Page 1 of 9 CPP - 1_AEP-PH-V

CPP - SHEET
ALCOHOL ETHER & PHENOL — SHEET - 1
OBJECTIVE

1. The decreasing order of acidic character of the compounds CH3C  CH, MeOH, Me2CHOH, Me3COH, H2O is
(a) MeOH  Me2CHOH  Me3COH  H2O  CH3C  CH
(b) CH3C  CH  Me3COH  Me2CHOH  MeOH  H2O
(c) MeOH  H2O  Me2CHOH  Me3COH  CH3C  CH
(d) Me3COH  Me2CHOH  MeOH  H2O  CH3C  CH

2. Which is the correct IUPAC name for the following compound?

OH

(a) 4-iso-Propyl-1, 1-dimethyl-1-pentanol (b) 5-iso-Propyl-1, 1-dimethyl-2-hexanol

(c) 1, 1, 4, 5-tetra-Methyl-1-hexanol (d) 2, 5, 6-tri-Methyl-2-heptanol

3. What reagent would be suitable for distinguishing 1-Methoxy-3-methyl-2-butene from its isomer 4-methyl-3-
penten-1-ol?
(a) Bromine in methylene chloride (b) KMnO4 in aqueous base
(c) AgNO3 in dilute NH4OH (d) Sodium metal suspended in hexane

4. In general, the reduction of ketone to an alcohol can be accomplished by all of the following except one
(A) H2/Pt (B) HIO4
(C) LiAlH4 (D) NaBH4

5. What is product of following reaction?

O
(i) LiAlH4

(ii) H2O


O OH
(A) (B)

OH
OH
(C) (D)

OH

6. Your task is to synthesize 2-phenyl-2-hexanol through a Grignard’s synthesis. Which pair(s) of compounds
listed below would you choose as starting materials?
O O

(a) CH3 (b) CH3

Br and Br and

O Br
(c) and (d) Both (a) and (c)

7. What is the product of the following reaction?

OH
SOCl2

P yridine


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Cl Cl
(a) (b) Cl

Cl
(c) (d)

8. What is the product of the following reaction?

2HBr
 ?
O
(a) 1,3-dibromo butne (b) 1,4-dibromo butane
(c) 1,3-dibromo propane (d) 1,2-dibromo propane

9. Select the best combination of reagents which will bring the following conversion
OH

H3C
(a) CH3Cl/AlCl3; HNO3/H2SO4; Zn/HCl; NaNO2 + HCl; H2O
(b) CH3COCl/AlCl3; Br2/FeBr3; NaBH4/CH3OH
(c) CH3Cl/AlCl3; NBS/hv; LiAlH4/H2O; NaOH
(d) CH3Cl/AlCl3; HNO3/H2SO4; NBS/hv/NaOH

10. The decreasing order of acidic character of the following is:

(I) C6H5CH2OH (II) Me—COOH
(III) PhOH (IV) EtOH
(a) II  III  IV  I (B) II  III  I  IV
(c) I  IV  III  II (d) IV  I  III  II

11. Choose the statement that is correct concerning the following reaction.
Phenol + CH3I/NaOH  Major product
(a) This reaction results in methylation of oxygen in phenol. It is utilized frequently because the hydroxide
group is often highly activated. This reaction can be reversed with HI.
(b) this reaction results in methylation of oxygen in phenol. The resulting product is activated approximately
the same amount as in phenol. The reaction can be reversed with HI.
(c) This reaction results in methylation of oxygen in phenol. This reaction can be reversed with HI.
(d) This reaction results in an SN2 reaction between methyl iodide and NaOH. The resulting iodide ion
substitutes at ortho and para positions of phenol. Treatment of this product with reaction.

12. A mixture of toluene, benzoic acid, aniline and phenol was dissolved in diethyl ether and extracted with 5%
NaHCO3 solution. This extract was acidified until a white crystalline compound appeared. What is the identify
of this compound?
(a) Toluene (b) benzoic acid
(c) Aniline (d) Phenol

13. In which of the following reaction(s), reactant and products are correctly matched?
O

OH O C CH3
(a)
NaOH (CH3CO)2 O
 CCl4  
H2O
 H Heat

COOH
OH OH
CH3CH2Br
(b) (1.0 mol)  NaOH(aq) 
 (1.0 Mol)

COOH COO2H5
OH Br
O
Br
(c)  NaOH(aq) 

OH O
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OH OH
CO2 CH3COCl
 NaOH    
O CH3
(d)

O O

14. Which of the following can bring about deuteration of phenol at para position
OH OH

Dil. D2SO4
(a)  Conc. H2SO 4   


D
OH OH

CS2 Mg D2O
(b)  Br2 
AlCl
 
Ether
  
3

D
OH OH

CH3I Cl2 Mg D2O Dil. H2SO4

(c)  NaOH   
AlCl
 
Et O
   
3 2

D
OH OH

Zn
(d) 
DCl


Br D

15. Which of the following is/are true regarding phenol?

(a) It turns pink anexposure to air
(b) It is less reactive than anisole in aromatic electrophilic substitution reaction
(c) It is more reactive than aniline in an aromatic electrophilic substitution reaction
(d) Acetylation of phenol decreases its reactivity in aromatic electophilic substitution reaction

16. Which of the following is produced during the following reaction?

575 K
CO(g) + H2(g) 
ZnO, Cr2O3
 ... ?
(a) Ethanol (b) Ethnanl
(c) Methanol (d) Methanal

17. The major thermodynamic product of the reaction given below is

OH O

H3C OH

Heat


(a) (b)

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(c) (d)

18. What are (A) and (B) in the following reaction

Cl
Mg / Et O
  
2
 (A) (
i ) CH 3 CHO
  (B)
( ii ) aq. NH 4 Cl
Br
MgCl CHOHCH3 Cl Cl

(a) (b) and

and
Br Br MgBr CHOHCH3
MgCl MgCl

(c) (d) None of these

and
Br CHOHCH3

MgBr CH2CH2OH
19. forms on reaction with
CH2  CH2
(a) CH3  CHO (b) O

(c) CH3  CH2  CHO (d)

O

20. A saturated ether which cannot be prepared by williamson’s synthesis is

(a) CH3  O  CH3 (b) C2H5  O  C2H5
(c) (CH3)2CH O  CH(CH3)2 (d) (CH3)3C  O  C(CH3)3

21. Which of the following will not be soluble in sodium bicarbonate solution
OH —COOH
(b)
O2N NO2

(a)

NO2
OH SO2OH

(c) (d)

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Page 5 of 9 CPP - 1_AEP-PH-V
SUBJECTIVE
1. Write the structure and IUPAC name of Glycol and Glycerol.

2. Which of the following is a strongest acid and why?

(a) OH (b)
HO

OH HC
(c) (d)
OH

3. Arrange the following

i) H2O, CH3OH, C2H5OH,(CH3)3COH (in acidic strength)
ii) ClCH2CH2OH, CH3CH2OH, NO2CH2CH2OH

4. Why an aliphatic alcohol is usually weaker acid than aromatic alcohol?

5. Complete the reaction


H2O / H
(a) Et — O — Et  

O
(b) 
H2O / H
R C OR  

H2 / Pt
(c) R — CHO 

H2Ni
(d) R2 CO  

(e) H2 / Pt
CHO 

CN O
(f)
H2 / Pt


H2 / Ni
(g) CHO 
(1 eq)

(h) LiAlH4
CHO 
H2O

O
LiAlH4

HO
2
(i)

H2 / Pt


NaBH4
COOH  
(j) H2O

LiAlH4

H2O

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O
(k) LiAlH4

H2O

HCl
(l) CH3CHO + LiAlH4 
H2O


HCl
(m) CH3 CHO  LiAlD4 
H2O


DCl
(n) CH3 CHO  LiAlH4 
D2O


LiAllH4
HCl


(o) CH3 COCH2 CH2COOCH3
NaBH4

HCl


6. Show how you would synthesize the following alcohols by adding appropriate grignard reagent to
formaldehyde (Write complete reaction)

CH2OH
(a) (b)
OH

CH2OH
(c)

dil H2SO4
7. CH CH CH3   ? (with mechanism)

8. Give structure of the principle product (s) when each of the following alcohol reacts with
i) Na2Cr2O7/H2SO4 ii) PCC
(a) 1-octanol (b) 3-octanol
(c) 2-cyclohexen-1-ol (d) 1-methyl cyclohexanol

9. Draw structural formulas for the products formed when each compound is heated or reflux in concentrated HI.

CH3 O
HI
(a) O
HI

1 eq.
 (b) 
1 eq.


O
HI HI
(c) O 
1 eq.
 (d) 
excess

O

10. Complete the following reactions.

HCl
a) HO NO 2  CH3OMe 
H2SO4



OH
O
NaOH
b)  ?  O
OH O

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K2CO3 Heat
c) C6H5OH + CH2 = CH — CH2Br  

OH OH

H2SO4
d)  ?  


CMe3

11. What is meant by steam distillation? (b) What physical property most influences the ability of a compound to
be steam distilled? (c) Which isomer (o, m, or p) of hydroxacetophenone steam distils?

12. Predict product of the following reaction.

OH


NaOH H3O
 CHCl3    ?

13. Pyrrole also undergo Reimer-Tiemann’s reaction like phenol but besides a normal formylation, some unusual
reaction occur simultaneously forming the 2nd product in the following reaction.
Cl

OH
 CHCl3   CHO 
N N
H H N
Explain the formation of chlorpyridine in the above reaction.
——
ANSWER KEY
OBJECTIVE
1. C
2. D
3. D
4. B
5. B
6. A
7. D
8. C
9. A
10. B
11. A
NaOH CH3I HI
C 6H5  OH  
SNI
 C 6H5 OCH3  C6H5 OH  CH3I
12. B
Only benzoic acid forms salt with NaHCO3, hence comes in aqueous phase which reprecipitate on
acidification.
13. A, C
14. A, C
15. A, D
16. C
17. D
18. B
19. B
20. D
21. C

SUBJECTIVE
2. D
3. i) CH3OH  H2O  C2H5OH  (CH3)3COH
ii) NO2CH2CH2OH  ClCH2CH2OH  CH3CH2OH
4. Because phenoxide ion is more stable due to resonance.

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5. (a) EtOH
(b) RCOOH + ROH
(c) R—CH2OH

OH

(d) R C R

(e) CH2OH

H2NH2C HO
(f)

(g) CH2OH

(h) CH2OH

OH OH

(i)

OH OH
(j)
COOH, CH2OH

OH
(k)

(l) CH3CH2OH

(m) CH3CHDOH

(n) CH3CH2OD

(o) CH3CH(OH)CH2CH2CH2OH + CH3OH, CH3CH(OH)CH2CH2COOCH3

H H
O
Br MgBr
H C OMgBr
 Mg 

(C2H5 )2 O

H
6. (a)
H2O / H

CH2OH  Mg(OH)Br

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(b) Br Mg MgBr 

(i) HCHO

  (ii) H O /H 
Et 2O 2
OH

Br
(c) (1)Mg/ Et 2 / O
OH

(2) HCHO

(3) H2O /H

OH

7. CH CH3  H  C CH2CH3 

H O
2
 C CH2CH3

H H H
8. (a) (i) Octanoic acid (ii) Octanal (b) (i) 3-octanone (ii) 3-octanone

(c) (i) O (ii) O

(d) No reaction
OH
9. (a) C2H5I + C3H7OH (b) C 2H5I 

CH2I
(c) (d) CH2 = CH2
OH

10. a) H3C O NO 2

b) COCl2
OH
c)

d) CH2 = C(CH3)2
11. When steam carries with its compounds that are mixed with boiling wer but not dissolved, the compounds are
said to steam distill. (b) The steam-distilled compound must have an appreciable vapour pressure at the
boiling point of water, (c) Attraction to water greatly lowers the vapour pressure, preventing steam distillation.
O nl y t he chel at ed o -i som er has a m i nimal att r acti on wi t h wat er and st eam di stil s.
H
O O

CH3

Chelate of o-hydroxacetophenone

12. OH Cl
, ,  Ph3PO4

——

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