenate.
The reaction is called
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
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
(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
ANSWER: d
EXPLANATION: (d)
#QID# 43706
(76.)
The product 𝐴 is
(a.)
(b.)
(c.)
(d.)
ANSWER: d
EXPLANATION: (d)
(a.) Acetone
(b.) Ethanol
(c.) Glycerol
(d.) Glycol
ANSWER: c
EXPLANATION: (c)
#QID# 43514
(78.) 𝑅CH2 CH2 OH can be converted to 𝑅CH2 CH2 COOH by the following
sequence of steps
(c.) KCN, H3 O+
#QID# 43560
(79.) In the reaction,
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
(c.) 2, 3-dimethyl-2-propanone
ANSWER: b
EXPLANATION: (b)
#QID# 43497
(81.)
The product is
(a.)
(b.)
(c.)
(d.)
ANSWER: a
EXPLANATION: (a)
#QID# 43580
(82.) CH3 CH3
| |
Conc.H2 SO4
In the reaction Ph − C − C − Ph → 𝐴 The product 𝐴 is
| |
OH OH
(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.)
#QID# 43749
(i)CH3 MgCl
(84.) → 𝑋
(ii)H2 O
The product obtained in this reaction is
ANSWER: c
#QID# 43703
(85.) A fruity smell is obtained by the reaction of ethanol with
(b.) PCI5
ANSWER: c
EXPLANATION: (c)
#QID# 43557
(86.) Hydroboration oxidation of 4-methyl octene would give
(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
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
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
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,
(a.) NaBH4
(b.) LiAlH4
ANSWER: a
#QID# 43660
NaNO2 /H2 SO4 H2 O NaOH
(92.) Phenol→ 𝐵→ 𝐶→ 𝐷
Name of the reaction is
ANSWER: a
EXPLANATION: (a)
#QID# 43683
(93.) Alcoholic beverages contain
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 +
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
(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
(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)
#QID# 43617
(99.) Cyclohexanol on reaction with 𝑃𝐵𝑟3 in presence of pyridine gives
(a.) Bromocyclohexane
(b.) Bromocyclohexane
(c.) 1-bromocyclohexanol
ANSWER: a
EXPLANATION: (a)
#QID# 43680
(100.) Correct acidic order of the following compounds is
ANSWER: b
EXPLANATION: (b)
(a.)
(b.)
(c.)
(d.)
ANSWER: d
#QID# 43755
(102.) To prepare an ether by Williamson’s synthesis, the reactants needed are
ANSWER: c
EXPLANATION: (c)
#QID# 43732
(103.) In the reaction,
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
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
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
ANSWER: a
#QID# 43563
(107.) The reaction,
Is called
ANSWER: a
EXPLANATION: (a)
#QID# 43506
(108.) Alcohols cannot be prepared from
(c.) O
||
Na/EtOH
CH3 − C − OCH3 →
H2 O
(d.) CH3 CH2 Cl →
ANSWER: d
EXPLANATION: (d)
#QID# 43583
(109.) Which of the following reagents may be used to distinguish between
phenol and benzoic acid?
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
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
ANSWER: b
EXPLANATION: (b)
#QID# 43689
(112.) The correct order of decreasing acidity of nitrophenols will be
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
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.
ANSWER: a
#QID# 43500
(115.) The enzymes which are used to convert starch into ethyl alcohol are
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
(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)
#QID# 43649
(119.) Which is not correct?
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
(b.) Anhydride
(c.) Acid
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
(d.) 2, 4, 6-tribromophenol
ANSWER: d
#QID# 43626
(122.) Which of the following reaction is/are feasible?
(a.)
(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
ANSWER: d
EXPLANATION: (d)
ANSWER: c
#QID# 43543
Reaction
(126.) Chlorobenzene → Phonel
𝑌
Salicyladehyde X and Y reactions are respectively……….
ANSWER: c
EXPLANATION: (c)
#QID# 43712
(127.) Identify the product/s in the following reaction.
𝐵𝐻3 H2 O2 /OH−
3CH3 CH = CH2 → 𝑋 → Products +H3 BO3
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
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.)
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
ANSWER: c
EXPLANATION: (c)
#QID# 43672
(132.) When phenolic ether is heated with HI, it yields
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
ANSWER: b
#QID# 43629
𝑃/𝐼2 𝐴𝑔𝑁𝑂2 𝐻𝑁𝑂2 NaOH
(134.) 𝐼𝑠𝑜-butyl alcohol → → → → 𝐴
True statement about 𝐴 is
ANSWER: a
EXPLANATION: (a)
#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
ANSWER: c
#QID# 43598
Jones
(138.) CH3 CH = CH − CH − CH3 → ? product is
reagent
|
OH
ANSWER: b
EXPLANATION: (b)
#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
ANSWER: b
EXPLANATION: (b)
#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?
(b.) Ethylene
(c.) Acetylene
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
ANSWER: c
EXPLANATION: (c)
#QID# 43575
(143.) When ethyl alcohol is heated with conc.H2 SO4 , the product obtained is
(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
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+
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
(c.) HBr
ANSWER: b
EXPLANATION: (b)
#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
(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
ANSWER: a
EXPLANATION: (a)
(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)
#QID# 43529
(151.) By heating phenol with chloroform in alkali, it is converted into
(b.) Salicyladehyde
(c.) Anisole
EXPLANATION: (b)
#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)
#QID# 43509
(153.) Which of the following represents the Dow process for the manufacture of
phenol?
(a.)
(b.)
(c.)
ANSWER: a
EXPLANATION: (a)
(a.)
(b.)
(c.)
ANSWER: c
EXPLANATION: (c)
(a.) Propane-1-ol
(b.) 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
(b.) C2 H5 OH
(c.) CH3 OH
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
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.)
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
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
ANSWER: b
#QID# 43695
𝑋
(162.) Phenol → forms a tribromo derivative “X ” is
ANSWER: b
#QID# 43718
(163.) Which of the following reagent will convert glycerol to acrolein?
(a.) P2 O5
(c.) KHSO4
#QID# 43761
(164.) Ether on reacting with P2 S5 form
(b.) Thioalcohol
(c.) Thioether
(d.) Thioaldehyde
ANSWER: c
EXPLANATION: (c)
#QID# 43618
(165.) When benzene sulphonic acid and p-nitrophenol are treated with NaHCO3 ,
the gases released respectively are
(b.) SO2 , NO
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
ANSWER: c
#QID# 43512
(167.) Phenol is soluble in water because
ANSWER: a
#QID# 43535
(168.) 1-propanol and 2-propanol can be distinguished by
EXPLANATION: (c)
#QID# 43501
(169.) The compound on dehydrogenation gives a ketone. The original compound
is
ANSWER: b
EXPLANATION: (b)
#QID# 43521
(170.) Formation of diethyl ether form ethanol is based on a
ANSWER: a
EXPLANATION: (a)
#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)
#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
(d.) 2, 4, 6-tribromophenol
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
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
(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
ANSWER: b
EXPLANATION: (b)
#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
ANSWER: d
EXPLANATION: (d)
ANSWER: a
EXPLANATION: (a)
#QID# 43518
(182.) Salicyl aldehyde is obtained when phenol is heated with CHCl3 and
aqueous NaOH. This reaction is known by which name?
ANSWER: c
EXPLANATION: (c)
#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)
#QID# 43584
(184.) Primary, secondary and tetiary alcohols are distinguished from one another
by
ANSWER: c
EXPLANATION: (c)
#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
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
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
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)
#QID# 43601
(190.) Ethyl chloride is converted into diethyl ether by
ANSWER: d
EXPLANATION: (d)
#QID# 43644
(191.) Which of the following will not react with NaOH?
(a.)
(b.) C2 H5 OH
(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
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
ANSWER: a
EXPLANATION: (a)
(a.)
(b.)
(c.)
ANSWER: d
EXPLANATION: (d)
(a.) C2 H5 OH
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
ANSWER: a
EXPLANATION: (a)
#QID# 43750
(197.) Among the following compounds which can be dehydrated very easily?
(b.) OH
|
CH3 CH2 CH2 CHCH3
(c.) CH3
|
CH3 CH2 CCH2 CH3
|
OH
ANSWER: c
EXPLANATION: (c)
#QID# 43558
(198.) Phenol gives characteristic colouration with
ANSWER: c
EXPLANATION: (c)
#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.)
ANSWER: d
#QID# 43525
(201.) The reaction,
C2 H5 ONa + C2 H5 I → C2 H5 OC2 H5 + NaI is known as
ANSWER: c
EXPLANATION: (c)
#QID# 43502
(202.) Choose the incorrect statement
(b.) The alcohol sold in the market for polishing etc, is known as methylated
spirit
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?
(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
(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)
#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?
(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
(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
(b.) CH3 − O − C2 H5
(c.) C2 H5 − O − C2 H5
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
(b.) Glucose
(c.) Fructose
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
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
(d.) Fluorescein
ANSWER: a
EXPLANATION: (a)
#QID# 43711
(214.) Which substance will not react with ϕ NNCl (ϕ = Phenyl) to give dye?
(a.)
(b.)
(c.)
(d.)
ANSWER: d
EXPLANATION: (d)
#QID# 43499
(215.) CH3 CH2 OH convert into CH3 CHO in the presence of
(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
ANSWER: c
EXPLANATION: (c)
#QID# 43671
(217.) The reaction of 𝑛𝑒𝑜-pentyl alcohol with concentrated HCl gives
(b.) 2-chloro-2-methylbutane
(c.) 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
(d.) Alcohols
ANSWER: d
EXPLANATION: (d)
#QID# 43754
(220.) Order of reactivity of halogen acids towards an alcohol is
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?
ANSWER: c
EXPLANATION: (c)
#QID# 43519
(222.) In Williamson’s synthesis ethoxy ethane is prepared by
(a.) Passing ethanol over heated alumina
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
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
ANSWER: c
EXPLANATION: (c)
#QID# 43705
(225.) In which case, methyl t-butyl ether is formed?
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,
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)
#QID# 43665
(228.) Which doesn’t form in the acid catalysed rearrangement of cumene
hydroperoxide?
(a.)
(b.)
(c.)
(d.)
ANSWER: d
EXPLANATION: (d)
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
(b.)
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)
#QID# 43547
(234.) When phenyl magnesium bromide reacts with t-butanol, the product would
be
(a.) Benzene
(b.) Phenol
ANSWER: a
EXPLANATION: (a)
#QID# 43504
(235.) Which one of the following gases is liberated when ethyl alcohol is heated
with methyl magnesium iodide?
(a.) Methane
(b.) Ethane
(d.) Propane
ANSWER: a
EXPLANATION: (a)
#QID# 43716
(236.) Which of the following is the best method for making 𝑖𝑠𝑜-propylmethyl
ether?
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
ANSWER: d
EXPLANATION: (d)
#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
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
(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)
#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 →
ANSWER: b
#QID# 43544
(246.) Which of the following is dihydric alcohol?
(a.) Glycerol
(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
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
(b.)
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)
#QID# 43733
(250.) Carbolic acid is
(a.) HCOOH
(d.) C6 H5 OH
ANSWER: d
EXPLANATION: (d)
#QID# 43607
(251.) An organic compound C3 H6 O neither gives precipitate with semicarbazide
nor reacts with sodium. It could be
ANSWER: d
EXPLANATION: (d)
(a.)
(b.)
(c.)
(d.)
ANSWER: a
#QID# 43756
(253.) The correct order of the solubility of different alcohols in water is
EXPLANATION: (a)
#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
ANSWER: c
#QID# 43670
(256.) Strength of acidity is in order
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
ANSWER: d
EXPLANATION: (d)
#QID# 43550
(258.) The order of reactivity of the following alcohols
(a.) I > 𝐼𝐼 > 𝐼𝐼𝐼 > 𝐼𝑉
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
#QID# 43570
(260.) Phenol, 𝑝-methylphenol, 𝑚-nitrophenol and 𝑝-nitrophenol follows order
of increasing strength as
ANSWER: b
EXPLANATION: (b)
#QID# 43530
(261.) The density of glycerol is higher than propanol due to
EXPLANATION: (b)
#QID# 43613
(262.) When phenol is heated with phthalic anhydride and H2 SO4 , it produces
(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
ANSWER: d
EXPLANATION: (d)
Cold HI
C6 H5 O − 𝑅 → C6 H5 OH + 𝑅I
Aryl-alkyl ether phenol alkyl
iodide