Alcohols

ALCOHOLS, PHENOLS AND ETHERS
Q.1 Kolbe’s reaction involves the conversion of

(a) Phenol to benzoic acid (b) Phenol to benzaldehyde
(c) Phenol to benzoquinone (d) Phenol to o – hydroxybenzoic
acid
Ans. (d)
Q.2 HCHO on reaction with CH3MgBr followed by hydrolysis gives
(a) CH3OH (b) CH3OCH3 (c) CH3CH2OH (d)
CH3CHO
Ans. (c)
Q.3 Which among the following show tautomerism?
(a) Alcohols (b) Phenol (c) Ethers (d)
Anisole
Ans. (b)
Q.4 Which one of the following is inter – molecular dehydration?
(a) ROH ® R – OR (b) ROH ® R – X
(c) ROH ® Alkene (d) R – X ® R – OH
Ans. (a)
Q.5 Cumene O2, H2O/ H+ X and Y
X and Y respectively are
(a)Toluene, propene (b) Toluene, propylchloride
(c) Phenol, acetone (d) Phenol, acetaldehyde
Ans. (c)
Q.6 How many minimum number of carbons are needed for an optically active
ether?
(a) 2 (b) 3 (c) 4 (d) 5
Ans. (b)
Q.7 Order of nucleophilicity is
(a) CH3O- < C2H5O- (b) C2H5O- < C2H5S-
(c) CH3O- < C2H5S- (d) All of these
Ans. (d)
Q.8 Oxidation of phenol with chromic acid gives
(a) Benzaldehyde (b) Benzoic acid
(c) p – Benzoquinone (d) Acetophenone
Ans. (c)
Q.9 Among the following four compounds
(i) Phenol, (ii) Methyl phenol, (iii) Meta nitrophenol, (iv) Para nitrophenol
The acidity order is
(a)(iv) > (iii) > (i) > (ii) (b) (iii) > (iv) > (i) > (ii)
(c) (i) > (iv) > (iii) > (ii) (d) (ii) > (i) > (iii) > (iv)
Ans. (a)
Q.10 Which one of the following will not form a yellow precipitate on heating
with an alkaline solution of iodine?
(a) CH3CH(OH)CH3 (b) CH3CH2CH(OH)CH3
(c) CH3OH (d) CH3CH2OH
Ans. (c)
In the following questions, a statement of assertion followed by a statement of

reason is given. Choose the correct answer out of the following choices.
(a)Assertion and reason both are correct statements and reason is correct
explanation for assertion.
(b)Assertion and reason both are correct statements but reason is not correct
explanation for assertion.
(c)Assertion is correct statement but reason is wrong statement.
(d)Assertion is wrong statement but reason is correct statement.
(e) Both Assertion and reason are wrong statements.
Q.11 Assertion: In esterification reaction, HCOOH is the most reactive acid
among carboxylic acid.
Reason: Alcohol acts as nucleophile.
Ans. (b)
Q.12 Assertion: Phenol does not react with NaHCO3.
Reason: Phenol is less acidic than H2CO3.
Ans. (a)
Q.13 Assertion: When 3,3 – dimethylbutane – 2 – ol is heated in presence of
concentrated H2SO4 then 2,3 – dimethylbut – 2 – ene is formed as major
product.
Reason: In this recation, carbocation is formed as an intermediate and shifting
of CH3- take place.
Ans. (a)
Q.14 Assertion: The reactivity order of alcohols is 1o > 2o > 3o for the reaction
in which
O – H bond is broken.
Reason: The reactivity order of alcohol is 3o > 2o > 1o for the reaction in which
C – O bond is broken.
Ans. (b)
Q.15 Assertion: Among all ortho halophenol, fluorophenol is least acidic.
Reason: Ortho – fluorophenol forms intramolecular H – bond.
Ans. (a)
Q.16 Assertion: (CH3)3 C – CH = CH2 on hydroboration oxidation gives
(CH3)3 C –CH2CH2 – OH as major product.
Reason: It involves the formation of carbocation.
Ans. (c)
Q.17 Assertion: The dehydration of ethyl alcohol with Al2O3 at 633 K gives
ethene.
Reason: The reaction proceeds through the formation of carbocation
intermediate.
Ans. (c)
Q.18 Assertion: Ortho and para nitrophenols are more acidic than phenol.
Reason: Phenoxide ion formed by ortho and para nitrophenols are more stable
than phenoxide ion formed by phenol.
Ans. (a)
Q.19 Assertion: Phenols give o- and p- nitrophenol on nitration with conc.
HNO3 and H2SO4 mixture.
Reason: - OH group in phenol is o-, p- directing.
Ans. (a)
Q.20 Assertion: The bond angle in ethers is slightly less than the angle of
tetrahedral.
Reason: There is repulsion between the two bulky (- R) groups.
Ans. (d)
Q.21 Ortho-nitrophenol is more acidic than ortho-methoxyphenol. Why?
Q.22 Diethyl ether does not react with sodium. Why?
Q.23 Phenols do not undergo substitution of the –OH group like alcohols. Why?
Q.24 Give a chemical test to distinguish between the given pairs –

(a)Phenol and cyclohexanol (b) Propan-2-ol and Benzyl alcohol
Q.25 Alcohols react both as nucleophiles as well as electrophiles. Write one

reaction of each type and describe its mechanism.
Q.26 Write the main products in each of the following reactions –

(a) (CH3)3C-O-CH3 + HI ® ?
(b) CH3-CH=CH2 + B2H6, 3H2O2/OH- ® ?
(c) C6H5-OH + aq.NaOH + CO2 + H+ ® ?
Q.27 Do the following conversions –

(a) Phenol to anisole (b) Propan-2-ol to 2-methylpropan-2-ol
(b) Aniline to phenol (d) 2-Methylpropanol to 2-Methylpropene
(e)Phenol to benzoquinone
Q.28 Among HI, HBr, HCl, HF, which is the most reactive towards alcohols.
Why?
Q.29 What happens when

(a) Phenol reacts with bromine water?
(b)Ethanol reacts with CH3COCl/ pyridine?
(c)Anisole reacts with HI?
Q.30 Distinguish between – (a) Ethanol and phenol

(b) Propan-2-ol and 2-methylpropan-2-ol.
Q.31 Write the products in each of the following reactions –

(a) C6H5-O-CH3 + HI ® ?
(b)(CH3)3C-OH + Cu/ 573K ® ?
(c)C6H5-OH + Zn dust ® ?
Q.32 What do you mean by Williamson’s synthesis? What is its limitation?
Q.33 Explain the mechanism of the following reactions-

(a) Addition of Grignard’s reagent to the carbonyl group of a compound
forming an adduct followed by hydrolysis.
(b) Acid catalyzed dehydration of an alcohol forming an alkene.
(c) Acid catalyzed hydration of an alkene forming an alcohol.
Q.34 The following is not an appropriate reaction for the preparation of tert.-
butyl ethyl ether: C2H5ONa + (CH3)3C-Cl (CH3)3C-OC2H5
(a) What would be the major product of the given reaction?

(b) Write a suitable reaction for the preparation of tert.-butyl ethyl ether,
specifying the names of reagents used. Justify your answer in both cases.
Q.35 An aromatic compound ‘A’ having molecular formula C3H6 on treatment

with aqueous H2SO4 gives ‘B’ which on treatment with HCl/ZnCl2 gives ‘C’.
The compound ‘C’ on treatment with ethanolic KOH gives back the compound
‘A’. Identify the compounds A, B, C.
NOTE: Do all NCERT questions compulsorily.

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ALCOHOLS, PHENOLS AND ETHERS

Q.1 Kolbe’s reaction involves the conversion of

In the following questions, a statement of assertion followed by a statement of

Q.21 Ortho-nitrophenol is more acidic than ortho-methoxyphenol. Why?

Q.22 Diethyl ether does not react with sodium. Why?

Q.24 Give a chemical test to distinguish between the given pairs –

Q.25 Alcohols react both as nucleophiles as well as electrophiles. Write one

Q.26 Write the main products in each of the following reactions –

Q.27 Do the following conversions –

Q.29 What happens when

Q.30 Distinguish between – (a) Ethanol and phenol

Q.31 Write the products in each of the following reactions –

Q.32 What do you mean by Williamson’s synthesis? What is its limitation?

Q.33 Explain the mechanism of the following reactions-

(a) What would be the major product of the given reaction?

Q.35 An aromatic compound ‘A’ having molecular formula C3H6 on treatment

NOTE: Do all NCERT questions compulsorily.

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