155

3
GRIGNARD REAGENT

Level - 1
1. What is the major product of the following reaction ?
O
CH MgI
3 3H OÅ
¾ ¾¾ ¾® ¾ ¾¾ ¾®
Et 2O

CH3 OH
(a) (b)
CH2 – OH CH2 – CH3

O
CH3 OH
(c) (d)
CH3
CH3

CH3
C – OCH3
PhMgBr
2. O ¾ ¾¾¾® (P). Product (P) is :
(1 equivalent)

CH2 – COCH3
O

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 CH3 O CH3 O

C — Ph C — Ph
(a) (b)
CH2 — COCH 3 CH2 — COCH3
O O
CH3 CH3
C — Ph C — OCH3
(c) O (d) O
CH2 — COCH 3 CH2 — C — Ph
CH3 ||
O O

O OH
SH SH | CH3
C – Cl C
HO 1. x CH3MgBr CH3
3. Reaction- 1 ; 2. H3OÅ OH CH3
C – Cl C
| CH3
O OH
O OH
C — O — Et CH3 — C — CH 3

1. y CH3MgBr
Reaction- 2 ; 2. H3OÅ

CH3
CH2 — Cl

What is the ratio of (x y) in above problem ?

(a) 1.5 (b) 2 (c) 2.5 (d) 3
4. In which of the following reaction 2° alcohol is obtained as a product ?

(1) CH MgBr (1) MgCl

3
(a) ¾ ¾¾¾¾¾® (b) CH3 O
(2) H 2O
(2) H 2O
O
O
(1) CH MgBr
3
(c) ¾ ¾¾¾¾¾® (d) Both (a) and (b)
(2) H 2O

5. What product would you expect to obtain from Grignard reaction when an excess of
phenylmagnesium bromide reacts with dimethyl carbonate CH 3 OCOOCH 3 ?
OH OH OH O
| | | ||
(a) CH 3 — C — Ph (b) CH 3 — CH — Ph (c) Ph — C — Ph (d) CH 3 — C — Ph
| |
Ph Ph

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6. In which of the following reactions product formed is same ?
O
MgX
MeMgX
(i) P (ii) P
O
O
||
(iii) MgBr ¾¾® P

(a) (i) and (ii) (b) (ii) and (iii) (c) (i) and (iii) (d) (i), (ii) and (iii)
7. Which of the following reaction sequences would be the best for synthesis of 2-pentanone ?
O
|| CH 3 MgI H 3O Å
(a) CH 3 — CH 2 — CH 2 — C — H ¾ ¾¾ ¾® ¾ ¾¾ ¾®
Et O 2
CH 2 — CH 2
CH 3 MgI H 3O Å
(b) | | ¾ ¾¾ ¾® ¾ ¾¾ ¾®
Et 2O
CH 3 — CH — O
3 3 CH MgI H OÅ
(c) CH 3 — CH 2 — CH 2 — C ºº N ¾ ¾¾ ¾® ¾ ¾¾ ¾®
Et 2O
O
|| CH 3 MgI H 3O Å
(d) CH 3 — CH 2 — C — H ¾ ¾¾ ¾® ¾ ¾¾ ¾®
Et 2O
(Propanal)

OH
CO2CH3 C(CH3)2
x CH3MgI
8. ; Dimethyl phthalate
H+
CO2CH3 C(CH3)2
OH
Number of moles ( x) of Grignard reagent consumed in the above reaction is :
(a) 2 (b) 3 (c) 4 (d) 5
OH
|
9. Ph — C — CH 3
|
CH 2 - CH 3
Which of the following combinations can not be used to prepare alcohol given above ?
O
||
(a) PhMgBr + 2-butanone ¾ ¾¾ ¾® (b) EtMgBr + Ph - C -CH 3 ¾ ¾¾ ¾®
NH 4Cl NH 4Cl
O O
|| ||
(c) CH 3 MgBr + Ph - C -Et ¾ ¾¾ ¾® (d) EtMgBr + Ph - C -CH 2 - CH 3 ¾ ¾¾ ¾®
NH 4Cl NH 4Cl

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 O
|| (1) CH 3 MgBr
(excess)
10. Et — O — C — O — Et ¾ ¾¾¾¾ ¾® (A), Product (A) is :
Å (2) H 3O

O O
|| ||
(a) CH 3 — C — O — Et (b) CH 3 — C — CH 3
OH
|
(c) CH 3 - C - CH 3 (d) CH 3 — CH 2 — CH 3
|
CH 3
O
O O
H+
11. PhMgBr + ¾® (A). Product (A) is :
¾¾
excess

O OH OH O
|| | | ||
(a) Ph — C — Ph (b) Ph— C — Ph (c) Ph – C (d) Ph – C – O
| |
Ph Ph
O
12. C – NOCH3 + CH 3 MgBr ¾ ¾¾¾ ¾® ( P ) . Product (P) is :
5% HCl
| Methyl magnesium H 2O > 90%
CH3 bromide 75 equivalent

N-Methoxy-N-methyl
benzamide 1-equivalent

OH OH O O
| | || ||
(a) Ph— C — Ph (b) Ph— C — CH 3 (c) Ph — C— CH 3 (d) Ph — C — Ph
| |
Ph CH 3
13. Point out the incorrect synthesis :
OH
MgBr O
||
(1) CH 3 -C -CH 3
(a) ¾ ¾¾¾¾¾
+
¾®
( 2) H

OH
|
Br CH – Ph
(1) Mg,ether
(b) ¾ ¾¾¾¾®
(2) Ph -CHO
N (3) H 3O Å N
|
H H

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 CH2 – CH2
(1)
¾¾¾¾¾® O
(c) PhMgBr + Ph — CH 2 — CH 2 — OH
(2) H+

(1) HCHO
(d) PhMgBr + ¾ ¾¾
¾+
® Ph — CH 2 — OH
(2) H

O
|| 14
NaH CO 3 (i) PhMgBr
14. CH 3 — C — O — H ¾ ¾¾¾ ® ( A) ¾ ¾¾¾¾® (B)
(gas) ( ii) H 3O Å

O
|| 14
NaH CO 3 (i) PhMgBr
CH 3 — S — O — H ¾ ¾¾¾ ® (C ) ¾ ¾¾¾¾® (D)
|| gas ( ii) H 3O Å
O
Product (B) and (D) in the above reaction are :
O O O O
|| || || ||
(a) Ph — C— O — H, Ph — S — O — H (b) Ph - C - O - H, Ph - S - O - H
|| 14
O
O O O O
|| || || ||
(c) Ph — C— O — H, Ph — C — O — H (d) Ph — C — OH, Ph — S — O — H
14 14
(1) MeMgBr,
OH THFOºC
15. (A); Product (A) in this sequence is :
OEt OLi
(2)

(3) H+,
O
O

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

OH
OH

3 CH MgBr
4 NH Cl
16. ¾ ¾¾¾¾® ¾ ¾¾¾® Products.
diethyl ether H 2O
CH3

Comment on optical activity of the products. They are :

(a) racemic mixture (b) diastereomers
(c) meso forms (d) optically inactive due to absence of chiral centre

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17. In which of the following reaction an acid-base reaction takes place ?
CH2MgCl
H H
O
HBr in water
(a) (b)

O
Li
MgCl D
O

(c) (d) All of these

(1) 2PhMgBr
2 4 H SO
18. ¾® A ¾ ¾¾
¾ ¾¾¾¾ ¾ ® (B), Product (B) in this reaction is :
(2) H 2O D
O O
18

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

O Ph O Ph O Ph O Ph
18 18

19. All of the following compounds react with ethylmagnesium bromide. Alcohols are formed
from three of the compounds. Which one does not give an alcohol ?
O O
(a) CH (b) COCH3

O O
|| ||
(c) CH2OCCH3 (d) Ph - O - C - O - H

20. A student was carrying out a Grignard reaction between PhMgBr and ethyl benzoate. She ran
out of anhydrous ether just after the Grignard reagent was made. Which of the following
solvents can still be used to dissolve the ethyl benzoate for its reaction with already formed
PhMgBr ?
(a) acetone (b) ethyl acetate (c) absolute alcohol (d) benzene
OH H Ph Ph OH H
MeO2C N N tBu
t–Bu HO
(1) x PhMgBr
21. ¾ ¾¾¾¾
¾®
(2) H 3O Å
HO HO
Number of equivalents of Grignard reagent ( x) used in reaction (1) is :
(a) 3 equivalent (b) 4 equivalent (c) 5 equivalent (d) 6 equivalent

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 OH
|
Br CH – Ph
(1) Mg; ether
22. ¾ ¾¾¾¾®
N (2) Ph -CHO
(3) H 3O Å N
| |
H H
The given product can not be obtained in the above reaction. Identify the correct product
obtained.
OH O
|
CH – Ph CH – Ph
(a) (b) (c) (d)
N CH – PhN N N
| | |
H OH CH – Ph
|
OH
23. Which of the following gives two isomers of 3° alcohol, when treated with
phenyl magnesium bromide ?

(a) (b)

O O
D D

(c) (d)

O O
O
Me H
MeMgBr
24. ¾ ¾¾¾® Product of the reaction is :

H Ph
Me Me
Me H Me H
(a) (b) (c) Both (a) and (b) (d) None of these
HO H H OH
Ph Ph
RMgBr
25. ¾® Product; The product of the reaction is :
¾ ¾¾
S
O O
(a) HSO 2 — CH 2 — CH 2 — CH 2 — CH 2 — R
(b)H — SO 2 (CH 2 ) 3 — R

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 (c) (d) H — SO 2 (CH) 3 — R
MgBr
SO2
26. When carboxylic acid reacts with organolithium reagents to give ketones, side reaction
sometimes occur. For example,
CH 3 O
| ||
( x ) CH 3 Li NH 4Cl
HOCH 2CH 2 CH CH 2 CH 2 C OH ¾ ¾¾¾ ¾® ¾ ¾¾ ¾®
tetrahydro furan H2

CH 3 O
| ||
HOCH 2CH 2 CH CH 2 CH 2 - C - CH 3 + compound (B)
Compound A 63% 37%
Value of (x) in above reaction is :
(a) 2 (b) 3 (c) 4 (d) 5
27. Which of the following alcohol can not be prepared by the reaction of acid chloride with
excess of Grignard reagent followed by acidification ?
OH OH OH OH
(a) Ph Ph (b) Ph CH3 (c) Et Et (d) CH3 Et

CH3 CH3 CH3 Ph

(i) MeMgI H +
28. ¾ ¾¾¾ ¾® ( B ) ;
¾® (A) ¾ ¾
(ii) NH 4Cl D
(major)

Product (B) of the above reaction is :

CH2
||
(a) (b)

(c) (d)

29. The reaction of elemental sulphur with Grignard reagent followed by

acidification leads to the formation of
(a) mercaptan (b) sulphoxide
(c) thioether (d) sulphonic acid

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30. + MgBrCH 2 CH 2 CH 2 CH 2 MgBr ¾(i)
¾¾
THF
¾® product; Product of the reaction is :
(ii) H 3O +
O O
O
||
(a) HO — (CH 2 )3 — C — CH 2 — CH 2 — CH 3(b)
HO (CH2)3 — OH

(c) HO CH — CH 2 — CH 3 (d)
|
OH HO CH2 — CH2 — CH3
O OH
|
C — Cl C — CH3
(i) x CH3MgBr |
31.
(ii) H + CH3
C — Cl
C
O OH
Me
Me
Number of moles of CH 3 MgBr consumed in above reaction is :
(a) 2 (b) 4 (c) 6 (d) 8
32. End product of the given reaction is :
Cl
Mg 1.CH O
¾ ¾¾® ( A) ¾ ¾¾2¾® (B)
Et 2O 2. H 3O Å

OH
OH
(a) (b)

OH
(c) (d)

33. Which of the following compound is not a suitable solvent for Grignard reaction ?
O
(a) (b)
O O
(THF) (1, 4-dioxane)

(c) CH 3 — O — CH 2 — CH 2 — O — CH 3 (d)

Br Mg
34. ¾ ¾¾® Predict major product of the reaction :
Et 2O
(2 mole)
(a) (b) (c) (d)
35. Which of the following reaction sequences would be the best for synthesis of t-butyl alcohol ?

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 O
2 H 3O Et O Å
(a) CH 3 CH 2 MgBr + CH2 – CH2 ¾ ¾¾ ® ¾ ¾¾ ¾®
2 CO 3 H OÅ
(b) CH 3 CH 2 CH 2 MgBr ¾ ¾¾ ® ¾ ¾¾ ¾®
Et 2O

O
||
Et 2O H 3O Å
(c) CH 3 MgBr + CH 3 — C — CH 3 ¾ ¾¾ ® ¾ ¾¾ ¾®
O
||
Et 2O H 3O Å
(d) CH 3 CH 2 MgBr + CH 3 — C — H ¾ ¾¾ ® ¾ ¾¾ ¾®
36. What is the major product of the following reaction ?
3 CH MgI 3 H OÅ
CH 3 — C ºº N ¾ ¾¾
Et O
¾® ¾ ¾¾ ¾®
2

H
N

(a) CH 3 — CH 2 — NH — CH 3 (b) CH3 – C – CH3

O O
|| ||
(c) CH 3 — C — CH 3 (d) CH 3 — CH 2 — C — OH

H CH3
(1) PhMgBr
37. C ¾ ¾¾¾¾® Products; Product obtained in this reaction are :
(2) H+
O
(a) diastereomers (b) racemic (c) pure enantiomer (d) meso
38. CH 3 CO 2 Et + (CH 2 ) 5 (MgBr) 2 ¾ ¾¾¾ ® C 7 H 14 O ; compound (A) will be :
+ (2) H
(A)
OH
OH
(a) (b)
OH
O
||
(c) CH 3 — C — (CH 2 ) 4 — CH 3 (d)
O
C – Ph
(1) PhMgBr CuCl
39. ¾ ¾¾¾¾¾¾® ( A) ; A will be :
(2) H+ C19 H 20O

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 OH O O O
| h ||
C –P C – Ph C – Ph C – Ph
|
(a) (b) (c) Ph (d)
Ph
Ph
Ph
MeO OMe
n - Bu 2Cu Li
40. ¾® Product of the reaction will be :
¾ ¾¾¾¾¾¾¾
(n - Bu = n - butyl group)

Br

MeO OMe MeO OMe

(a) (b)

n-Bu n-Bu
OMe Bu OH OH
(c) (d)

Br Br
O
Li ||
Cl -C -O - Me
41. ¾ ¾¾¾¾® (?) ; Product of this reaction is :

Cl CO2Me
(a) (b) (c) (d)

42. Ethyl acetoacetate when reacts with one mole methyl magnesium iodide then product of
reaction will be :
O O OQMgBr O
|| ||
(a) CH 3 — C — CH 2 — C — CH 3 (b) CH3 — C — CH2 — C — CH3

CH3
O O
Q ||
(c) CH3 — C — CH — CO2Et (d) CH -2 — C — CH 2 — CO 2 Et
MgBr
O
||
43. CH 3 MgBr + Et ¾ O ¾ C ¾ O ¾ Et ¾¾® ( A); Product A is :
( excess) (2) H Å

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 OH
O OH
OH
(a) (b) (c) (d)
C 2H 5MgI H 2O H +
44. For the sequence of reactions, A ¾ ¾¾¾ ®B ¾ ¾¾¾® tert-Pentyl alcohol. The
ether
compound A in the sequence is :
(a) 2-Butanone (b) Acetaldehyde (c) Acetone (d) Propanal
O
||
(1) excess CH 3 - Li
45. PhMgBr + CH 3 - CN ¾ ¾¾
¾ ® ( A) Ph - C - O - H ¾ ¾¾¾¾¾¾ ® (A)
Å H 3O (2) H 3O
Same product (A) will form in both reactions. A is :
OH O
| ||
(a) Ph — C — CH 3 (b) Ph — CHO (c) Ph — C — CH 3 (d) Ph — CH 2 — CO 2 H
|
CH 3

46. Which of the following Grignard reagent can be prepared ?

(a) Br — Mg — CH 2 — CH 2 — CH 2 — O — H (b) Br — Mg — CH 2 — CH 2 — SH
(c) BrMg — CH 2 — CH 2 — NH 2 (d) BrMg — CH 2 — CH 2 — N — CH 3
|
47. In the reaction sequence :
CH 3
O

3 (i) CH MgBr CuCl

¾ ¾¾¾¾¾¾® (X), Product (X) will be :
+ (ii) H 2O H

CH3 OH O O CH3
OH
H CH3
(a) (b) (c) (d)
CH3 OH CH3
CH MgBr(excess)
3
48. (C 2 H 5 O) 2 CO ¾ ¾¾¾¾¾
+
¾® A. A (alcohol) can also be obtained by :
H 3O

O
CH 3 MgBr(2mol)
|| CH 3 MgBr(2 mol)
(a) CH 3 CH 2 CHO ¾ ¾¾¾¾¾
¾® (b) CH 3 C OC 2 H 5 ¾ ¾¾¾¾¾ ¾®
H 3O+ H 3O
+

O
||
CH 3 MgBr (1mol)
(c) CH 3 C CH 3 ¾ ¾¾¾¾¾ ¾® (d) as in (b) and (c)
H 3O +

49. The principal product of the reaction between methyl butanoate and 2 moles of CH 3 MgBr
after hydrolysis is :
(a) C 3 H 7 COCH 3 (b) C 3 H 7 C(OH)(CH 3 ) 2
(c) C 3 H 7 CHOHCH 3 (d) C 3 H 7 COCH(CH 3 ) 2

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50. Which of the following compounds will form hydrocarbon on reaction with Grignard reagent ?
(a) CH 3 CH 2 OH (b) CH 3 CHO (c) CH 3 COCH 3 (d) CH 3 CO 2 CH 3
51. What is the product ( B ) of the following reaction sequence ?
Br
Mg
¾ ¾¾® A
Et 2O

O
(1) Et O
2
A + ¾ ¾¾¾ ®B
CH3 (2) H 3O
Å

OH O OH
CH3 CH3
OH CH3
(a) (b) (c) OH (d)
CH3
OH
52. Which, if any, of the following pairs of reagents could be used to prepare 2-phenyl-2-butanol?
O O
|| ||
(a) CH 3 CH 2 MgBr + Ph — C — CH 3 (b) CH 3 CH 2 MgBr + C 6 H 5 CH 2 C H
O O
|| ||
(c) CH 3 MgI + C 6 H 5 CH 2 C CH 3 (d) C 6 H 5 MgCl + CH 3 C CH 2 CH 2 CH 3

53. What is the product of the following reaction?

1. diethyl ether
+ 2CH 3 MgBr ¾ ¾¾¾¾¾® Product
O 2. H 3O +
O
(a) HO – CHC H 2 CH 2 CH 2 CH – OH (b) CH 3OCH 2 CH 2 CH 2 CH 2 CHC H 3
| | |
CH 3 CH 3 OH
CH 3
|
(c) HOCH 2 CH 2 CH 2 CH 2 C — OH (d) HOCH 2 CH 2 CH 2 CH 2 CHO CH 3
| |
CH 3 CH 3

Ph
54. Mg 1. HCHO
; Product (B) is :
A B
ether 2. H+
Br
Ph
(a)
CH2 — OH

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 (b) Ph — C ºº C — CH 2 — CH 2 — CH 2 — OH
(c) Ph — C ºº C — CH 2 — CH 2 — OH
(d) Ph — CH 2 — C ºº C — CH 2 — CH 2 — OH
55. What sequence of steps represents the best synthesis of 4-heptanol (CH 3 CH 2 CH 2 ) 2 CHOH ?
(a) CH 3 CH 2 CH 2 MgBr (2moles) + formaldehyde (H 2 C = O) in diethyl ether followed by
H 3O +
(b) CH 3 CH 2 CH 2 MgBr + butanol (CH 3 CH 2 CH 2 CH = O) in diethyl ether followed by H 3 O +
(c) CH 3 CH 2 CH 2 CH 2 MgBr + acetone [(CH 3 ) 2 C = O] in diethyl ether followed by H 3 O +
(d) (CH 3 CH 2 CH 2 ) 2 CHMgBr + formaldehyde (H 2 C = O) in diethyl ether followed by H 3 O +
O
Et
(1) MeMgBr
56. ¾ ¾¾¾¾® Comment on stereochemistry of products :
(2) NH 4Cl
H Me

(a) diastereomers (b) racemic

(c) single stereoisomer (d) meso
CH2 — OH
|
57. CH —OH + CH 3 MgBr —® xCH 4
| (Excess)
CH2 — SH
What is the value of x in the above reaction ?
(a) 1 (b) 2 (c) 3 (d) 4
58. 0.40 g of an organic compound (A), (M.F.- C 5 H 8 O) reacts with x mole of CH 3 MgBr to
liberate 224 mL of a gas at STP. With excess of H 2 , (A) gives pentan-1-ol. The correct
structure of (A) is :
(a) CH 3 — C ºº C — CH 2 — CH 2 —OH
(b) CH 3 — CH 2 — C ºº C — CH 2 — OH
(c) H — C ºº C — CH 2 — CH 2 — CH 2 — OH
(d) H — C ºº C — CH 2 — CH — CH 3
|
OH O
Br2 ||
Mg CH 3 -C -CH 3 H+
59. CH 3 — CH == CH 2 ¾ ¾¾¾¾® ¾ ¾¾¾
¾® ¾ ¾¾¾¾
NH 4Cl
¾® ¾® ( X )
¾¾
D
hn Dry ether
(low conc.) (major)

End product (X) of the above reaction is :

CH 2
||
(a) CH 2 == CH — CH 2 — C — CH 3

(b) H 2 C == CH —CH == C — CH 3
|
CH 3

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 OH
|
(c) H 2 C == CH — CH 2 —C — CH 3
|
CH 3
(d) H 2 C == CH — CH 2 — CH — CH 2 — OH
|
CH 3
Mg
60. CH2 — CH — CH2 — Br ¾ ¾¾¾¾® ( A) ¾ CH
¾¾ 3I
® ( B ) ; Product (B) is :
dry ethane
O
(a) CH2 — CH — CH2 — CH3
O
(b) CH 3 — O — CH 2 — CH 2 — CH 3
(c) H 2 C == CH — CH 2 — O — CH 3
(d) H2C — CH — CH3
O
61. Compound A was treated with a large excess of CH 3 MgBr . The resulting product was
exposed to POCl 3 pyridine to give compound B , as one of many products :

B
Which of the following compounds can be A ?
O O

H H
(a) (b)

(c) (d)

62. Identify product Z in the following reaction sequence :

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 1. C 6 H 5MgBr,
NaCN diethylether
H 2 C == CHCH 2 Br ¾ ¾¾® Y ¾ ¾¾¾ ¾¾® Z
2. H 3O +

O O
|| ||
(a) H 2 C == CHCH 2 C C 6 H 5 (b) H 2 C == CHCH 2 NHC C 6 H 5
OH NH 2
| |
(c) H 2 C == CHCH 2CH C 6 H 5 (d) H 2 C == CHCH 2 CH C 6 H 5

O O
63. CH3MgBr

Cl

(Consider all steps and intermediate) correct statement is :

(a) Nucleophilic addition (b) Nucleophilic substitution reaction
(c) Product obtained is chiral (d) All
64. Which combination(s) of alkyl bromide and epoxide can be used to prepare the following
product by addition of the Grignard reagent derived from the alkyl bromide to the epoxide ?
OH

Br
O Br O
(a) , (b) ,

O O

(c) (d)

65. What will be the final major product ?

S

RMgX 3 CH - I
¾® (I) ¾ ¾¾
¾ ¾¾ ¾® (II)
O
18
18
S O S O

(a) (b) (c) 18 (d)

18
SH R SH R OCH3 R SCH3 R

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66. Give the expected product of the following reaction.
O
1. MeMgBr (excess)
O
Cl 2. H2O

O OH O OH
(a) (b)
H3CO CH3 HO CH3

CH3 CH3
H3C OH
H3C
(c) O (d)
HO HO CH3

ANSWERS — LEVEL 1
1. (b) 2. (d) 3. (b) 4. (d) 5. (c) 6. (d) 7. (c) 8. (c)

9. (d) 10. (c) 11. (b) 12. (b) 13. (b) 14. (c) 15. (b) 16. (b)

17. (d) 18. (d) 19. (d) 20. (d) 21. (c) 22. (b) 23. (b) 24. (c)

25. (c) 26. (b) 27. (d) 28. (d) 29. (a) 30. (b) 31. (b) 32. (b)

33. (d) 34. (b) 35. (c) 36. (c) 37. (b) 38. (b) 39. (b) 40. (a)

41. (b) 42. (c) 43. (b) 44. (c) 45. (c) 46. (d) 47. (b) 48. (d)

49. (b) 50. (a) 51. (a) 52. (a) 53. (c) 54. (b) 55. (b) 56. (a)

57. (c) 58. (c) 59. (b) 60. (c) 61. (d) 62. (a) 63. (d) 64. (b)

65. (c) 66. (d)

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 Level - 2
1. Comprehension

Grignard reagent is usually prepared by

Et O
R - X + Mg ¾ ¾2¾® RMgX Grignard reagent
Et 2O
Ar - X + Mg ¾ ¾¾® ArMgX Grignard reagent
Grignard reagent acts as a strong base. Grignard reagent carry out nucleophilic attack in
absence of acidic hydrogen. Grignard reagent form complex with its ether solvent.
Complex formation with molecule of ether is an important factor in the formation and
stability of Grignard reagent.

A. What is the correct order of reactivity of halides with magnesium ?

(a) R - Cl > R - Br > R - I (b) R - Br > R - Cl > R - I
(c) R - I > R - Br > R - Cl (d) R - I = R - Br = R - Cl
B. Which of the following will undergo acid-base reaction with Grignard reagent ?
(a) HC º CH (b) R - OH
(c) R - CO 2 H (d) All of these
C. Which of the following reactants give primary alcohol as a major product when reacts with
RMgX followed by acidification ?
O
||
(i) CH — CH (ii) H - C - H (iii) CH2 — CH — CH3
2 2
O O
O
||
(iv) C H 3 - C -H (v) (vi) O
O
(a) i, ii, v (b) i, ii, v, vi (c) ii, iv, vi (d) v, iv, iii, vi
O
||
(1) xRMgX
D. Cl - C -O - Et ¾ ¾¾¾¾® 3° alcohol. Value of x is :
(2) NH 4Cl

(a) 2 (b) 3 (c) 4 (d) 5

O OH
|| |
(1) x PhMgBr
E. H - O - CH 2 - CH 2 - C - O - Et ¾ ¾¾¾¾ ¾® HO - CH 2 - CH 2 - C - Ph, Value of x is :
(2) H + |
Ph
(a) 2 (b) 3 (c) 4 (d) 5

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F. Which of the following Grignard reagents is not possible ?
(a) HS - CH 2 - CH 2 - CH 2 MgBr (b) HO - CH 2 - CH 2 - CH 2 MgBr
(c) NH 2 - CH 2 - CH 2 - CH 2 MgBr (d) All of these
G. How many different Grignard reagents when react with EtOH, give n-butane as product
(excluding stereoisomerism).
(a) 1 (b) 2 (c) 3 (d) 4
2. Match the column I and II. (Matrix)
Column (I) Column (II)
Reactant Product
O
||
(a) (p) Ph – CH 2 – OH
PhMgBr + Cl - C - O - Et ¾ ¾¾ ®
(excess)
ÅH

O
|| Ph - CH - Ph
(b) (q) |
PhMgBr + H - C - O - Et ¾ ¾
¾ ®
(excess)
H
Å OH
OH
O |
|| Ph — C — Ph
(c) (r)
PhMgBr + H - C - H ¾ ¾
¾ ® |
Å H
(excess) Ph
OH
O |
|| Ph — C — Ph
(d) (s) |
PhMgBr + CH 3 - C - O - Et ¾ ¾
¾ ®
Å H
(excess) CH3

3. Match the column I and II. (Matrix)

Column (I) Column (II)
Reaction Reactant
O O
(a) PhMgBr + (A) ¾ ¾¾® 1ºalcohol (p) || ||
HÅ
CH 3 - C - CH 2 - C - CH 3
O
(b) PhMgBr + (B) ¾ ¾¾® 2ºalcohol (q) ||
HÅ
CH 3 - C - CH 3
O
(c) PhMgBr + (C) ¾ H
¾¾Å
® 3ºalcohol (r) ||
CH 3 - C - H
O
(d) PhMgBr + (D) ¾ H
¾¾Å
® (s) ||
H - C -H

Match the missing reactant A, B, C, D

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4. Match the column I and II. (Matrix)

Column (I) Column (II)

Moles of
Reaction
PhMgBr used
O
(a) || (p) 1
PhMgBr + Et - O - C - O - Et ¾ ¾
¾ ® 3ºalcohol
Å H
O
(b) || (q) 2
PhMgBr + HO - CH 2 - C - CH 3 ¾ ¾
¾ ® 3° alcohol
Å H
O
(c) || (r) 3
PhMgBr + CH 3 - C - CH 3 ¾ ¾
¾ ® 3ºalcohol
Å H
O
||
HO C – Cl
(d) (s) 4
PhMgBr + ¾¾
¾ ® 3ºalcohol
Å H
HO

5. When 20 g of a compound (A) (M.F. = C 4 H 10O 4 ) reacts with excess of CH 3 MgBr, 14.6 L of
CH 4 is obtained at STP. What is structural formula of (A) ?
CH2— OH CH 2 OH
| |
(a) (CH — OH) 2 (b) HO — CH 2 — C — CH 2 OH
| |
CH2— OH OH
HO OH

(c) (d) Both (a) & (b)

HO OH

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 Subjective Problems
1.

H MgBr r r
excess H H
OH O D
(X)

How many geometrical isomer of (X) is possible ?

2. How many isomer of C 4 H 8 O when reacts with CH 3 MgBr followed by acidification to give 2º
alcohol (only consider carbonyl isomers)?
(including stereoisomer)
3.
Total number of RMgX are consumed in the following reaction

Cl

O CººN
x RMgX
O
O

4. How many isomers of C 4 H 10 O reacts with CH 3 MgBr to evolve CH 4 gas ? ( Excluding

stereoisomer)
5. How many carbonyl isomers of C 5 H 10 O which reacts with PhMgBr to give racemic mixture ?
6. How many moles of Grignard reagent will consume when it reacts with following
compound?
CH==O O

HO C—Cl

H—S C—O—Et
C O
N

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 ANSWERS — LEVEL 2

1. A – c; B – d; C – a; D – b; E – b; F – d; G – b
2. a – r; b – q; c – p; d – s
3. a – s; b – r; c – q; d – p
4. a – r; b – q; c – p; d – s
5. (d)

Subjective Problems
1. 4 2. 2 3. 7 4. 4 5. 5 6. 8

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