ETHER HANDOUT

1. Write the name of given structures:

O O O

(I) (II) (III)

2. Arrange the following in decreasing order of bond angle.

O O O O
H3C x CH3 H3C y H H z H Ph w H

3. CH3ONa + CH 3Br
4. ONa +
Br

- +
O Na

5.
+ CH3Br

Br

6.
CH3ONa +

7. t - BuOK + CH3Br
8. t - BuOK + C2H5Br
Br
9.
t - BuOK +

10. CH3ONa +
Br

11. Ag 2O
2CH3Br
(dry)
conc. H2SO 4
EtOH
o
140 C
12.
conc. H 2SO 4
o
160 C
OH

13. C2H5ONa
C2H5Br

OH

14. (CH 3) 2SO 4

+
H
 CH3OH
15. +
O H
1) Hg(OAc) 2/MeOH
16.
2) NaBH4
17. m - CPBA

Ag/O 2

18. CH3
anhydrous HI
H3C O CH3
CH3

conc. HI
(cold)
19. CH3
conc. HI
H3C O CH3
(Hot)
CH3
20. HI
O
(cold)

HI
(excess)
21.
Ph HI
O (cold)

HI
(Hot)
22.
conc. HI
(cold)
O
CH3
conc. HI
(Hot)
23. OCH3

conc. HI
(cold)

conc. HI
(excess)
24. O
HI
(cold)

HI
(excess)
25. HI (excess)
MeO OMe
OMe
CH2.OH
HI (excess)
26. CH.OH
CH2.OH
-
27. O OH

CH3M3Br

1) LiAlH 4
2) H2O
NaBH4
H2O
HBr

28. O HI
(cold)

HI
(excess)
29. O HI (excess)

HBr (excess)

-
30. O OH

CH3M3Br

LiAlH 4

HBr

+
H , H 2O

+
H , MeOH
 -
31. O OH

CH3M3Br

LiAlH 4

HBr

+
H , H2 O

+
H , MeOH

32. O NaBH4

O NaBH4

O NaBH4

33. Calculate the total moles of HI consumed in given ethers

OCH3
'x' HI
A)
OCH3

OCH3
'x' HI
B)
OCH3
OPh
'x' HI
C) H3C O CH2CH2CH2 O CH3
'x' HI
D) H3C O CH2CH2 OCH 3
O
'x' HI
E)
O
O
'x' HI
F)
O
OCH 3
'x' HI
G)
OCH 3
34. Draw the product structure of hydrolysis of given ethers
OCH3 +
H , H2 O
A)
OCH3
 OCH3 +
H , H2 O
B)
OH
OMe
OMe +
H , H2 O
C)
O +
H , H 2O
D)
O
+
H , H 2O
E) O CH CH2

+
H , H 2O
F) O

+
H , H2O
G) O

35. + -
OMe N2 - Cl

+ -
OMe N2 - Cl

O2 N NO 2
36. +

NO 2
37. OMe

CH3Cl
AlCl3 (anhyd)

CH3COCl
AlCl3 (anhyd)
O
14
38.

O
13
39. 14
P+Q+R
 JEE MAINS PREVIOUS YEAR QUESTIONS
1. The major product [B] in the following reactions is:
CH3
HI H2SO4
H3C CH2 CH CH2 CH2 CH3 [A] alcohol [B]
Heat
CH3
C
A) CH 2 = CH 2 B) H3C CH CH3

CH3

C) H3C CH2 C CH2 D) CH 3 CH 2 CH = CH CH 3

2. The major aromatic product C in the following reaction sequence will be :
O
HBr
(excess), (i) KOH (Alc.)
A + B
(ii) H

O3
C
+
Zn/H 3O

OH OH

CO2H
A) CHO B)
Br Br

CO2H
C) D) CHO

3. An organic compound 'A' (C9 H10O) when treated with conc.HI undergoes cleavage to
yield compound 'B' and 'C'. 'B' gives yellow precipitate with AgNO 3 where as 'C'
tautomerizes to 'D'. 'D' gives positive iodoform test. 'A' could be:

O CH2 CH CH2 O CH CH CH3

A) B)

CH2 O CH CH2 H3C O CH CH2

C) D)
4. Among the compounds A and B with molecular formula C9 H18O 3 , A is having
boiling point the B. the possible structures of A and B are:
A) A HO OH B) A H3CO OCH3

HO OCH3

B H3CO OCH3 B HO OH

OCH3 HO
C) D) A H3CO OCH 3
A HO OH

HO OCH 3

B HO
B HO OH
OH

OH
OH
5. 1-methyl ethylene oxide when treated with an excess of HBr produces:
Br Br
Br
A) B)
CH3 CH3
Br
CH3
C) Br D)
Br
6. The major product of the following reaction is:
O
HI (excess)

NC O

OH I

A) B)

NC OH NC OH
 OH I

C) D)

NC I NC I
7. The major product obtained in the given reaction is:
H3C O CH2 CH3
CH2 CH AlCl 3
Product
Cl

A) H3C O CH CH3
CH2 CH

B) H3C O
CH2
CH
C CH2

C) H3C O

CH3
D) H3C

H3C O

8. The major product of the following reaction is:

OCH3
conc. HBr (excess)
heat

HC CH2

Br OH

A) B)
Br CHCH 3 Br CHCH 3
Br OH

C) D)
CH2CH2Br CH2CH2Br
9. The major product of the following reaction is:
CH3O
(1) Cl2/CCl4
(2) AlCl3 (anhyd.)

Cl

CH3O

A) CH3O B)
Cl

Cl

CH3O

C) CH3O
D)
Cl

10. The major product in the following conversion is:

HBr (excess)
CH3O CH CH CH3 ?
Heat

HO

A) HO CH2 CH CH3 B) HO CH CH2 CH3

Br Br

C) CH3O CH CH2 CH3 D) CH3O CH2 CH CH3

Br Br
11. The major product in the following reaction is:

CH3O
CH 2Cl (i) AlCl 3 (anhyd.)

(ii) H 2O

OCH 3
CH3
A) CH3O B)

CH3O CH3O

C) D)
CH3
12. The major product formed in the following reaction is:
 O HI
Heat
O

A) OH B) I

OH I

C) OH D) I

I OH
13. Consider the reaction sequence below:
OCH 3

Succinic anhydride Clemmenson's

A X, is
AlCl 3 reduction

OCH 3 OH OH
CH3O

A) B)

OH OH
OCH 3
CH3O

C) D)
 JEE ADVANCED PREVIOUS YEAR QUESTIONS
14. The acidic hydrolysis of ether (X) shown below is fastest when

acid
OR OH + ROH

[X]

A) one phenyl group is replaced by a methyl group.

B) one phenyl group is replaced by a para-methoxyphenyl group.
C) two phenyl groups are replaced by two para-methoxyphenyl groups.
D) no structural change is made to X.
15. The major product of the following reaction is
RCH2OH
+
O H (anhydrous)

A) a hemiacetal B) an acetal C) an ether D) an ester

16. List-I contains reactions and List-II contains major products.
List-I List-II
P) 1)
+
ONa Br OH

Q) 2)
+ HBr
OMe Br

R) 3)
+ NaOMe
Br

S) 4) O
+ MeBr
ONa

Match each reaction in LIST-I with one or more products in LIST-II and choose the
correct option.
A) P-1,5; B-2; R-3; S-4 B) P-1,4; Q-2; R-4; S-3
C) P-1,4; Q-1,2; R-3,4; S-4 D) P-4,5; Q-4; R-4; S-3,4
17. Match the chemical conversions in List I with the appropriate reagents in List II and
select the correct answer using the code given below the lists:

List-I List-II
P) 1) (i) Hg(OAc) 2 ;(ii) NaBH 4
Cl

Q) 2) NaOEt
ONa OEt

R) OH 3) Et-Br

S) 4) (i) BH 3 ;(ii) H 2O 2 / NaOH

OH

P Q R S P Q R S
A) 2 3 1 4 B) 3 2 1 4
C) 2 3 4 1 D) 3 2 4 1
18. Which of the following is/are true statement(s)
F OCH 3

NaOCH 3
Intermediate

NO 2 NO 2

A) the intermediate is aromatic

B) the intermediate is resonance stabilized anion.
C) electron withdrawing group on benzene ring stabilize the intermediate.
D) this is elimination-addition reaction.
 KEY
1 2 3 4 5 6 7 8 9 10
B A C A B C C B D B
11 12 13 14 15 16 17 18 19 20
D D D