Alchol TesOct 2014

UL-39,40, Surya Kiran Aptt., Ghod Dod Road, SURAT.

120 Marks

90160 75973, 9427850833

1.

Action of water in the presence of sulphuric acid with the following alkenes
CH 3
(i) CH 3 CH C
and (ii) CH 3 CH CH 2 gives
CH 3
CH 3

(a) (i) CH 3 CH 2 C
|
OH

and
CH 3

(ii) CH 3 CH CH 3
|
OH

CH 3

(b) (i) CH 3 CH CH
|
OH

(ii) CH 3 CH 2 CH 2OH

and
CH 3

CH 3

(c) (i) CH 3 CH CH
|
OH

and
CH 3

(ii) CH 3 CH CH 3
|
OH

CH 3

(d) (i) CH 3 CH 2 C
|
OH
2.

and (ii) CH 3 CH 2 CH 2OH

CH 3

Which one of the following reactions would produce secondary alcohol

(a)

O
O
(b)
||
.
||
.
1. CH 3 MgBr
1. LiAlH 4
C6 H 5 CCH 3

C6 H 5 CCH 3

2. H

3.

4.

2. H

(d)

O
||

1 . OH

C6 H 5 CCH 3

2. H

2 . Br2

Propene, CH 3 CH CH 2 can be converted to 1-propanol by oxidation. Which set of reagents among the following is ideal
to effect the conversion
(a) Alkaline KMnO 4

(b) B 2 H 6 and alkaline H 2 O2

(c) O 3 / Zn dust

(d) OsO 4 / CH 4 , Cl 2

[ CBSE 1991]

The compound that will react most readily with NaOH to form methanol is

(a) (CH 3 )4 N I
5.

1. LiAlH4
(c) CH 3 CHO

[IIT Screening 2001]

(b) CH 3 OCH 3

(c) (CH 3 )3 S I

(d) (CH 3 )3 Cl

Which is hydrolysed at the fastest rate

Cl
Cl
(a)

6.

(b)

Cl
(c)

(d)

HBO, oxymercuration-demercuration and acid catalysed hydration will give same product in
(a)

(b)

(c)

(d)

SeO 2

A, A is

7.

OH
(a)

OH

(b)

OH

(c)

(d)
OH

8.

Cl

O
O
COOH

AOis
O
CH2OH

(a) B2 H6 / H 2O

(b) LiAlH4

(c) CH 3OH / Na

(d) P / HI

CH 2CH 3
|
H O
9. CH 3 CHCH CHCH 3 3
Major product of this reaction
(a) Is optical isomer
(b)
(c) Is dehydrated easily
(d)
10. Consider the following methods
I : Hydration of olefins
II :
III :
Reduction of carbonyl compounds
Which of these can be used to prepare alcohols
(a) I, II and III
(b) I and II
(c)
11. Rate of hydration of

CH CH 2,

Gives white turbidity with HBr immediatly

All correct
Hydrolysis of cyanides

II and III

(d) I and III

CH 3
|
C CH 2 ,

CH CHCH 3,

(I)
will be in order
(a) I<II<III

(II)
(b) I<III<II

(III)
(c) II<I<III

(d) III<II<I

O
CH MgBr (excess )
O
3 X, X is
H 3O

12.

H3C
(a)

H 3C

OH

(b)

H3C
O

OH

H 3C
O

OH

(c)

(d)
CH3

H O
CH CHCH 3 3 A (major)

13.

(a)

(b)

CH 2 CH CH 3
|
OH

(c)

CH CH CH 3
(d)
|
|
OH OH
CH 3 MgBr (excess )
A. A (alcohol) can also be obtained by
14. (C 2 H 5 O ) 2 CO
H 3O
CH MgBr (2 mol )
(a) CH 3 CH 2 CHO 3
H 3O

O
||
CH MgBr (1 mol )
(c) CH 3 CCH 3 3
H 3O

15.

CH CH 2 CH 3
|
OH
CH 2 CH 2 CH 2 OH

O
||
CH MgBr (2 mol )
(b) CH 3 C OC 2 H 5 3
H 3O

(d) As in (b) and (c)

H O
Ester A(C 4 H 8 O 2 ) CH 3 MgBr 3 C 4 H 10 O
(2 parts)

(alcohol B)
Alcohol B reacts fastest with Lucas reagent. Hence A and B are
O
||
(a) CH 3 COC 2 H 5 , (CH 3 )3 COH

O
||
(b) H COC 3 H 7 , (CH 3 )2 CHOH

O
O
||
||
(c) CH 3 COC 2 H 5 , (CH 3 )2 CHOH
(d) H COC 3 H 7 , (CH 3 )3 COH
16. Which one of the following compounds is most rapidly hydrolysed by SN 1 mechanism

(a) CH 3 CH CHCl

(b) CH 2 CHCH 2 Cl

(c)

CH 2 Cl

(d) (C 6 H 5 )3 CCl

CH 3

17.

CH ONa
CH 3 C CH 2 3
X ,
CH 3 OH

X is

CH 3
|
(a) CH 3 CCH 2 OCH 3
|
OH
O
O

18.

CH 3
|
(b) CH 3 CCH 2 OH
|
OCH 3

OH

(c) CH 3 CH CHOH
|
|
OCH 3 CH 3

(d) None is correct

(c)

(d) CH 3 OH / Na

OH
OH

O
Reagent A used in this change is
(a) B 2 H 6
(b) LiAlH 4

Sn / HCl

CH 3

19.

H O18
CH 3 C CH 2 2
A,
H

A(with position of 18 O) is

O
CH 3
|
(a) CH 3 C CH 2
| |
18
OH OH

CH 3
|
(b) CH 3 C CH 2
|
|
OH 18 OH

CH 2 OH
(c) CH 3 C CH 2

(d) No reaction

18

20.

HO
OH
Select X and Y out of I : MnO 4 / OH
21.

(a) I, II
Dehydration of alcohols

(b) II, I

OH

22.

II : HCO 3 H

OH

HO
(c) II, II

OH

(d) I, I

OH

(I)
(II)
(III)
will be in order
(a) I<II<III<IV
(b) I>II>III>IV
In the following case configuration about chiral C(*) is retained
Me
Na
CH 3 Br
*
(a) H
OH

Et

OH
(IV)

(c) III<II<I<IV

(d) II<III<IV<I

Me

(b) H

TsCl
CH 3 ONa
OH

Et

Me

(c)

PCl5
CH 3 ONa
OH

(d) In none case

Et

CH 3
|
conc. H 2 SO 4
23. CH 3 C CHCH 3

A (predominant), A is
|
|
CH 3 OH

(a) (CH 3 )3 CCH CH 2

OH

24.

(b) (CH 3 )2 C C(CH 3 )2

(c) CH 2 CC H 2 CH 2 CH 3
|
CH 3

(d) None is correct

(c)

(d)

MnO2

A, A is

OH
(a)

OH
O

(b)

O
OH

O
O

O
OH

OH

25.

conc. H 2SO4

products can be

(a)

26.

(b)

(c) Both correct

(d) None is correct

(c) CH 2 CH CC H 2 CHO
||
O

O
||
(d) CH 2 CH CC H 2 C OH
||
O

(c) Both are true

(d) None is true

MnO2
CH 2 CH CH CH 2 CH 2 OH

A. A is
|
OH

O
||

(a) CH 2 CH CC H 2 CH 2 OH (b) CH 2 CH CH CH 2 CHO

|
||
H
OH
CO , H , [CoH (CO )4 ]
H2

Product
27. CH 3 CH CH 2 2
Cu Zn
125 o , pressure

This represents oxo method of alcohol synthesis. Product can be

(a) CH 3 CH 2 CH 2 CH 2 OH

OH

28.

In this dehydration reaction

(a) H 2 O
H3C
29.

(b) CH 3 CH CH 2 OH
|
CH 3
H PO4
3

18

O will be in
(b) A

+ H2O
A
(c) Both

(d) None

CH 3
|
(c) CH 3 C OH
|
CH 3

(d) No reaction

LiAlH4
CH
2

A, A is

H3C
O

(a) CH 3 CH CH 2 OH
|
CH 3
CH 3
|
30. CH 3 C CH CH 2 CH 3
|
CH 3

This change can be done by

(a) Acid catalysed hydration
(c) Hydroboration-oxidation

(b) CH 3CH 2CH 2CH 2OH

CH 3
|
C CH CH 3
|
|
CH 3OH

(b) Oxymercuration-demercuration
(d) Any method mentioned above

ALCOHOL ANSWER KEY

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ALCOHOL ANSWER KEY

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ALCOHOL ANSWER KEY

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ALCOHOL ANSWER KEY

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ALCOHOL ANSWER KEY

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ALCOHOL ANSWER KEY

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ALCOHOL ANSWER KEY

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