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Lakshya JEE 2.0 2024

Alcohol, Phenol & Ether DPP-01

1. Match the columns - 3. Mechanism of acid catalysed hydration reaction

Column-I Column-II involves -
A. OH P. Quinol (a) Protonation of alkene to form carbocation by
electrophilic attack of H3O+.
(b) Nucleophilic attack of water on carbocation.
(c) Deprotonation to form alcohol.
B. OH Q. Phenol (1) (a) and (b) (2) (a) and (c)
OH
(3) (a), (b) and (c) (4) (b) and (c)
4. Read the following statements and choose the correct
C. OH R. Catechol option-
(a) Ethanol on dehydration at 443K gives ethene.
(b) Ethanol on dehydration at 413K gives diethyl
OH
OH ether.
D. S. Resorcinol
(c) The dehydration of 2º and 3º alcohols to give
corresponding ethers is unsuccessful as
elimination competes over substitution.
(d) 1º alcohol > 2º alcohol > 3º alcohol ( Ease of
OH dehydration)
2. Match the columns - (1) TTFF (2) TFTF
Column-I Column-II (3) TTTF (4) FTTF
A. P. No-reaction
O 5. Which of the following statements are correct
 regarding dehydration of alcohols.
⎯⎯⎯
H 3O
→ I. Conc. H2SO4 or Con. H3PO4 or An. ZnCl2 or
B. CH3 Q. CH3 Al2O3 can be used as dehydrating alcohol.
| |
CH3 − C − O − CH − CH3 CH3 − C − OH II. The mechanism involves : Protonation →
| | | Formation of carbocation → Deprotonation
CH3 CH3 CH3 III. Primary alcohols are easiest to dehydrate.
 IV. Formation of carbocation is rds step.
⎯⎯⎯
H 3O
→ is one of
the product (1) I, II, III (2) II and IV
(3) I, II, IV (4) I, II, III and IV

C. CH3 R. OH 6. Which of the following statements are correct?

O C CH3 (a) In phenols, the —OH group is attached to sp2
CH3

hybridised carbon of an aromatic ring.
⎯⎯⎯
H 3O
→ is one of the (b) The carbon – oxygen bond length (136 pm) in
product of the phenol is slightly more than that in methanol.
reaction (c) Partial double bond character in C–O bond of
D. CH3 S. CH3 − CH − OH phenol is due to the conjugation of unshared
O CH |
CH3 CH3 electron pair of oxygen with the aromatic ring.
H 3O  (d) –OH group in phenol show +M-effect.
⎯⎯⎯→ is one of the
(1) (a), (b) and (v) (2) (a), (b) and (c)
product of the
reaction (3) (a), (c) and (d) (4) (a) and (d)
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7. Which of the following reactions will yield phenol? 11. An alcohol (A) on treatment with conc. H2SO4 gave
Cl an alkene (B). The compound (B), on reacting with
Br2 water and subsequent dehydrobromination with
(a) ⎯⎯⎯⎯⎯⎯⎯⎯⎯
(i)fusion with NaOH at 300 atm
⎯→ NaNH2 produced a compound (C). The compound
+
(ii)H 2O/H (C) with dil. H2SO4 in presence of HgSO4 gave a
NH2 compound 'D'. The compound D can also be obtained
by oxidation of A by acidified KMnO4 or from dry
heating of calcium acetate. Calculate molecular
(b) ⎯⎯⎯⎯⎯⎯→
(i)NaNO2 /HCl
(ii)H O(Warming) weight of 'C'.
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12. Complete the following reactions by writing

(c) ⎯⎯⎯⎯⎯⎯⎯(i)Oleum
(ii) NaOH,( Heating )
→ appropriate reactant or major product.
(iii)H + H2SO4
Cl ‘A’
4 13 K
(a) CH3CH2OH
(i)NaOH( aq.)298K/1atm
(d) ⎯⎯⎯⎯⎯⎯⎯⎯ → H2SO4
(ii)HCl ‘B’
4 43 K
(1) (a), (b) and (c) (2) (a) and (c) CH3
(3) (a), (c) and (d) (4) (b), (c) and (d) (b) CH3–Cl + CH3–C–ONa
8. Which of the following would not produce phenol as
final product -
CH3
CH3
(1) Acidification of sodium benzene sulphonate.
(2) Hydrolysis of benzene diazonium chloride. (c) CH3–C–Cl + CH3 –ONa
(3) Oxidation of toluene by hot alkaline KMnO4.
CH3
(4) Dow process.
OCH3
9. Statement-I : With HI, anisole gives methyl phenyl
oxonium ion is formed as intermediate.
Statement-II : The attack of I– on methyl phenyl (d) A + B ⎯⎯
→ + NaX
( Alkyl halide )
oxonium ion produces methanol and phenyl iodide.
(1) Statement-I is correct, statement-II is also correct. OH
(2) Statement-I is correct, statement-II is
incorrect. (e) ⎯⎯⎯
NaOH
→ A ⎯⎯⎯
CH3Cl
→B
(3) Statement-I is incorrect, statement-II is correct.
(4) Both statements-I and II are incorrect. (f) CH3 − O − CH3 ⎯⎯⎯
HBr
→ A ⎯⎯⎯
HBr
→B
alcohol
10. At 413 K, ethanol is dehydrated to produce
ethoxyethane. (g) CH3 − O − CH2 − CH3 ⎯⎯
HI
→
CH3 − CH2 − OH ⎯⎯⎯→
H2SO4
C2H5OC2H5 CH3
413K HI
Read the statements given below, and choose the (h) CH3–O–C–CH3
option containing correct statements. CH3
I. Such reaction is suitable for preparation of OCH3
ethers having primary alkyl groups only.
II. The mechanism involves following sequence-
Protonation of alcohol → Attack of another (i) ⎯⎯⎯
HBr
→
alcohol molecule on protonated alcohol →
OCH3
Deprotonation
III. At 443K, the same reaction would produce
ethene as major product. (j) ⎯⎯⎯⎯⎯ Br2
Ethanoic Acid
→
(1) I, II (2) II, III
(3) I, III (4) I, II, and III
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Note: Kindly find the Video Solution of DPPs Questions in the DPPs Section.
Answer Key
1. (A-Q) ; (B-R) ; (C-S) ; (D-P)
2. (A-P) ; (B-Q, S) ; (C-P, Q) ; (D-R, S)
3. (3)
4. (3)
5. (3)
6. (3)
7. (1)
8. (1,3)
9. (2)
10. (4)
11. (40)
CH3
12. (a) A  CH3–CH2–O–CH2–CH3 (b) CH3–C–O–CH3
B  CH2=CH2 CH3
CH2
(c) (d) A  CH3–X X  Cl, Br, I
CH3–C–CH3 ONa
B

ONa OCH3

(e) A  B (f) A  CH3–OH

B  CH3–Br
CH3
(g) CH3 − I + CH3 − CH2 − OH (h) CH3–OH + CH3–C– I
CH3
OH OCH3 OCH3
Br
(i) + CH3Br (j)

Br Minor
Major

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