AMITY INSTITUTE FOR COMPETITIVE EXAMINATIONS

WORK SHEET SANJEEV AWASTHI

CHEMISTRY ALCOHOLS
Choose the correct answer

1. Chromic acid oxidations are believed no proceed through a chromate ester intermeidate. In the oxidation of
ethan-1-ol, the intermeidate which form is
O O
OH O
(a) H C Cr (b) H C Cr
3 O 3 O
O O

O O
O
(c) Cr (d) H C Cr
H3C O OH 3 O
O

2. Compounds ‘A’, ‘B’ and ‘C’ are isomeric alcoholswith the formula C5H12O, ‘A’ react with chromic acid solution,
B forming an acid. The three isomers react with HBr with decreasing relative rates:
C  A  B, all giving the same C5H11Br in varying yields. ‘A’ alone can be oxidised by I2, OH–.
Consider the following molecules:

OH OH
OH
OH H3C H3C
I. H3C II. III. IV.
H3C CH3 CH3 OH CH3 CH3

H3C CH3 OH

V. VI.
H3C OH H3C OH

(a) A – II, B – I, C – IV (b) A – V, B – VI, C – IV

(c) A – III, B – II, C – IV (d) A – V, B – III, C – IV

OH

NaOH CH3  OTs

  
(1 eq)
 Product
3.

OH Cl
The predominant product is
OH OH CH3 CH3
O O

(a) (b) (c) (d)

O Cl OH O
H3C CH3 OH Cl OH OH

Amity Institute for Competitive Examinations Phones: 011-41888030, 41888031, 41888032

-1-
4. Consider the following reactions:
Br Br Br
OH OH OH

I. II. III.

H3C C CH3 H3C C CH3 H3C C CH3

CH3 CH3 CH3
Choose the correct decreasing rate of epoxidation on treatment with OH–/H2O.
(a) I  II  III (b) II  III  I (c) III  II  I (d) II  I  III

5. What results when but-I-ene is subjected to the following reaction sequence

I. Cl2, H2O II. NaOH III. H3O+
(a) Meso compound (b) a 1 : 1 mixture of enantiomeric epoxides
(c) a meso diol (d) a 1 : 1 mixture of enantiomeric diols

CH3


(CH3CO)2 O, H AlCl3
   A
6. O

Find product ‘A’ is

CH3

OH
(a) OH (b)
O CH3
O CH3
H3C CH3 O

CH3

(c) O (d) OH

O CH3

+
H
7. Reaction I: cis-1,2-dimethyl cyclohexane-1,2-diol  A
+
H
Reaction II: trans-1,2-dimethyl cyclohexane-1,2-diol  B
Product ‘A’ and ‘B’ are

(a) same as (b) same as

O
O

(c) respectively and (d) respectively and

O
O
O O

Amity Institute for Competitive Examinations Phones: 011-41888030, 41888031, 41888032

-2-
8. Which of he following reaction gives the alcohol which is lower homologue of the reacting substrate?

CH3 Ph
H O ;H 
(a) H 2O 2 ;H 
(b)
OH 
2 2

 
H3C OH H3C


Ph
H 2O2 ;H 
OH   H 2 O 2 ;H
(c) (d) OH  
H3C Ph


OH KMnO 4 conc. HI
9. A 
one. eq. of CH I
 C9 H10 O3   C9 H10 O 4 
 3,4  dihydroxy benzoic acid
3
(It gives intense colour with (HCO3 so luble)
FeCl3 and Positive Tollen's
test)

Starting substrate ‘A’ is

OH OH

OH OMe

(a) (b)
H3C
CH3 O
CH3
OH O
OH O
CH3

(c) O (d)

CH3
O

10. Identify end product of the following:

(i ) D
(a) CH3CH = CH2   A
( ii ) H O 2

(i ) H 
(b) CH3CH = CH2   B
(ii ) D 2 O

11. NaOH
+ NBS  A   B, What are A and B?

12. Identify end product in the following:

3 BH . THF 6 5 C H CO H
(a) CH3CH = CH2    (b) CH3CH = CH2   3 
H O /OH  2 2 LiAlH /H  4

(c) 4LiAlH /H 
   

O

13. Identify A and B in the following Hydroboration oxidtion (HBO) reaction:

A, B

Amity Institute for Competitive Examinations Phones: 011-41888030, 41888031, 41888032

-3-
14. Identify the final product of the oxymercuration-demercuration of

(a) (b)

Me
(c) (d)

15. Identify A to D in the following reactions:

3CH MgBr 3 3 BH /THF CH MgBr
D    C
H 3O  HgSO
 4 /H 2SO4
  CH3C  CH
   A  
H 2O 2 /OH 
 B
H 3O 

16. Identify A and B in the following reaction:


H 3O
OCH3 + 2CH3CH2MgBr 
(a)  A
O

O
|| H O
(b) PhCCl + 2 3 B
MgCl

CH 3
|
CO, H 2 , [CoH(CO) 4 ] H2
17. CH 3CCH 2C  CH 2       A   B
| | 125  , pressure catalyst
CH 3 CH 3

18. What are the products A, B, C, D and E in the following?

NaBH4
O O CH3OH
NaBH4
 
CH3OH LiAlH4
O
O

O O
OEt   
NaBH4 OEt LiAlH4
CH3OH   
O O

19. What are the various products in the following?

1. O3 /H 2 O/Zn
   
2. LiAlH4



Amity Institute for Competitive Examinations Phones: 011-41888030, 41888031, 41888032

-4-
 AMITY INSTITUTE FOR COMPETITIVE EXAMINATIONS
WORK SHEET
CHEMISTRY ALCOHOLS
O

Br / h Mg CH3–C–CH3 H
Q.1 CH3–CH=CH2 2    
dry ether NH4Cl 
The end product in the above sequence of reaction is
(a) CH2=CH–CH2– C=CH2 (b) H2C=CH–CH= C–CH3
CH3 CH3
OH
(c) H2C=CH–CH2– C–CH3 (d) H2C=CH–CH2– CH–CH2–OH
CH3 CH3

Q.2 OH Hg (OAc) 2

    the major product is
NaBH 4

O
OH OH OH
(a) (b) (c) (d)
OH
OH
Br2 / CCl 4
Q.3 OH     The major product is
O O
(a) Br OH (b) (c) (d)
Br O
Br
Br
18
OH H+
Q.4 The major product is
OH
18
(a) (b) (c) OH (d)
O O18 OH

Q.5 Diols which react with CrO 3 in aqueous H 2SO 4 and yield product that readily undergo
decarboxylation on heating, are
OH
OH
(a) (b) HO (c) HO OH (d)
HO OH OH

Amity Institute for Competitive Examinations Phones: 011-41888030, 41888031, 41888032 1

 18
CH2–Cl AgOCOCH H3O+
Q.11     3  A B+ C. The compounds B and C are:

18
O 18 O
CH2–OH CH2–OH 18
(a) + CH3– C –OH (b) + CH3– C – OH

O 18 O
CH2–OH CH2–OH
(c) + CH3– C –OH (d) + CH3– C –OH

Q.12 C (1) LiAlH4 ? The product is

N   
(2) H 3O 

CH=O
(a) N CH2–NH2 (b) N

(c) N CH=NH (d) N CH2–OH

OH
H
Q.13 Ph—CH—C CH  ? The product is:
(a) Ph–CH=CH–CH=O (b) Ph–CC–CHO
(c) Ph–CH=C=CH–OH (d) Ph–CC–CH2–OH

Q.14 Boiling point of cis-1,3-cyclohexanediol is................ than cis-1,4-cyclohexanediol

(a) lesser (b) greater (c) equal (d) can’t be predicted

Q.15 Cineole is the chief component of eucalyptus oil, it has, molecular formula C10H18O and
contains no double bond or triple bond. It reacts with HCl to give:
CH3
H3C–C–Cl

Cineole HCl


Cl
The structure of cineole is: CH3

CH3 H3C
H3C–C–OH C=CH2 O O

(a) (b) (c) (d)

OH OH CH
CH3 CH3 H3C CH3

Amity Institute for Competitive Examinations Phones: 011-41888030, 41888031, 41888032 3

 HO OH

H
Q.21  ? The major product is:

O
CHO

(a) (b)

OH
O

(c) (d)

O
–
OH Sn / HCl NaNO / HCl
Q.22 + CH3NO2  A     B   2  
 C. The product C is

CH2–NH2
OH O OH
OH CH2–OH
(a) (b) (c) (d)

OH
AgNO
Q.23 CH3–C–CH2–I   3  ? The product is:
Ph
O
(a) CH3–C–CH2 (b) CH3–CH2–C
O
OH Ph
(c) CH 3–C–CH3 (d) CH3–CH–CH2
Ph
CH3CH3
H
Q.24 CH3—C—C— CH3  ? The product is:
O
CH3 O CH3
(a) CH3—CH—C—CH3 (b) CH3—C—C—CH3
OH CH3 CH3

CH3CH3
(c) CH3—C C—CH3 (d) CH3—C—C—CH3
CH3 CH3 OH H

Amity Institute for Competitive Examinations Phones: 011-41888030, 41888031, 41888032 5