Yes

Chapter 11
Alcohols, Phenols and Ethers
Solutions
SECTION - A
Objective Type Questions
(Classification and Nomenclature of Alcohols, Phenols and Ethers)
1. Which among the following is alcohol?
OH O OH OH
(1) (2) HO (3) (4)

H
O CN
Sol. Answer (2)
HO has only –OH as functional group.
2. Which one is ether?
O
(1) (2) O—R (3) CH3CH — CH2 (4) All of these
O
Sol. Answer (4)
R – O – R is ether.
3. Which one is phenol?
NO2 O OH
(1) OH (2) H C OH (3) CH2 OH (4) CN
Sol. Answer (1)
OH
NO 2
m-nitrophenol
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146 Alcohols, Phenols and Ethers Solutions of Assignment (Set-2)
4. IUPAC name of HOCH2CH2 OH is

(1) Ethylene glycol (2) Ethane-1,2-diol (3) Ethyl-1,2-diol (4) Ethylene diol
Sol. Answer (2)
1 OH
2 OH
Ethane –1, 2–diol
O
5. IUPAC name of is
(1) Ethyl propyl ether (2) Propyl elhoxide (3) Ethoxy propane (4) Propoxy ethane
Sol. Answer (3)
O
Ethoxy propane
OC2H5
6. IUPAC name of is
(1) Benzyl ethoxide (2) Ethoxy benzyl

(3) Benzene ethoxide (4) Ethoxy benzene
Sol. Answer (4)
OEt
(Ethoxy benzene)
(Preparation of Alcohols and Phenols)

7. 3° alkyl halides form alcohols preferably via
(1) SN2 (2) SN1 (3) Transition state (4) SNi
Sol. Answer (2)
3° alkyl halides
SN1
Cl +
(Carbocation)
Stable
8. Which one is preferable reagent for given reaction?
R CH2 — X  HO — CH2 R
(1) (H2O + KOH) (2) (ROH + KOH) (3) (ROH + KOH) /  (4) (H2O + KOH) / 
Solutions of Assignment (Set-2) Alcohols, Phenols and Ethers 147
Sol. Answer (1)
R — CH2 — X  HO — CH2 — R
The reagent used must be H2O + KOH.
9. SN1 mechanism is observed in
R aq. KOH
(1) CH X (2) R — OH + SOCl2
R
alc. KOH
(3) R – X (4) ROH + HX
Sol. Answer (1)
R
aq. KOH
CH X SN1
R
aq KOH
10. CH2— Cl CH2 — OH
Reaction happens via

(1) SN1 (2) SN2 (3) SNi (4) ArSN1
Sol. Answer (1)
aq KOH
CH2— Cl SN1
CH2OH
+
H /H2O
11. CH3CH CH2 major product is
OH
(1) CH3 – CH – CH2 (2) CH3CHCH3 (3) CH3CH2CH2OH (4) CH 3CH — CH2
O OH OH
Sol. Answer (2)
+
+
+ H + H2O
OH
12. Grignard reagent is suitable reagent for the preparation of which of the following, from carbonyl compound?
(1) 1° alcohols (2) 2° alcohols (3) 3° alcohols (4) All of these
Sol. Answer (4)
13. HCHO + A CH2 — OH

A is
(1) Mg — X (2) CH3 (3) OH (4) OCH3
Sol. Answer (1)
R [?] R
14. C O CH — OH
R R
Here reagent is
(1) LiAlH4 (2) NaBH4 (3) Ni/H2 (4) All of these
Sol. Answer (4)
R
LiAlH4
O R2CHOH
R NaBH4
Ni, H2
R2CHOH
R2CHOH
O
[?]
15. R C — OH R CH2 — OH
Here reagent is
(1) LiAlH4 (2) NaBH4 (3) Both (1) & (2) (4) Red P/HI
Sol. Answer (1)
O
LiAlH4
R C — OH R CH2 — OH
16. Lucas test is used to distinguish

(1) Phenols (2) Ethers (3) Alcohols (4) Alkyl halides
Sol. Answer (3)
Alcohols are distinguished by Lucas reagent test.
17. In Lucas test immediate turbidity is caused by

(1) 3° alcohols (2) 2° alcohols (3) 1° alcohols (4) Phenol
Sol. Answer (1)
3° Alcohols gives sudden turbidity.
(Physical and Chemical properties of Alcohols and Phenols)
18. Which among the following show tautomerism?
(1) Alcohols (2) Phenol (3) Ethers (4) Anisole
Sol. Answer (2)
OH O
Enol form Ketoform
19. Which one will be optically active?
H
OH
(1) OH (2) OH (3) OH (4)
H
Sol. Answer (1)
*
OH
This molecule has a chiral centre.
∵ Optically active.
20. ROH + SOCl2 ?

The final product is
(1) Alkyl chloride (2) Alkyl sulphate (3) Alkene (4) Ether
Sol. Answer (1)
ROH + SOCl2 R — Cl
Alkyl chloride
(1) O LiAlH
21. RCH  CH2  3
(2) H O/ Zn
(A) 
4
(B)
2
Product (B) is
(1) RCHO + HCHO (2) RCHO + HCOOH (3) RCOOH + HCOOH (4) RCH2OH + CH3OH
Sol. Answer (4)
O3 R — CHO + H CHO
R
H2O/Zn
LiAlH4
R — CH2OH + CH3OH
22. Reaction involving cyclic intermediate and anti addition is

+
H /H2O HX
(1) CH2 CH2 (2) CH3CH CH2
Hg(OAc)2/H2O B2H6/ THF

(3) CH3CH CH2 NaBH4
(4) CH2 CH2 –
H2O2/OH
Sol. Answer (3)

Hg(OAC)2/H2O
CH3CH CH2
NaBH4
This is oxymercuration-demercuration, reaction and involves anti-addition.
23. Boiling point will be least for
(1) OH (2) (3) (4)

O
OH
Sol. Answer (2)
This having least boiling point.
24. Which one is most viscous?

OH
OH
(1) OH (2) (3) OH OH (4) OH
OH
Sol. Answer (3)
OH
OH OH
This is most viscous because of maximum hydrogen bonding.
25. Lowest boiling point is for

(1) Butanol (2) Pentanol
(3) 2-methyl propane-2-ol (4) 2-methyl butane-2-ol
Sol. Answer (3)
OH
has lowest B.P.
HX
26. R — OH
ZnCl2
(1) R — X (2) Alkene (3) Both (1) & (2) (4) No product
Sol. Answer (1)
+ –
R — OH + HX R + Cl
R — Cl
27. 1° alcohols preferably undergo dehydration in presence of Al2O3

(1) E1 (2) E2 (3) SN1 (4) SN2
Sol. Answer (2)
1° substrate favours E2 reaction for dehydration.
28. Which one is inter-molecular dehydration?

(1) ROH R — OR (2) ROH R—X
(3) ROH alkene (4) R — X ROH
Sol. Answer (1)

R  O H  HO  R 
H O
R O R
2
O
18 +
29. R' — OH + R C — OH H ?
Products are
O O
18 18
(1) R — C — O R' + H2O (2) R' — C — OR' + H2 O
O O
18 18
(3) R' — C — OR + H2 O (4) R' — C — OR + H2O
Sol. Answer (1)
O O
18  18
R – O H + HO – C – R –H2O R – O – C – R
30. Phenols can be distinguished from alcohols by

(1) FeCl3 (neutral) (2) Fehling solution (3) Tollen’s reagent (4) 2,4-DNP
Sol. Answer (1)
3– +
6 OH + FeCl3 [Fe (OPh)6] + 3HCl + 3H
(Violet)
31. Most acidic among the following is

OH
OH OH OH
(1) (2) (3) (4)

NO2 CH3 NO2
Sol. Answer (4)
–
OH O
+
+ H
N N
O O O O
(Stabilished anion
because of –M and –I
effect of –NO2)
32. Correct acidic order of acidity is
OH OH OH OH OH OH OH
OH
CH3 CH3
(1) > > > (2) < < <
CH3 CH3
CH3 CH3
OH OH OH OH OH OH OH
OH
CH3 CH3
(3) < < < (4) > > >
CH3 CH3
CH3 CH3
Sol. Answer (1)
The correct acidic order is,
OH OH OH OH
CH3
> > >
CH3
CH3
OH X
33.
The reagent X required for above conversion is
(1) LiAlH4 (2) Zn (3) (4) NaBH4
Sol. Answer (2)
OH
Zn
Dust
34. Electrophile in Reimer-Tiemann reaction

(1) CHCl3 (2) : CH2 (3) : CCl2 (4) CO2
Sol. Answer (3)
In Reimer-Tiemann reaction.
The major product is ortho isomer intermediate is (:CCl2)
35. In Reimer-Tiemann reaction, the major product is

(1) Ortho isomer due to intra molecular H-bonding
(2) Meta isomer
(3) Para isomer due to symmetry
(4) None of these
Sol. Answer (1)
Reimer-Tiemann reaction :
OH O H Intra - ‘H’ bond

C OH
CHCl3 + NaOH C
343 K H
+
(o-hydroxy benzaldehyde)
Major product
CHO
Due to presence of Intra ‘H’ bond (p-iso)
(Minor product)
36. Molecule which does not oxidise using PCC
(1) OH (2) OH (3) OH (4) OH
Sol. Answer (1)
OH
Phenol cannot oxidised by PCC.
(i) O
37. Cumene 
2
  X and Y
(ii) H2O, H
X and Y respectively are

(1) Toluene, propene (2) Toluene, propylchloride
(3) Phenol, acetone (4) Phenol, acetaldehyde
Sol. Answer (3)
OOH OH
O
+
O2 H
+
(Ethers (Preparation and properties)
38. Alcohols and ethers are

(1) Position isomers (2) Functional isomers (3) Chain isomers (4) Metamers
Sol. Answer (2)
Alcohols and ethers are functional isomers.
39. How many minimum number of carbons are needed for an optically active ether?
(1) 2 (2) 3 (3) 4 (4) 5
Sol. Answer (2)
CH3 – CH – CH2
O
1, 2 epoxy propane is optically active ether.
40. Which one is optically active aromatic ether?
O O O
(1) (2) (3) (4) O
Et
H H
Sol. Answer (1)
O
*
Et
H
This presence of chiral centre makes the molecule optically active.
41. Order of nucleophilicity is

(1) CH3O– < C2H5O– (2) C2H5O– < C2H5S– (3) CH3O– < CH3S– (4) All of these
Sol. Answer (4)
CH3O– < C2H5O–
C2H5O– < C2H5S–
CH3O– < CH3S–
∵ All the given choices are correct.
OCH3
CH3Br/ FeBr3
42. ? major product is
OCH3 OCH3 OCH3 OCH3

CH3
(1) (2) (3) (4)
Br
Br CH3
Sol. Answer (4)
OCH3 OCH3
CH3Br/FeBr3
CH3
(p-Major)
43. Which one of the following is best Lewis base?
O
O
(1) (2)
(3) OH (4) OH
Sol. Answer (2)

O
This is best Lewis base among the given options.
+
44. H2O/H ?
O
Product/(s) will be
OH
(1) OH (2)
OH +
(3) OH OH (4) OH
+
Sol. Answer (1)
H2O
+
H +
O O
H
2 OH
HI/
45. CH3 – O – CH2CH3 A + B
Excess
Product A and B are
(1) CH3OH + CH3CH2I (2) CH3I + CH3CH2OH
(3) CH3I + CH3CH2I (4) CH3OH + CH3CH2OH
Sol. Answer (3)
O
+ HI
CH3I + OH
SECTION - B
Objective Type Questions
(Preparation of Alcohols and Phenols)
(i) B 2 H6 H 2SO4
1. CH3CH–CH=CH 2 – X Y
(ii) H 2O2 /OH 140°
CH 3
What is Y?
(1) CH3–CH–CH2–CH2–O–CH2–CH2–CH–CH3
CH3 CH3
(2) CH3–CH–CH=CH2
CH3
(3) CH3–CH–CH–O–CH–CH–CH3
CH3 CH3 CH3 CH3
CH3 CH3
(4) CH3–C–O–C–CH3
C2H5 C2H5
Sol. Answer (1)

(1) B2H6
(2) H2O2/OH
– OH
H2SO4, 140°
NaOH
2. + H 2SO4 (fuming) X 570-620K
Y
What is Y?
OH SO3H ONa
(1) (2) (3) (4)
Sol. Answer (3)

– +
SO3H O Na
NaOH
+ H2SO4
(Fuming) 570-620 K
Y
(1) Mg Br2
3. CH2 CH CH2 Br A B
(2) HCHO CCl4
+
(3) H3O KOH
C
Product (C) is
(1) (2) ..
O O
..
HO
CH 2 CH CH2 CH2 OH
(3) (4)
OH OH HO O
Sol. Answer (3)
Br
+ Mg MgBr
+
HCHO, H
CH2OH
+
(1) H , Br2, CCl4, KOH4
OH
OH
OH
4. Ethylene oxide when treated with Grignard reagent yields

(1) Primary alcohol (2) Secondary alcohol
(3) Tertiary alcohol (4) Cyclopropyl alcohol
Sol. Answer (1)
O
+ RMgX R OH
(1° alcohol)
O
Mg/ dry ether (I) CH 3–C–CH 3
5. Cl Br (1 mole)
A + B
(ii) H3O
What is B?
OH OH OH
(1) Cl C–CH3 (2) CH3–C C–CH3
CH3 CH3 CH3

OH
(3) CH3–C Br (4)
CH3
Sol. Answer (1)
OH
Clearly, B is Cl – .
∵ Br has more tendency to form RMgX, than 'Cl' because of more size. So, reaction will take place from
'Br' side. i.e.,
O
– +
C O Mg Br
Mg/dry ether (i). H3C CH3
Cl Br Cl MgBr Cl C CH3
(1 mole)
CH3
+
(ii). H3O
OH
Cl C CH3
CH3
H2SO 4 Sn + HCl NaNO 2 + HCl H2O

6. + HNO 3 X Y 0-5° C
Z A . What is A?
NH2 NO2 OH
(1) (2) (3) (4)
Sol. Answer (4)
NO2 NH2 OH
NaNO2, dil
H2SO4 Sn/HCl HCl H2O
+ HNO3 +
N2 Cl
–
(X) (A)
(Physical and Chemical properties of Alcohols and Phenols)
CH 2OH
7. + H2SO 4 A
170°C
(conc.)
What is the major product A?

CH2 CH3
CH3
(1) (2) (3) (4)
Sol. Answer (3)
OH
H
+
+ H
(Cyclohexene)
H

Br2/Fe
8. + CH3–CH2–CH2–OH  A B
What is the major product B?

CH2–CH2–CH3
(1) (2) CH 3–CH–CH 2
Br Br
CH3 CH3
CH3–C–Br CH3–CH
(3) (4)
Br
Sol. Answer (4)
–
1 – 2 H:
OH + Shift +
+ H +
Br2/Fe
Br
9. Which of the following is the correct increasing order of boiling point of following compounds?
CH3–CH2–CH2–OH CH3–CH–CH3 CH3–O–CH2–CH3
OH
I II III
(1) II < I < III (2) III < II < I (3) I < II < III (4) II < III < I
Sol. Answer (2)
The order of boiling point is
OH
OH O
> >
(I) (II) (III)
10. Which of the following is the correct ease of dehydration?
OH OH OH
CH3–CH2–CH2–CH2 CH3–CH2–CH–CH3 CH2=CH–CH–CH3
OH
III IV
I II
(1) I > III > II > IV (2) IV > III > II > I (3) IV > II > III > I (4) III > IV > II > I
Sol. Answer (2)
The ease of dehydration is,
OH
> > > OH
OH OH
(IV) (III) (II) (I)

H3O
A
11. CH3 – C = CH2 (1) B2H6 /THF
B
CH3 (2) H2O2 /OH
Product A and B can be distinguished by
(1) Sodium metal
(2) Neutral FeCl3
(3) Lucas reagent
(4) Esterification reaction
Sol. Answer (3)
OH
A (3°)
Lucas reagent can
distinguish them
B OH (1°)
CH3
Al2O3/ HBr
12. CH3 – C – OH A CH3–O–O–CH3
B
CH3 MgBr
aq. NaOH
D C
The end product D of the reaction is
O – C(CH3)3 (CH 3) 3 – C – CH 2
(1) (2)
OH
Br Br
(3) (4)
Br
Sol. Answer (3)
Br
A OH B
OH
C D
13. Consider the following reaction :

CH3 Cl Alkaline KMnO
Phenol 
Zn dust
X 
Anhydrous AlCl
 Y 
H O/H
4
Z
3 2
The product Z is
(1) Benzene (2) Toluene
(3) Benzaldehyde (4) Benzoic acid
Sol. Answer (4)
OH CH3 COOH
Zn CH3Cl Alkaline
AlCl3 KMNO4
(X) (Y) (Z)
OH OH OH
14. CH2–CH–CH2 + HI X
(excess)
What is X?
I I I I
(1) CH2–CH–CH2 (2) CH2=CH–CH2
(3) CH3–CH=CH2 (4) CH3–CH–CH3
Sol. Answer (4)
OH OH OH I
H2C CH CH2 + HI H3C CH CH3

(excess)
HI
I I I I I I
–I2 HI
H2C CH CH2 H2C CH CH2 H2C CH CH3
I
–I2
HI
H3C CH CH3 H2C CH CH3
Answer (4)
OH
red P Br2
15. + HI X h
Y
(1 eq.)
CH2OH
What is Y?
I OH OH
Br
(1) (2) (3) (4)
CH2Br CH2I CH2Br CH2Br

Sol. Answer (3)
OH OH OH
Red P Br2
+ HI
h
OH CH3 Br
16. Which of the following will not give positive test with neutral FeCl3?
(1) Nitrophenol (2) Phenol (3) Allyl alcohol (4) o-cresol
Sol. Answer (3)
OH
+ FeCl3 No Reaction
17. In Dow's process haloarene is converted to phenol with fused NaOH. The most reactive compound is
Cl Cl Cl
H H D D T T
(1) (2) (3) (4) All are equally reactive
H H D D T T
H D T
Sol. Answer (1)

Cl
H H
H H
H
18. Among the following four compounds

a. Phenol b. Methyl phenol c. Meta nitrophenol d. Para nitrophenol
The acidity order is
(1) d > c > a > b (2) c > d > a > b (3) a > d > c > b (4) b>a>c>d
Sol. Answer (1)
The acidic order is
Paranitrophenol > Meta-nitrophenol > Phenol > Methyl Phenol
H
CH3
C OH
SOCl2
19. Product (major)
Pyridine
The product is
Cl H
CH3 CH3
C H C Cl
(1) (2)
(3) Mixture of (1) & (2) (4) No reaction
Sol. Answer (1)

In presence of pyridene, the reaction of SOCl2 with alkyl halide is SNi (Intramolecular nucleophilic substitution
reaction) and hence SNi, the confuguration is retained.
i.e., retention reaction takes place in SNi. So,
H H
H3C
H3C C C Cl
OH
SOCl2
Pyridene
CH2
20. HCl aq KOH conc. H2SO4 . Product (C) is
1 eqv.
A B C (major)
CH3 CH2
(1) (2) (3) (4)
Sol. Answer (2)
CH2 CH2 – Cl CH2 – OH CH2
HCl aq.KOH Conc. H2SO4
leq.
.
(A) (B) (C)
(Ethers (Preparation and properties)
21. Reaction of t-butyl bromide with sodium methoxide produces

(1) Sodium t-butoxide (2) t-butyl methyl ether (3) Isobutane (4) Isobutylene
Sol. Answer (4)
– +
Br + CH3O Na
(Isobutylene)
O
CH3 CH3MgBr Cu
22. C CH2 + A 300ºC
B
CH3 H3O
B is
(1) (CH3)3CHO (2) CH3 – C = CH – CH3
CH3
(3) (CH3)2CHCOCH3 (4) CH3C – CH2 – CH2CH3
O
Sol. Answer (2)
O OH
CH3MgBr
+
H3O
Cu, 300°C
(B)
 In basic medium the opening of epoxide is SN2 type. So, nucleophile CH3 attack less hindered 'C' of
epoxide.
23. Ethyl chloride is converted into diethyl ether by

(1) Perkin’s reaction (2) Grignard reaction
(3) Wurtz synthesis (4) Williamson’s synthesis
Sol. Answer (4)
C2H5Cl o
This can be done by Williamson's synthesis.
CH3 CH CH2
PCl5 Mg O
24.  A ether B + C
H3O
O CH 2OH
Product (C) is
OH
(1) (2) (3) (4)
O O O O
OH O
OH
Sol. Answer (3)

PCl5
(A)
O CH2OH O Cl
Mg
(B)
O MgCl
o
(C)
O
OH
HI/ alc. KOH/ Cl2/h

25. excess A B C
O
Product C is
(1) Alkyl iodide (2) Vinyl chloride (3) Vinyl iodide (4) Allyl chloride
Sol. Answer (4)
Cl2
HI /  Alc. KOH/  Cl2/h
(A) (B) (Allyl chloride)
SECTION - C
Previous Years Questions
1. The compound A on treatment with Na gives B, and with PCl5 gives C. B and C react together to give diethyl
ether. A, B and C are in the order [NEET-2018]
(1) C2H5OH, C2H6, C2H5Cl
(2) C2H5OH, C2H5Cl, C2H5ONa
(3) C2H5OH, C2H5ONa, C2H5Cl
(4) C2H5Cl, C2H6, C2H5OH
Sol. Answer (3)
Na
C2H 5OH –
C 2H5O Na
+
(A) (B)
PCl 5
C2H5Cl
(C)
– + SN2
C2H5O Na + C2H5Cl C2H 5OC2H5
(B) (C)
So the correct option is (3)
2. In the reaction [NEET-2018]
– +
OH O Na
CHO
+ CHCl3 + NaOH
The electrophile involved is
(1) Dichloromethyl cation CHCl2  


(2) Formyl cation CHO  

(3) Dichlorocarbene : CCl2 
(4) Dichloromethyl anion CHCl2  


Sol. Answer (3)
It is Reimer-Tiemann reaction. The electrophile formed is :CCl2 (Dichlorocarbene) according to the following reaction
..
CHCl3  OH–

CCl3  H2 O
..
CCl3  : CCl2  Cl–
Electrophile
3. Identify the major products P, Q and R in the following sequence of reactions: [NEET-2018]
Anhydrous
AlCl3 (i) O2
+ CH3CH2CH2Cl P +
(ii) H3O /
Q+R
P Q R
CH2CH2CH3 CHO
(1) , , CH3CH2 – OH
CH2CH2CH3 CHO COOH
(2) , ,
OH
CH(CH3)2
(3) , , CH3 – CO – CH3
CH(CH 3)2 OH
(4) , , CH 3CH(OH)CH 3
Sol. Answer (3)

Cl
CH3CH2CH2 – Cl + Al
Cl Cl
+ 1, 2–H + –
Shift
CH3 – CH – CH3 CH3CH2CH2 Cl AlCl3
(Incipient carbocation)
Cl
–
AlCl3
Now,
CH3
CH – CH3
CH3 – CH – CH3 O2
(P)
CH3
OH HC
3 –C –O –O– H
O
+
H /H2O
CH3 – C – CH3 + Hydroperoxide
Rearrangement
(R) (Q)
4. Which one is the most acidic compound? [NEET-2017]
OH OH
(1) (2)
CH3
OH OH
O2N NO2
(3) (4)
NO2 NO2
Sol. Answer (4)
–NO2 group has very strong –I & –R effects.
5. The heating of phenyl-methyl ethers with HI produces. [NEET-2017]
(1) Ethyl chlorides (2) Iodobenzene
(3) Phenol (4) Benzene
Sol. Answer (3)
O – CH3 OH
HI
+ CH3I
6. The reaction,
NaH Me – I
OH O Na
Me
O
can be classified as [NEET-2016]
(1) Williamson alcohol synthesis reaction
(2) Williamson ether synthesis reaction
(3) Alcohol formation reaction
(4) Dehydration reaction
Sol. Answer (2)
Fact
7. Which of the following reagents would distinguish cis-cyclopenta-1, 2-diol from the trans-isomer?
[NEET-2016]
(1) Aluminium isopropoxide
(2) Acetone
(3) Ozone
(4) MnO2
Sol. Answer (2)
cis-cylopenta-1, 2-diol can form cyclic ketal whereas tran-cyclopenta-1, 2-diol can't form cyclic ketal.
OH O CH3
CH3
+O=C C
CH3
OH O CH3
8. Reaction of phenol with chloroform in presence of dilute sodium hydroxide finally introduces which one of the
following functional group? [Re-AIPMT-2015]
(1) –CHCl2 (2) –CHO
(3) –CH2Cl (4) –COOH
Sol. Answer (2)
OH OH
CHO
(i) CHCl3 + NaOH
(ii) H+
9. Which of the following is not the product of dehydration of OH ? [Re-AIPMT-2015]
(1) (2)
(3) (4)
Sol. Answer (4)

More stable carbocation can't be rearranged to a less stable carbocation.
10. Which of the following reaction(s) can be used for the preparation of alkyl halides?
anh. ZnCl
(I) CH3 CH2OH  HCl 
2
 (II) CH3CH2OH + HCl 
anh. ZnCl2
(III) (CH3)3COH + HCl  (IV) (CH3 )2 CHOH  HCl  
[Re-AIPMT-2015]
(1) (IV) only (2) (III) and (IV) only (3) (I), (III) and (IV) only (4) (I) and (II) only
Sol. Answer (3)
The reactions of primary and secondary alcohols with HCl require the presence of a catalyst ZnCl2.
CH3 CH3
11. The reaction CH3—C—ONa + CH3CH2Cl CH3—C—O—CH2—CH3 is called [AIPMT-2015]
—NaCl
CH3 CH3
(1) Gatterman - Koch reaction (2) Williamson synthesis

(3) Williamson continuous etherification process (4) Etard reaction
Sol. Answer (2)
+
In Williamson synthesis, R – O Na + R – X R – O – R + NaX
(ether)
SN2 attact
As attack is SN2  R – X should be less sterically hindered i.e, R – X should be H3C – X or 1° R – X

So,
SN2 attact
CH3 CH3
+
H3C C ONa + H3C CH2 Cl H3C C O CH2 CH3
CH3 CH3
12. Among the following sets of reactants which one produces anisole ? [AIPMT-2014]
(1) CH3CHO; RMgX (2) C6H5OH; NaOH; CH3I
(3) C6H5OH; netural FeCl3 (4) C6H5–CH3; CH3COCl; AlCl3
Sol. Answer (2)
CH3
O Na O
OH
NaOH CH3 – I
(Anisole)
HBr /H2 O2
13. Identity Z in the sequence of reactions CH3CH2CH = CH2  C2H5 ONa
 Y  Z [AIPMT-2014]
(1) CH3–(CH2)3–O–CH2CH3 (2) (CH3)2CH2–O–CH2CH3
(3) CH3(CH2)4–O–CH3 (4) CH3CH2–CH(CH3)–O–CH2CH3
Sol. Answer (1)
Br
HBr / H2O2
H3C CH2 CH CH2 H3C CH2 CH2 CH2
(Y)
CH3 CH2 ONa
H3C CH2 CH2 CH2

O
H2C
H3C

Z is H3C – (CH2)3 – O – CH2 – CH3
14. Among the following ethers, which one will produce methyl alcohol on treatment with hot concentrated H ?
[NEET-2013]
CH3
(1) CH3–CH2–CH–O–CH3 (2) CH 3–C–O–CH 3
CH3 CH3
(3) CH3–CH–CH2–O–CH3 (4) CH3–CH2–CH2–CH2–O–CH3

CH3
Sol. Answer (2)
CH3
H2O/H
15. In the following reaction : H3C–C–CH = CH2
CH3
A + B
Major Product Minor Product
The major product is [AIPMT (Prelims)-2012]
CH3 CH3 CH3 CH3
(1) H3C–C – CH–CH3 (2) H3C–C – CH2–CH2 (3) H3C–C – CH–CH3 (4) CH2–C–CH2–CH3
CH3 OH CH3 OH OH CH3 OH CH3
Sol. Answer (3)
H
+ +
CH = CH2 CH – CH3
–
1 – 2 Ml Shift
CH3 CH3
CH CH3 CH CH3
H2O H2O
CH3 CH3
OH H H3C CH CH3
A OH
16. In the following reactions,

CH3
|
H /Heat
(a) CH3 – CH – CH– CH3   A  B
| Major
product   product 
Minor
OH
HBr, dark
(b) A  C  D
Product  Product 
Major
in absence of peroxide Minor
The major products (A) and (C) are respectively [AIPMT (Prelims)-2011]
CH3 CH3
| |
(1) CH2  C  CH2 – CH3 and CH3  C  CH2 – CH3
|
Br
CH3 CH3
| |
(2) CH2  C  CH2 – CH3 and CH2  CH  CH2 – CH3
|
Br
CH3 CH3
| |
(3) CH3  C  CH – CH3 and CH3  C  CH2 – CH3
|
Br
CH3 CH3
| |
(4) CH3  C  CH – CH3 and CH3  CH  CH – CH3
|
Br
Sol. Answer (3)
As per the reaction sequence

Br
and will form
17. Which one of the following compounds has the most acidic nature ? [AIPMT (Prelims)-2010]
OH
CH2OH OH OH CH
(1) (2) (3) (4)
Sol. Answer (2)
OH
is the most acidic.
18. Which one is most reactive towards electrophilic reagent? [AIPMT (Prelims)-2010]
CH3 CH3 CH3 CH3

OH CH2OH NHCOCH3 OCH3
(1) (2) (3) (4)
Sol. Answer (1)

Due to greater e– releasing effect.
19. Among the following four compounds

a. Phenol b. Methyl phenol c. m-Nitrophenol d. P-nitrophenol
The acidity order is [AIPMT (Mains)-2010]
(1) d > c > a > b (2) c > d > a > b (3) a > d > c > b (4) b > a > c > d
Sol. Answer (1)
Withdrawing group increasing the acidic character and electron donating group decreases the acidic characters.
20. When glycerol is treated with excess of HI, it produces [AIPMT (Mains)-2010]
(1) 2-iodopropane (2) Allyl iodide (3) Propene (4) Glycerol triiodide
Sol. Answer (1)
CH2—OH CH3
CH—OH + HI CH—I
excess
CH2—OH CH3
21. Which one of the following compounds will be most readily dehydrated ? [AIPMT (Mains)-2010]
O O OH OH
O
(1) CH3 (2) H3C
(3) (4) CH3
OH OH CH3 O
Sol. Answer (3)
As carbocation intermediate, more the stability of carbocation, faster the rate of dehydration.
22. Which of the following conformers for ethylene glycol is most stable? [AIPMT (Mains)-2010]
OH OH OH OH
H H OH H OH
H
(1) (2) (3) (4)
H H H HO H
OH H HH H HH H H
Sol. Answer (4)

Intramolecular H-bonding.
23. Consider the following reaction,

(i) H2SO4 room temperature
 Y  Z ;
PBr alc. KOH
Ethanol 
3
 X  (ii) H2O, heat [AIPMT (Prelims)-2009]
(1) CH3CH2–O–CH2–CH3 (2) CH3–CH2–O–SO3H (3) CH3CH2OH (4) CH2 = CH2

Sol. Answer (3)
PBr3
OH Br
Alc KOH
CH2 = CH2
Y H2SO4, H2O
OH
24. Consider the following reaction
CH3Cl Alkaline KMnO4
Phenol 
Zn dust
 X 
Anhydrous AlCl3
 Y  Z
The product Z is [AIPMT (Prelims)-2009]

(1) Benzaldehyde (2) Benzoic acid (3) Benzene (4) Toluene
Sol. Answer (2)
Zn CH3Cl [O]
OH CH3 COOH
AlCl3
X Y Z
25. H2COH.CH2OH on heating with periodic acid gives [AIPMT (Prelims)-2009]

H
(1) 2HCOOH (2) CHO (3) 2 C=O (4) 2 CO2
CHO H
Sol. Answer (3)
OH
+ HIO4.2H2O 2HCHO
OH
26. The major organic product in the reaction, CH3 – O – CH(CH3)2 + H  Product is [AIPMT (Prelims)-2006]
(1) CH3OH + (CH3)2CHI (2) ICH2OCH(CH3)2
(3) CH3O C(CH3)2 (4) CH3 + (CH3)2CHOH
I
Sol. Answer (4)
O OH
+ HI CH3I +
H 3C
27. Ethylene oxide when treated with Grignard reagent yields [AIPMT (Prelims)-2006]
(1) Secondary alcohol (2) Tertiary alcohol
(3) Cyclopropyl alcohol (4) Primary alcohol
Sol. Answer (4)
28. Which one of the following compounds is most acidic? [AIPMT (Prelims)-2005]
OH OH OH
(1) Cl–CH2–CH2–OH (2) (3) (4)
NO2 CH3
Sol. Answer (2)

OH
is the most acidic because of (–M & –I) effect of –NO2.
NO2
29. When 3, 3-dimethyl 2-butanol is heated with H2SO4, the major product obtained is
(1) 2, 3-dimethyl 2-butene (2) cis and trans isomers of 2, 3-dimethyl 2-butene
(3) 2, 3-dimethyl 1-butene (4) 3, 3-dimethyl 1-butene
Sol. Answer (1)
OH –
+ 1 – 2 Ml
+ Shift
+ H
+
30. Decreasing order of reactivity of hydrogen halide acids in the conversion of ROH  RX is
(1) HCl > HBr > HI > HF (2) HI > HBr > HCl > HF
(3) HF > HCl > HBr > HI (4) HF > HBr > HI > HCl
Sol. Answer (2)
R–OH + HX  R – X
The HX reactivity order is HI > HBr > HCl > HF
31. More acidic than ethanol is

(1) CH3CH2CH2CH2CH2CH2CH2CH3 (2) CH3CO2CH2CH3
(3) CH3COCH2COCH3 (4) CH3COCH3
Sol. Answer (3)
CH3
Active methyl more acidic than ethanol.
32. Which reagent converts propene to 1-propanol?

(1) H2O, H2SO4 (2) B2H6, H2O2, OH–
(3) Hg(OAc)2, NaBH4/H2O (4) Aq. KOH
Sol. Answer (2)
? OH
The reagent must be B2H6, H2O2/OH–
33. n-propyl alcohol and isopropyl alcohol can be chemically distinguished by which reagent?
(1) PCl5 (2) Reduction
(3) Oxidation with potassium dichromate (4) Ozonolysis
Sol. Answer (3)
OH
OH
&
[O] [O]
OH O
O
34. Which one of the following will not form a yellow precipitate on heating with an alkaline solution of iodine?
(1) CH3CH(OH)CH3 (2) CH3CH2CH(OH)CH3 (3) CH3OH (4) CH3CH2OH
Sol. Answer (3)
CH3OH + I2 / OH–  No reaction.
35. The general molecular formula, which represents the homologous series of alkanols is
(1) CnH2n + 2O (2) CnH2nO2 (3) CnH2nO (4) CnH2n + 1O
Sol. Answer (1)
CnH2n + 2O is alkanols.
36. On heating glycerol with conc. H2SO4, a compound is obtained which has bad odour. The compound is
(1) Acrolein (2) Formic acid (3) Allyl alcohol (4) Glycerol sulphate
Sol. Answer (1)
CH2 OH
CH2 OH + H2SO4 CHO
(Conc.) (Aclolein)
CH2 OH
37. The correct acidic order of the following is
OH OH OH
I. II. III.
CH3 NO2
(1) I > II > III (2) III > I > II (3) II > III > I (4) I > III > II
Sol. Answer (2)
OH OH OH
> >
NO2 CH3
38. When phenol is treated with CHCl3 and NaOH, the product formed is
(1) Benzaldehyde (2) Salicylaldehyde (3) Salicylic acid (4) Benzoic acid
Sol. Answer (2)
–
OH + CHCl3 + OH OH
CHO
39. The compound which does not react with sodium, is
(1) CH3COOH (2) CH3 – CHOH – CH3 (3) C2H5OH (4) CH3 – O – CH3
Sol. Answer (4)
O
+ Na No reaction
CH 3 CH3
40. Reaction of CH2 – CH2 with RMgX leads to formation of

O
(1) RCH2CH2OH (2) RCHOHCH3
R
(3) RCHOHR (4) CHCH2OH
R
Sol. Answer (1)
OH
+ RMgX R
41. Which of the following will not be soluble in sodium hydrogen carbonate?
(1) 2,4,6-trinitrophenol (2) Benzoic acid (3) o-Nitrophenol (4) Benzenesulphonic acid
Sol. Answer (3)
O
H
Intra H-bonding
O
N
O
Due to presence of intra H-bond, the ‘H’ is engaged, it becomes weak acid. Moreover NaHCO3 is a weaker
base. So, o–nitrophenol does not react with NaHCO3 and hence it is not soluble in NaHCO3.
SECTION - D
Assertion-Reason Type Questions
1. A : p-nitrophenol has high pKa in comparison to o-nitrophenol.
R : In o-nitrophenol, intermolecular H-bonding is present.
Sol. Answer (4)
Intra H–bond
H
OH O O
N
O
>
NO2
Due to intra H bond in o-nitrophenol it is less acidic than p-nitrophenol.
So, Ka (p-nitrophenol) > Ka (o-nitrophenol)
So, pKa order p-nitrophenol < o-nitrophenol
2. A : When C2H5–O–CH3 is reacted with one mole of HI then C2H5OH & CH3I is formed.
R : It is SN1 reaction.
Sol. Answer (3)
The -R gp 3° then only SN1 attack of I– takes place otherwise SN2 attack takes place.
So, in absence of 3°R, that –‘R’ is being attack by I– (or X–) which is less sterically crowded, because the
attack is SN2. Since SN2 reactivity order follows as H3C – I > 1°R – I > 2°R – I > 3°R – I
– HI
Therefore, H3C CH2 O CH3 H3C CH2 OH CH3 I
+
H
I
H3C CH2 O CH3
H SN2 attact
is easy and fast
3. A : When 3, 3-dimethyl butan-2-ol is heated in presence of concentrated H2SO4 then 2, 3-dimethyl but-2-ene is
formed as major product.
R : In this reaction, carbocation is formed as an intermediate.
Sol. Answer (2)
CH3 OH
Conc. H2SO4
H3C C CH CH3 H3C C C CH3
CH3 CH3 CH3
+
+H and –H2O
CH3 Note  2, 3-dimethyl

but-2-ene is formed
because of –CH3 shift
H3C C CH CH3
takes place.
CH3
–CH3 shift
CH3 CH3
+
–H
H3C C CH CH3 H3C C C CH3
CH3 CH3
4. A : In esterification reaction, HCOOH is the most reactive acid among carboxylic acid.
R : Alcohol acts as nucleophile.
Sol. Answer (2)
As in esterification, steric crowding is dominant factor, so smaller is the ‘R’ group of carboxylic acid more is
(RCO2H) the reactivity.
 is most acidic since ‘H’ is smallest.
5. A : Ethers can't be distilled upto dryness due to fear of explosion.
R : Due to the formation of superoxide, it is explosive.
Sol. Answer (3)
Ethers absorb and react with oxygen from air, in presence of light, forming unstable peroxide that can deto-
nate with extreme violence when they become concentrated through evaporation or distillation and disturbed
by heat, shock or friction.
6. A : Phenol does not react with NaHCO3.
R : Phenol is less acidic than H2CO3.
Sol. Answer (1)
Acidic strength order
OH
OH
– +
OH O Na
So, + NaHCO3 + H2CO3
Reaction is not possible.
7. A : CH 3 C COOH gives haloform reaction.
R : It is more acidic than acetic acid.
Sol. Answer (2)

O
With I2 + NaOH and I2 + Na2CO3, the iodoform (or haloform) test is given by pyruvic acid (H3C C CO2H) .
O O O O
I2 + NaOH
H3C C C OH CHI3 + C C + H2O + NaI
+ – – +
Na O O Na
But this reaction is not because that it is more acidic than acetic acid.
8. A : Diphenyl ether is prepared by Williamson synthesis.
R : This reaction generally proceed by SN1 mechanism.
Sol. Answer (4)
Diphenyl ether cannot be prepared by Williamsons's synthesis, because SN2 attack on ‘C’ of benzene is not
possible.
– +
O Na X O
+
Not possible
Wiiliamson's synthesis always follows SN2 attack.
9. A : Grignard's reagent is prepared in the presence of ether.
R : Grignard's reagent is soluble and stable in ether.
Sol. Answer (1)
Grignard reagent is prepared in presence of ether solvent because Grignard reagent (RMgX) is more soluble
in ether solvent and stable as ether doesn't provid 'H+'.
ether
R  X  Mg  R  MgX
CH3 CH3
10. A : CH3 C CH CH2 on hydroboration oxidation gives CH3 C CH CH3 as major product.
CH3 OH CH3
R : It involves the formation of carbocation so undergoes rearrangement.
Sol. Answer (4)
Hydroboration oxidation follows through formation of 4-membered cyclic Ts only and not via carbocation and
hence it gives anti markovnikov addition of H2O on alkene.
CH3 CH3 OH
i.e., H3C C CH CH2 H3C C CH CH2
CH3 CH3
11. A : Two moles of Grignard reagent is consumed in the formation of tertiary alcohol from ester followed by
hydrolysis.
R : One mole of Grignard reagent converts ester into Ketone and second mole of Grignard reagent adds to
Ketone.
Sol. Answer (1)
OH
R C R
R
R
12. A : O bond angle in ether is slightly greater than normal tetrahedral angle (109.5°).
R
R : The hybridisation of oxygen atom in ether is sp3.
Sol. Answer (2)

The B.A. in ether is slightly greater than normal tetrahedral angle 109.5°, this is because of repulsion between
two alkyl group.
CH3 CH3
13. A : CH3 C O CH3 on reaction with conc. HI gives CH3 C I and CH3OH as major product.
CH3 CH3
R : This reaction proceed by SN1 mechanism.

Sol. Answer (1)
CH3 CH3
H3C C O CH3 H3C C I + H3COH
CH3 CH3
+
H
CH3 CH3
CH3
H3C C O H3C C + H3COH
H CH3
CH3
I
CH3
H3C C I
CH3
In case of 3°R the attack of HI is SN1 and takes place at first.
14. A : Ortho-cresol is weaker acidic than meta-cresol.

R : It is due to ortho effect.
Sol. Answer (3)
OH OH
CH3
Acidic order
CH3
(o-cresol) (m-cresol)
This is because of +I effect.

 Ortho effect is found in benzoic acid only.
15. A : Among all ortho halophenol, fluorophenol is least acidic.
R : Ortho-fluorophenol forms intramolecular H-bond.
Sol. Answer (1)
Intra H–bond
F
H
O
Since only - ‘F’ can form H-bond among all halogen, therefore it is least acidic.
16. A : In esterification reaction alcohol act as nucleophile.
R : In this reaction O–H bond of alcohol is broken.
Sol. Answer (1)
In esterification reaction alcohol acts as nucleophile because there is lp present on OH of R – OH and since
O – H bond can be cleaved easily. So, it favours its nucleophility.
Act as Nu
17. A : Phenol is manufactured by Dow's process.
R : It involves the formation of benzyne intermediate.
Sol. Answer (2)
Dow’s process, involves the formation of benzyne intermediate but is not the correct reason.
Cl ONa OH
+
Dow's process 1.NaOH 2. H3O

(P & T)
18. A : Primary alcohol is prepared by the reaction of primary amine with HNO2.
R : Dimethyl amine is a primary amine but does not form methyl alcohol with HNO2.
Sol. Answer (3)
Primary alcohol is prepared by the reaction of primary amine with HNO2.
R  NH2  HNO2  R  OH  N2   H2O
19. A : The reactivity order of alcohols is 1° > 2° > 3° for the reaction in which O–H bond is broken.
R : The reactivity order of alcohol is 3° > 2° > 1° for the reaction in which C–O bond is broken.
Sol. Answer (2)
Reactivity order of alcohols for the reaction in which O – H bond is broken is in the order of
H3C – OH > 1°R – OH > 2°R – OH > 3°R – OH

As the stablity order of their conjugate base.
H3C – O– > 1°R – O– > 2°R – O– > 3°R – O– (because of +I effect of ‘R’ group)
 Reactivity order of alcohol for the reaction in which C – O bond is broken is as
3°R – OH > 2°R – OH > 1°R – OH > H3C – OH
Since stablity order of carbocation.
3°R+ > 2°R+ > 1°R+ > H3C+
20. A : The dehydration of ethyl alcohol in presence of Al2O3 at 633 K gives ethene.
R : The reaction proceed through the formation of carbocation intermediate.
Sol. Answer (3)
OH
Al2O3
H 3C CH 2 H 2C CH2
633 K
OH
H3C CH2 (I°R – OH) prefer to go E2 elimination reaction, so carbocation does not form in this reaction.


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Chapter 11

Alcohols, Phenols and Ethers

(1) (2) HO (3) (4)

HO has only –OH as functional group.

2. Which one is ether?

3. Which one is phenol?

(1) OH (2) H C OH (3) CH2 OH (4) CN

Sol. Answer (1)

4. IUPAC name of HOCH2CH2 OH is

Ethane –1, 2–diol

(1) Benzyl ethoxide (2) Ethoxy benzyl

(Preparation of Alcohols and Phenols)

The reagent used must be H2O + KOH.

9. SN1 mechanism is observed in

Reaction happens via

13. HCHO + A CH2 — OH

(1) Mg — X (2) CH3 (3) OH (4) OCH3

Sol. Answer (1)

Sol. Answer (4)

16. Lucas test is used to distinguish

17. In Lucas test immediate turbidity is caused by

18. Which among the following show tautomerism?

(1) Alcohols (2) Phenol (3) Ethers (4) Anisole

Sol. Answer (2)

This molecule has a chiral centre.

20. ROH + SOCl2 ?

22. Reaction involving cyclic intermediate and anti addition is

Hg(OAc)2/H2O B2H6/ THF

Sol. Answer (3)

This is oxymercuration-demercuration, reaction and involves anti-addition.

23. Boiling point will be least for

(1) OH (2) (3) (4)

24. Which one is most viscous?

25. Lowest boiling point is for

27. 1° alcohols preferably undergo dehydration in presence of Al2O3

28. Which one is inter-molecular dehydration?

30. Phenols can be distinguished from alcohols by

31. Most acidic among the following is

(1) (2) (3) (4)

32. Correct acidic order of acidity is

The reagent X required for above conversion is

(1) LiAlH4 (2) Zn (3) (4) NaBH4

Sol. Answer (2)

34. Electrophile in Reimer-Tiemann reaction

35. In Reimer-Tiemann reaction, the major product is

OH O H Intra - ‘H’ bond

36. Molecule which does not oxidise using PCC

(1) OH (2) OH (3) OH (4) OH

Sol. Answer (1)

Phenol cannot oxidised by PCC.

X and Y respectively are

(Ethers (Preparation and properties)

38. Alcohols and ethers are

Sol. Answer (1)

This presence of chiral centre makes the molecule optically active.

41. Order of nucleophilicity is

OCH3 OCH3 OCH3 OCH3

43. Which one of the following is best Lewis base?

Sol. Answer (2)

This is best Lewis base among the given options.

Sol. Answer (1)

Product A and B are

(1) CH3OH + CH3CH2I (2) CH3I + CH3CH2OH

(3) CH3I + CH3CH2I (4) CH3OH + CH3CH2OH