ORGANIC CHEMISTRY

TARGET IIT-ENTRANCE 2013

XII

GRIGNARD REAGENT HOH or ROH

2
or Ph–OH

2 NH H

O2 ,H2 O
CdC te d
N
SO2,H

l i mi
or R 3 or R


2 O,
CS

l2
H
O lim gBr
NH

S,H
2 ,H


H2 ite 2

X

O, d

R–
CH SiCl
CO H
2 ,H  O limit 4 CH 2
RCHO,H2 ed –CH=
ClCH 2
O R–Mg–X R–Mg–X
Me–CH-CH2, RCOR,H2O PbCl2 ClCH2 OR
limited
H2O Ph
O HCO
H2 Cl 2 CH
O H 2, OEt Zn ted
3O 

2C
HC (

-C i l

Cl–
lim
eq.) 2 O

CH 2
OO ½ e
H

RCO

CN
(½ Et,H
N,

2
Et q.)

Cl
RC

,H 2

I2
OEt

Br2
OO

O
RC

?
Hydrocarbon part of Grignard reagent (R–Mg+X–) has some carbanionic characters. So, it could
act as a base as well as nucleophile both. As a nucleophile, it could show Nucleophilic substitution,
Nucleophilic addition and Nucleophilic Addition-Elimination reactions.

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 EXERCISE - I
Q.1 Consider the given organometallic compound.
(I) (CH3)2Hg (II) (CH3)2Zn (III) (CH3)2Mg (IV) CH3Li
The correct decreasing order of ionic character is
(A) I > II > III > IV (B) II > I > III > IV (C) I > III > II > IV (D) IV > III > II > I

Q.2 The order of reactivity of alkyl halide in the reaction R–X + Mg  RMgX is
(A) RI > RBr > RCl (B) RCl > RBr > RI
(C) RBr > RCl > RI (D) RBr > RI> RCl

MgBr OH

Q.3 +  A

O – Ph

(A) (B) (C) (D)

NBS D O
Q.4 14CH =CH–CH
2 3  Mg
 /
ether
 2 Product(s)
CCl4 / Peroxide

Product(s) is / are:
(A) 14CH2= CH–CH2–D (B) CH2 = CH– 14CH2–D
(C) Both of these (D) None of these

Q.5 On conversion into Grignard followed by treatment with ethanol, how many alkyl halides (excluding
stereoisomers) would yield 2-methyl butane.
(A) 2 (B) 3 (C) 4 (D) 5

(2)
O OH
C
O (3)
H
H
Q.6 S
(1) RMgX
 (2 moles )
 
C


CH
(4)
Deprotonation will occur from the following positions:
(A) 1,2 (B) 1,3 (C) any two positions (D) 1,4

Q.7 How many litres of methane would be produced when 0.595 g of CH3MgBr is treated with excess of
C4H9NH2
(A) 0.8 litre (B) 0.08 litre (C) 0.112 litre (D) 1.12 litre

Q.8 How many litres of ethene would be produced when 2.62 g of vinyl magnesium bromide is treated with
224 ml of ethyne at STP.
(A) 0.224 litre (B) 0.08 litre (C) 0.448 litre (D) 1.12 litre
Grignard Reagent [2]
 D O
Q.9 1
equivalent Mg
  X 
2
 Y; Y is
ether

(A) (B) (C) (D) None of these

Q.10 Br–CH2–CC–CH2–Br Mg

 BrMg–CH2–CC–CH2–MgBr
( excess)
Et 2O

Product
The major product is:
(A) Br–Mg–CH2–CC–CH2–Br (B) Cyclobutyne
(C) —(CH 2  C  C  CH 2—
)n (D) CH2 = C=C=CH2

CH3MgX
Q.11 O
NH4Cl
Product is
(A) Enantiomer (B) Diastereisomer (C) Meso (D) Achiral

Q.12 CH3—CH—CH2 CH

3MgCl

H 2O
O
(A) CH 3  CH  CH 2 OH (B) CH 3  CH  CH 2  CH 3
| |
CH 3 OH
(C) CH 3  CH  CH 3 (D) HO – CH2 – CH2 – CH2 – CH2 – OH
|
CH 3

r1
Q.13 (i) + Ph Mg Br  Ph CH2 CH2 OH
O

r2
(ii) + Ph Mg Br  Ph CH2 CH2 CH2 OH
O
(A) r2 > r1 (B) r1 > r2 (C) r1 = r2 (D) r1 = 2r2

Q.14 What will be the order of reactivity of the following carbonyl compounds with Grignard's reagent?
H H CH3 Me3C
(I) C = O (II) C=O (III) C=O (IV) C=O
H CH3 CH3 Me3C
(A) I > II > III > IV (B) IV > III > II > I
(C) II > I > IV > III (D) III > II > I > IV

Grignard Reagent [3]

 OH
Q.15 Carbonyl compound (X) + Grignard reagent (Y) Me Ph
Et
X , Y will be
O O
|| ||
(A) Et  C  Ph , Me Mg Br (B) Me  C  Ph , Et Mg Br
O O
|| ||
(C) Me  C  Et , Ph Mg Br (D) Et  C  Ph , Et Mg Br

Q.16 Order of rate of reaction of following compound with phenyl magnesium bromide is:
O O O
|| || ||
Me  C  Cl Me  C  H Me  C  O  Et
I II III
(A) I > II > III (B) II > III > I (C) III > I > II (D) II > I > III

Q.17 Select the correct order of decreasing reactivity of the following compounds towards the attack of
Grignard reagent
(I) Methyl benzoate (II) Benzaldehyde (III) Benzoylchloride (IV) Acetophenone
(A) II > III > I > IV (B) III > IV > II > I
(C) III > II > IV > I (D) II > IV > I > III

Q.18 Which of the following reacts faster with RMgX.

O O O O
|| || || ||
(A) R  C  Br (B) R  C  H (C) R  C  OEt (D) R  C  NH 2

Q.19 Select the correct order of reactivity towards Grignard reagent for nucleophilic attack.
O O
|| ||
(A) R  C  R > R  C  H
(B) Cl  CH 2  C  H > CH 3CH 2  C  H
|| ||
O O

O O
|| ||
(C) CH 3  C  O NO2 < CH 3  C  O

O O
|| ||
(D) R  C  OR > R  C  NR 2

Grignard Reagent [4]

Q.20 The reaction of 1 mole each of p-hydroxy acetophenone and methyl magnesium iodide will give
O O
(A) CH4 + IMgO C—CH3 (B) CH3–O C—CH3

OMgI MgI
O
(C) CH3–C OH (D) CH3O C—CH3
CH3
CH MgBr
Q.21 CH 3CCH 2 CH 2 CH 2Cl 3 A, A is

||
O
CH 3
|
(A) CH 3CCH 2 CH 2 CH 2 Cl (B) CH 3CCH 2 CH 2 CH 2 CH 3
| ||
OH O

(C) (D)

HO OEt
2 CH3MgX
Q.22 NH4Cl
P1 + P2

Identify P1 & P2.

O HO Me

(A) CH4 (B) (C) (D)

O

Q.23 (R) - 2-Bromooctane (

i ) Mg
 X
( ii ) CO 2
( iii ) H 

X is

(A) (B)

(C) A and B both (D) None of these

Q.24 In which one of the following reaction products are not correctly matched in
(i) CO2
(A) RMgX + CO2 Carboxylic acid
(ii) H
(B) RMgX + C2H5OH  Alkane
(C) RMgX + CH3CH2Cl  Alkene
(D) RMgX + Cl O  Ether

Grignard Reagent [5]

 Br
14
NaHCO
Q.25 Mg
 (A) (
i ) CO 2
 (B)  3  (C) gas
( ii ) H  / H 2 O
Product C is
(A) CO (B) 14CO2
(C) CO2 (D) A mixture of 14CO and CO
2 2
OEt
Q.26 MgBr + H – C OEt followed
  product.
OEt H 3O 
Ethyl ortho formate

O
||
(A) C  CH3 (B) CH2CH=O

(C) CH = O (D) CH  CH 3
|
CH  O

Q.27 Which reaction gives 1° aromatic amine as major product.

(A) Mg
 /
ether
 NH
3  (B) Mg
 /
ether
 NH
3 

(C) Mg
 /
ether
 NH
3  (D) Hg
(OAc ) 2

Ph NH 3 / NaBH 4

O
||
CH 3 CCH3 
Mg H
Q.28 CH3–CH=CH2 Br
2      
 Dry ether NH 4Cl 
End product of above reaction is
CH 2
||
(A) CH 2  CH  CH 2  C  CH 3 (B) H 2C  CH  CH  C  CH 3
|
CH 3
OH
|
(C) H 2C  CH  CH 2  C  CH 3 (D) H 2C  CH  CH 2  CH  CH 2  OH
| |
CH 3 CH 3
Br
1. Mg / ether
Q.29        Product (s)

2. CH 3CHCH 2CH 3. H 3O
| ||
OH O
Select the product from the following

I: II : CH 3CHCH 2CH III :

| ||
OH O
(A) III (B) I, III (C) I, II (D) II, III

Grignard Reagent [6]

Q.30
( i ) CH CN
RMgX  3   (A) ( i ) RMgX
 (B) will be
( ii ) H 3O  ( ii ) aq. NH4Cl
(A) 1° ROH (B) 2° ROH (C) 3° ROH (D) Alkene
O
||
Q.31 C 2 H 5O  C  OC 2 H 5 2
CH 3MgBr
  A. Product A formed
(A) is ethyl acetate
(B) further react with CH3MgBr/H2O+ to give acetone
(C) further react with CH3MgBr/H2O+ to give t-butyl alcohol
(D) Can give pinacol when treated with Mg followed by H2O

Q.32 Which of the following is incorrect.

O
O
C ||
CH 3MgX
(A) Cl OC2H5     CH 3  C  OC2 H 5
(1 eq )

O
OC2H5 ||
C 2 H 5 MgX
(B) CH3–C OC2H5    CH 3  C  OC 2 H 5
(1 eq )
OC2H5
S S
||  ||
(C) CH3MgX + C = S H
3O
 CH 3  C  SH
O O
||  ||
(D) CH3MgX + C = O H
3O
 CH 3  C  OH
O
Q.33 MgBr + H–C–Cl  product.

O
||
(A) C  CH3 (B) CH2CH=O

(C) CH = O (D) CH  CH 3
|
CH  O
O O
|| ||
Q.34 CH 3CCH 2 CH 2 COCH 2 CH 3 (
i ) CH 3MgBr ( one mol )
     A, A formed in this reaction is
(ii ) H 3O 

OH O O O
| || || ||
(A) CH 3CCH 2 CH 2COCH 2CH 3 (B) CH 3CCH 2 CH 2CCH 3
|
CH 3
CH 3 CH 3
| |
(C) (D) CH 3CCH 2 CH 2 CCH 3
| |
OH OH
Grignard Reagent [7]
 CH MgBr (1 eq.)
Q.35 3   ?

The product is:

(A) (B) (C) (D)

Q.36 CH2 = C = O (

i ) Br2
 C4H8O
( ii ) CH 3MgBr
( 2 equi )

(A) (B) (C) (D) All of these

( i ) CH CN (i ) RMgX
Q.37 RMgX  3  (A) ( ii )
  (B) will be
aq. NH4Cl
(ii ) aq. NH 4 Cl

(A) 1° ROH (B) 2° ROH (C) 3° ROH (D) Alkene

r1
Q.38 (i) + Ph Mg Br  Ph CH2 CH2 OH
O

r2
(ii) + Ph Mg Br  Ph CH2 CH2 CH2 OH
O
(A) r2 > r1 (B) r1 > r2 (C) r1 = r2 (D) r1 = 2r2

Q.39 Compounds are shown with the no. of RMgX required for complete reaction, select the incorrect option
(A) CH3COOC2H5 1
(B) CH3COCl 2
(C) HOCH2COOC2H5 3

(D) 4

Q.40 The number of moles of grignard reagent consumed per mole of the compound
is:

(A) 4 (B) 2 (C) 3 (D) 1

Grignard Reagent [8]

Q.41 Which of the following reacts with 4 moles of RMgX.

COCl CH2–Cl
ROC
(A) (B)
CHO COOEt
OH

COCH
EtO OCH3
O
O
(C) O (D) RN
H O
Et

Q.42 How many moles of Grignard reagent will be required by one mole of given compound?
O
SH
HO C – OEt

C – Cl
CH2–CH2 O
Cl
(A) 7 (B) 6 (C) 8 (D) 5

For Q. No.43 to Q. No. 45

Consider the given reaction and answer the following questions
COOCH3

MeMgBr
  Products
O OCH3 ( excess )
O SH
||
O

Q.43 No. of RMgX consumed in the reaction is

(A) 4 (B) 5 (C) 6 (D) 7

Q.44 How many product will be fromed in given reaction (excluding stereo)
(A) 2 (B) 3 (C) 4 (D) 5

Q.45 Which of the following reaction will give the same Hydrocarbon formed as one of the product in the
above reaction.
(A) EtMgBr + Me – OH  (B) PhMgBr + Me – OH 
(C) MeMgBr + Ph – OH  (D) MeMgBr + CH3 – CHO 

Grignard Reagent [9]

 O
||
Q.46 CH2=CH C  H (
i ) CH 3MgBr / CuCl
    Product (1, 4 addition). It is
( ii ) H 3O 

OH
|
(A) CH 2  CH  C H (B) CH 2 CH  CH  CH 3
| |
CH 3 OH
(C) CH3CH2CH2CHO (D) none

Q.47 In the reaction sequence:

(i ) CH MgBr / CuCl
 3    (X) Major + (Y)
(ii ) H 2O / H 

(X) & (Y) respectively are

OH CH3 OH
(A) , (B) ,
CH3

(C) , (D) ,

O (i) CH 3MgBr
|| + P
(ii) H3O
Q.48 CH3CH = CH  C  CH 3
(i) CuI,CH3MgBr
+ Q
(ii) H3O

OH OH
| |
(A) P is CH3CH = CH  C  Me Q is CH3CH = CH  C  Me
| |
Me Me

O OH
|| |
(B) P is CH 3CH  CH 2  C  CH 3 Q is CH3CH = CH  C  Me
| |
CH 3 Me

(C) P is CH 3CH  CH  C(CH 3 ) 2 Q is (CH 3 ) 2 CHCH 2C  CH 3

| ||
OH O

(D) P is (CH 3 ) 2 CHCH 2C  CH 3 Q is CH 3CH  CH  C(CH 3 ) 2

|| |
O OH

Grignard Reagent [10]

 EXERCISE - II

Q.1 Which of the following reacts with Grignard reagent to give alkane?
(A) nitro ethane (B) acetyl acetone
(C) acetaldehyde (D) acetone

Q.2 Nucleophilic addition of Grignard reagent cannot occur in

O O O O
|| | | || ||
(A) CH 3  C  C  CH 3 (B) CH 3  C  CH 2  C  CH 3

O O
|| || O
(C) CH 3  C  CH 2  CH 2  C  CH 3 (D)
O
CH 3
|
conc. H SO NBS ( CH 3 CH ) 2 CuLi
Q.3 H 3C  CH 2  CH 2  CH 2  24  X + Y         Product(s)
|  CCl4 / peroxide
OH
Product(s) are:
CH 3
|
(A) (B) H 3C  CH  CH  CH  CH 2
|
CH 3

(C) H 3C  CH  CH 2  CH  CH  CH 3 (D) H 3C  CH  CH  CH  CH 2  CH 3
| |
CH 3 CH 3

Q.4 Select the correct statement:

(A) 1,4-dibromobutane react with excess of magnesium in ether to generate di-Grignard reagent.
(B) 1,2-dichlorocyclohexane treated with excess of Mg in ether produces cyclohexene.
(C) Vicinal dihalides undergo dehalogenation to give alkene when heated with Zn dust or Mg.
(D) 1,3-dichloropropane by treatment with Zn dust or Mg forms cyclopropane.

O OH

Q.5 (
i ) CH 3MgBr
  (A)
( ii ) H  / H 2O

CH3
(A) The product is optically active
(B) The product contains plane of symmetry
(C) The product shows geometrical isomerism.
(D) The product shows optical isomerism.

Grignard Reagent [11]

 3 ( i ) CH ONH
Q.6 2CH 3MgBr    2 

(ii ) H

(A) CH3–O–NH–CH3 (B) CH3–NH–CH3

(C) CH3–NH2 (D) CH3–OH

Q.7 Select the correct order of reactivity towards Grignard reagent for nucleophilic attack.
O O
|| ||
(A) R  C  R > R  C H
(B) Cl  CH 2  C  H > CH 3CH 2  C  H
|| ||
O O

O O
|| ||
(C) CH 3  C  O NO2 < CH 3  C  O

O O
|| ||
(D) R  C  OR > R  C  NR 2

Q.8 (
i ) PhMgBr
  Product.
( ii ) NH 4Cl

Me
Products in this reaction will be
(A) Stereoisomers (B) Enantiomer (C) Diastereomers (D) Geometrical isomers
OH
Q.9 Carbonyl compound (X) + Grignard reagent (Y) Me Ph
Et
X , Y will be
O O
|| ||
(A) Et  C  Ph , Me Mg Br (B) Me  C  Ph , Et Mg Br
O O
|| ||
(C) Me  C  Et , Ph Mg Br (D) Et  C  Ph , Et Mg Br

O
||
Q.10 C 2 H 5O  C  OC 2 H 5 2
CH 3MgBr
  A. Product A formed
(A) is ethyl acetate
(B) further react with CH3MgBr/H2O+ to give acetone
(C) further react with CH3MgBr/H2O+ to give t-butyl alcohol
(D) Can give pinacol when treated with Mg followed by H2O

Grignard Reagent [12]

Q.11 In which of the following reactions 3°alcohol will be obtained as a product.
O
||
(A) MgBr (excess) + H  C  Cl  

H

O
||
(B) PhMgBr (excess) + CH 3  C  Cl  

H

O O
|| ||
(C) CH3MgBr (excess) + CH 3  C  O  C  CH 3  

H

O
||
(D) CH3MgBr (excess) + Cl  C  O  Et  

H

Cl2 Mg 3 CH CHO
Q.12 PhCH3  (A)  (B)    (C)
h ether NH4 Cl
CH3
OH
| OH CH3 OH
CH2 – CH – CH3 CH3 |
CH – CH3 C – CH3
(A) (B) (C) (D)
CH CH3
HO CH3

Grignard Reagent [13]

 EXERCISE-III
Q.1 X (
i ) CH 3MgBr
  Z
(ii ) HOH
What can be used as X if Z is
(i) CH3 – CH3 (ii) CH3–CH2–OH
(iii) CH 3  CH  CH 3 (iv) CH3–CH2–CH2–OH
|
OH

OH

(v) CH2= CH–CH2–CH3 (vi)

Q.2 4.6 g of a polyhydric alcohol was treated with an excess of methy magnesium bromide to produce 3.36
litre of CH4 at STP. Calculate number of –OH group present in the alcohol.
(molecular weight of alcohol = 92)

Q.3 Calculate number of molecules of Grignard regent consumed by 1 molecule of following

compound.
H

O
O O
O

HO NO2

Q.4 Number of RMgX consumed per molecule with the following reactant.
(a) PhCHO
O O
|| ||
(b) Cl — C — C — OEt
CH2Cl
OH

(c)
CH3O
COCH3
(d) SiCl4

Grignard Reagent [14]

Q.5 (reaction-1)
( i ) x CH MgBr
3
   

( ii ) H3O

( i ) y CH MgBr
3 (reaction-2)
   


( ii ) H3O

O OH
|| | (reaction-3)
Et  O  C  O  Et (
i ) z PhMgBr
  Ph  C  Ph
(ii ) H  |
Ph
What is the value of x + y + z = ?

Q.6 How many cycloalkyl chloride (without considering stereoisomers) would yield
1,3-dimethyl-cyclohexane on conversion into the Grignard reagent followed by treatment with ethanol.

Q.7 How many grams of benzene would be produced when 135.5 gms of phenyl magnesium chloride is
treated with 224 ml of ethyne at STP?

Q.8 Addition of phenyl magnesium bromide to 4-tert-butyl cyclohexanone gives two isomeric tertiary alcohol
as product. Both alcohol yield same alkene when subjected to acid-catalyzed dehydration. Suggest a
reasonable structure for these two alcohol.

4-tert-butyl cyclohexanone

Q.9 Organic halide having carbonyl, cyanide , epoxy , OH , – NH2 , – NHR , –CO2H , –SO3H , –SH ,
– CCH group cannot be used to prepare grignard reagent. Explain why?

Q.10 What is the product in the following reactions.

(a) CH
3MgBr
 A


(b) PhMgBr + CH 2  C  CH 2 
 B
| |
Br Br
(c) CH 2  (CH 2 ) 3  CH 2  CHO (
i ) Mg / ether
  C
| ( ii ) NH 4 Cl
Br

Grignard Reagent [15]

Q.11 Neither of these methods of making pentan-1,4 diol will work. Explain why not – what will happen
instead?
(i) CHO–CH2–CH2–CH2–OH MeMgBr
  CH 3  CH  CH 2  CH 2  CH 2
followed by H  | |
OH OH
CH CHO
(ii) Br–CH2–CH2–CH2–OH Mg
 MgBr–CH2–CH2–CH2–OH 3

Et 2O followed by H

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

Q.12 Conversion : HCCH  CH3–CCD

Ph–Br  Ph–D

Q.13 (a) Unlike other esters which react with Grignard reagents to give tertiary alcohols, ethyl formate
O
||
(HCOCH 2 CH 3 ) yields a different class of alcohols on treatment with Grignard reagents. What kind of
alcohol is formed in this case and why?
O
||
(b) Diethyl carbonate (CH 3CH 2 OCOCH 2 CH 3 ) reacts with excess Grignard reagent to yield alcohols of a
particular type. What is the structural feature that characterizes alcohols prepared in this way?

Q.14 What are the products ?

(a) PhMgBr ( i ) COCl 2

 
(excess) ( ii ) NH 4Cl

O
(b) HS + PhMgBr 
H

Q.15 What products would be formed in these reactions ?

(i ) EtMgBr (i ) CO 2
(a) Ph – C  CH (   A
ii ) Ph CO
(b) Br + Mg dry
 A    B.
2 ether 
( ii ) H 3O
(iii ) NH 4Cl

EtMgBr
(1 eq.)
(c) A. (d)  C11H18O2
 
then H  , H 2O

Grignard Reagent [16]

 EXERCISE–IV
Q.1 Write the structural formula of main organic product formed when ethyl acetate is treated with double the
molar quantity of methyl magnesium bromide and the reaction mxiture is poured into water.
[JEE 1981]
Q.2 Identify the major product. [JEE 1993]
C6H5COOH + CH3MgI  ? + ?
Q.3 Predict the major product. [JEE 1994]
( i ) CH MgBr ( excess )
C6H5– CH2COCH3  3    
(ii ) H

Q.4 Which of the following is an organometallic compound? [JEE 1997]

(A) Lithium methoxide (B) Lithium acetate
(C) Lithiumdimethylamide (D) Methyl lithium
Q.5 (CH3)3CMgCl on treatment with D2O produces [JEE 1997]
(A) (CH3)3CD (B) (CH3)3COD (C) (CD)3CD (D) (CD)3COD
CH MgBr
3
Q.6 Ethyl ester   P, the product 'P' will be
( excess )
[JEE 2003]

(A) (B)

(C) (D)

Q.7 Order of rate of reaction of following compounds with phenyl magnesium bromide is: [JEE 2004]
Ph  C  Ph Me  C  H Me  C  Me
|| || ||
O O O
( I) ( II) ( III)
(A) I > II > III (B) II > III > I (C) III > I > II (D) II > I > III
CH 3
|
Q.8 Ph – MgBr + CH3  C  OH  A [JEE 2005]
|
CH 3

CH 3 CH 3
| |
(A) (B) CH 3  C  OPh (C) (D) CH 3  C  Ph
| |
CH 3 CH 3
Q.9 Identify the reaction mechanism : [(II-7-b)JEE 2011]

Grignard Reagent [17]

 ANSWER KEY

EXERCISE - I
Q.1 D Q.2 A Q.3 A Q.4 C Q.5 C Q.6 A Q.7 C
Q.8 C Q.9 D Q.10 D Q.11 A Q.12 B Q.13 B Q.14 A
Q.15 ABC Q.16 A Q.17 C Q.18 D Q.19 BD Q.20 A Q.21 C
Q.22 AB Q.23 C Q.24 C Q.25 C Q.26 C Q.27 B Q.28 B
Q.29 C Q.30 C Q.31 CD Q.32 B Q.33 C Q.34 C Q.35 D
Q.36 A Q.37 C Q.38 B Q.39 A Q.40 A Q.41 D Q.42 A
Q.43 C Q.44 C Q.45 C Q.46 A Q.47 B Q.48 C

EXERCISE - II
Q.1 AB Q.2 BD Q.3 BC Q.4 ACD Q.5 BC
Q.6 CD Q.7 BD Q.8 ACD Q.9 ABC Q.10 CD
Q.11 BCD Q.12 ABC

EXERCISE-III
Q.1 (i) CH3–Cl (ii) H  C  H (iii) CH 3  C  H (iv)
|| ||
O O
O
CH3
C=O

(v) CH2=CH–CH2–Cl (vi)

Q.2 3 Q.3 5 Q.4 1434 Q.5 12 Q.6 5

Q.7 1.56 gms Q.8 Geometrical isomer will formed Q.9 Not required

Q.10 (a) + CH4 + MgBr

(b) CH 2  C  CH 2 

| |
Ph Br

(c) (
i ) Mg / Ether
 
(ii ) NH 4Cl

Q.11 Due to acidic hydrogen

 
LiO or Na  CH 3Cl   CH 3MgBr
Q.12 (a)HCC–H   H  C  CNa   H  C  C  CH 3    
 BrMg–CC–
liq.( NH ) 3
CH3
D–CC-CH3
D 2O
(b) Ph–Br Mg
 Ph–MgBr  Ph–D

Q.13 (a) Formate gives aldehydes & other esters gives ketones.

Grignard Reagent [18]

 — 2 H O
(b) 3
MgX
 R3C– O MgX 
  R3C – OH + Mg

 2 RO

Q.14 (a) Ph3C–OH (b) PhH

OH
|
Q.15 (a) EtH + Ph 2 C  C  C  Ph (b)

(c)  (d)

EXERCISE–IV
O
||
H O
Q.1 CH 3  C  OC 2 H 5  2CH 3MgBr  
2


OH
|
C6 H 5  CH 2 — C — CH 3
Q.2 C6H5COO¯ Mg I + CH4 Q.3 |
CH 3
Q.4 D Q.5 A Q.6 A Q.7 B Q.8 A
Q.9 Nucleophilic substitution & Nucleophilic addition

Grignard Reagent [19]