Exercise 1

GRIGNARD REAGENT Page # 15
Exercise - I (Only one option is correct)
Q.1 C6H5COOH + CH3MgI  ?

(A) C6H5COOMgI (B) CH4 CH3
(C) Both A & B (D) None (C) CH3 – CH2 – C – OEt (D) Cl – CH2 – C – CH3
O OH
Br
Mg
ether Q.6 2CH2 = CH – CH2 – Cl X
Q.2 + Mg Ether
Y (CH2=CH – CH2)2CH – OH
F MgBr + CH3–CH2–OH
Br F MgBr In the above chemical reaction, Y may be
(A) Ethyl formate
(B) Methyl formate
(A) (B) (C) (D)
(C) Isopropyl methanoate
F (D) Ethanolychloride
Q.3 The reactivity order of CH3MgBr with the following

CH2–CH2–I
compounds is:
OH CH2 – C – Cl
CH3 CH3 O (i) Mg/Ether
Q.7 Product
C
(I) (II)
O F
CH3 C Cl The final product of the reaction is
(III) CH3 – Cl (IV) CH2–CH2–MgI
O CH2–CH2–MgI
(A) I > IV > II > III (B) II > I > IV > III CH2 – C – Cl CH2 – C – Cl
(C) I > II > IV > III (D) IV > II > I > III O
O
(A) (B)
(i) Et2O
Q.4 CH3 – CH – CH2 + (CH3)2CHMgBr (ii)H2O F MgF
O O O
(A) CH3–(CH2)4–CH2– OH
(B) CH3 – CH = CH – CH – CH3
CH3 (C) (D)
CH3 MgF F
(C) CH3 – CH – CH2 – CH
Q.8 Analyse the following reaction
CH3
OH HOCH2CH2COCH2CH2CO2Et 1 CH3MgX P
(D) CH3 – CH – CH 2 – CH3 1 CH3MgX
Q R 1 CH3MgX
CH( CH3)2 if
a is EtO – C – CH2 – CH2 – C – CH2 – CH2OMgX
O O
Followed CH3
Q.5 Cl – CH2 – C – OEt + 2CH3MgI
by H2O
Product O b : EtO – C – CH 2 – CH 2 – C – CH 2 – CH 2OMgX
What is the product O OMgX
CH3 CH3 c : is CH3 – C – CH2 – CH2 – C – CH2 – CH2OMgX
(A) HO – CH2 – C – CH3 (B) Cl – CH2 – C – OEt O O
OH OH
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Page # 16 GRIGNARD REAGENT
CH3
d : is CH3 – C – CH2 – CH2 – C – CH2 – CH2OMgX OH O
OMgX O
Which is incorrect O
(A) P is a (B) Q is c (A) O (B)
(C) R is not d (D) Q is b O
Q.9 Match List –I & List – II and select the correct

code
OH
List – I
H3O (C) (D) All of these
(a) RMgX + HCHO  adduct
O
n-carbon
H3O
(b) RMgX + (CH2)2O  adduct
Q.12 The reaction
n-carbon
BrCH2CH2CH2Br + Mg Et2O
H3O
(c) RMgX + CO2  adduct Product mainly
n-carbon (A) CH3CH2CH3 (B) BrMgCH2CH2CH2MgBr
H3O
(d) RMgX + Ph – C  N  adduct
n-carbon (C) (D) CH3CH=CH2
List – II
(i) Ketone Q.13 The order of reactivity of alkyl halide in the
(ii) 1ºAlcohol (n+1) carbon reaction R–X + Mg  RMgX is
(iii) acid (n+1) carbon (A) RI > RBr > RCl (B) RCl > RBr > RI
(iv) 1ºAlcohol (n+1) carbon (C) RBr > RCl > RI (D) RBr > RI > RCl
Code i ii iii iv
A a d b c Mg
B d a c b Q.14 Br–CH2–C  C–CH2–Br BrMg–CH2–C
(excess)
C d b a c Et2O
D b a c d  C–CH2–MgBr
Q.10 Match List –I & List – II and select the correct Mg(1 eq.)
Product
code Et2O
List – I List – II The major product is :
(a) RMgI + Acetonitrile (CH3CN) (i) Alkanone (A) Br–Mg–CH2–C=C–CH2–Br
(b) RMgI + carbon disulphide (ii) Ester (B) Cyclobutyne
(c) RMgI + Ethyl chloroformate (iii) 1ºAlcohol (C) –(CH2–C=C–CH2)n
(d) RMgI + Oxirane (iv) Dithionic acid (D) CH2=C=C=CH2
Code i ii iii iv Q.15 One conversion into Grignard followed by

treatment with ethanol, how many alkyl halides
A c b a d
(excluding stereoisomers) would yeild 2-methyl
B a d b c
butane.
C c d b a (A) 2 (B) 3 (C) 4 (D) 5
D a c d b
Q.16 How many litres of methane would be pro-
O duced when 0.595 g of CH3MgBr is treated
with excess of C4H9NH2
(A) 0.8 litre (B) 0.08 litre
1 mole CH3–Mg–X (C) 0.112 litre (D) 1.12 litre
+ H2O
O
Q.11 Q.17 How many litres of ethene would be produced
O 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
The product is (C) 0.448 litre (D) 1.12 litre
MgBr OH C6H13 C6H13

* *
Q.18 + A (A) CH3 COOH (B) HOOC CH3
H H
(C) A and B both (D) None of these
(A) (B)
Q.23 In which one of the following reaction prod-
OH O–Ph ucts are not correctly matched in
(A) RMgX + CO2 + Carboxylic acid
(2)H
(C) (D) (B) RMgX + C2H5OH Alkane
(C) RMgX + CH3CH2Cl Alkene
(D) RMgX + Cl O Ether
Cl
1 equivalent Mg D2O Q.24 The number of moles of grignard reagent
Q.19 X Y;Y
ether consumed per mole of the compound
Br
HO COOEt is
is
Cl D O
(A) 4 (B) 2 (C) 3 (D) 1
(A) (B)
D Br Q.25 Select the correct statement :
D (A) 1,4-dibromobutane react with excess of
magnesium in ether to generate di-Grignard
(C) (D) None of these
reagent.
D
(B) 1,2-dichlorocyclohexane treated
(C) Vicinal dihalides undergo dehalogenation to
Q.20 Compounds are shown with the no. of RMgX give alkene when heated with Zn dust or Mg.
required for complete reaction, select the (D) 1,3-dichloropropane by treatement with Zn
incorrect option dust or Mg forms cyclopropane.
(A) CH3COOC2H5 1 (B) CH3COCl 2
OH Br2 Mg
Q.26 CH3 – CH = CH2
Dry ether
(C) HOCH2COOC2H5 3 (D) 4 O

+
CH3–C–CH3 H
CHO (X) (Major)
NH4Cl
COOC2H5
End product of above reaction is :
CH2
Q.21 What will be the order of reactivity of the
following carbonyl compounds with Grignard’s (A) CH2 = CH – CH2 – C – CH3
reagent
(B) CH2 = CH – CH = C – CH3
H H
(I) C=O (II) C=O CH3
H CH3
OH
CH3 Me3C
(III) C = O (IV) C=O (C) CH2 = CH – CH2 – C – CH3
CH3 Me3C
(A) I > II > III > IV (B) IV > III > II > I CH3
(C) II > I > IV > III (D) III > II > I > IV (D) CH2 = CH – CH2 – CH – CH2 – OH
CH3
(i) Mg
Q.22 (R) - 2-Bromooctane X is
(ii) CO2 OEt
Followed
(iii)H+ .27 MgBr + H – C OEt +
H3O
OEt
Product CH3
Ethyl ortho formate
(A) CH3 – C – CH2 – CH2 – CH2 – Cl
O
OH
(A) C – CH3 (B) CH2CH=O (B) CH3 – C – CH2 – CH2 – CH2 – CH3
O
H 3C CH3
(C) CH=O (D) CH – CH3 CH3
(C) (D) O
CH=O O CH3 H 3C
Br Q.33
1.Mg/ether O O
Q.28 + Product(s) (i)CH3MgBr(one mol)
2.CH3CHCH2CH 3.H3O CH3 – C – CH2 – CH2 – COCH2 – CH3 +
(ii) H 3O
OH O A, A formed in this reaction is :
Select the product from the following OH O
(A) CH3 – C – CH2 – CH2 – COCH2 – CH3
CH3 – CH – CH2 – CH
I: II : CH 3
OH O
O O
CH3 – CH – CH2 – CH (B) CH3 – C – CH2 – CH2 – C – CH3

III : H3C O
OH OH (C) O
(A) III (B) I, III (C) I, II (D) II, III H3C
CH3 CH3
Q.29 Order of rate of reaction of following com-
(D) CH3 – C – CH2 – CH2 – C – CH3
pound with phenyl magnesium bromide is:
O O OH OH
(I) Me – C – Cl (II) Me – C – H Q.34 Select the correct order of reactivity towards

O Grignard reagent for nucleophilic attack.
O O O
(III) Me – C – O – Et
(A) I > II > III (B) II > III > I (A) R – C – O – C – R < R – C – H
(C) III > I > II (D) II > I > III (B) Cl – CH2 – C – H > CH 3 – CH2 – C – H
Q.30 Select the correct order of decreasing reactiv- O O

ity of the following compounds towards the O
attack of Grignard reagent
(I) Methyl benzoate (II) Benzaldehyde (C) CH3 – C – O NO2 <
(III) Benzoylchloride (IV) Acetophenone
(A) II > III > I > IV (B) I > II > III > IV O
(C) III > II > IV > I (D) II > IV > I > III
CH3 – C – O
CH3MgX O O
Q.31 O Product is
NH4Cl
(D) R – C – OR > R – C – NH2
(A) Enantiomer (B) Diastereisomer
(C) Meso (D) Achiral Q.35 In the reaction sequence:
O
CH3MgBr
Q.32 CH3 – C – CH2 – CH2 – CH2 – Cl A, A
(i) CH3MgBr/CuCl
+
(X) Major + (Y)
O (ii) H2O/H
is
(X) & (Y) respectively
OH O O
CH3 OH +
H3O
(D) CH3MgX + C = O CH3 – C – OH
(A) ,
CH 3
Q.39 Which reaction gives 1º aromatic amine as
O major product.
CH3 OH
Br
(B) , (A) Mg/ether NH3
CH 3
O Br
CH 3 OH
CH 3 Mg/ether NH3
(B)
(C) , F
Br
OH CH 3
Mg/ether NH3
HO CH3 O
CH 3 (C)
(D) , F
Hg(OAc) 2
CH 3 OH (D) Ph
NH3/NaBH4
Q.36
(2) O
+
O OH H 3O
Q.40 CH3MgBr + CH2 = CH – C – H
C
Product (1,4 addition). It is
O (3)
H RMgX(2moles) OH
H
(A) CH 2 = CH – C – H (B) CH2 – CH = CH – CH3
S
C CH3 OH
CH (C) CH3CH2CH2CHO (D) None
(4)
Deprotonation will occur from the following
positions:
(A) 1,2 (B) 1,3 O
(C) any two positions (D) 1,4 O
Q.41 CH3MgBr(1eq.) ?
O
Br 14
(i) CO2
Q.37 Mg (A) + (B)
(ii) H /H2O OH
O O
NaHCO3
O
(C) gas (A) (B)
Product C is O
(A) CO (B) 14CO2
14
(C) CO2 (D) A mixture of CO2 and CO2 OH
O O
Q.38 Which of the following is incorrect O
(C) (D)
O
O
(A) C CH3MgX
Cl OC2H5 CH3–C–OC2H5
(1eq)
OC H O (i) Br2
2 5
C2H5MgX Q.42 CH2 = C = O (ii) CH3MgBr C4H8O
(B) CH3– C – OC2H5 (1eq)
CH3–C–OC2H5
(2 equi)
OC2H 5
O O
S S
+ CH 3
H 3O (A) (B) CH3 CH3
(C) CH3MgX + C = S CH3 – C – SH
CH3
(A) 7 (B) 6 (C) 8 (D) 5
O
(C) CH3 (D) All of these Q.48 Consider the given organometallic compound.
(I) (CH3)2Hg (II) (CH3)2Zn
RMgX (III) (CH3)2Mg (IV) CH3Li
Q.43 RMgX + CH3CN NH4Cl (A) (B)
NH4Cl The correct decreasing order of ionic character is
will be (A) I > II > III > IV (B) II > I > III > IV
(A) 1ºROH (B) 2ºROH (C) I > III > II > IV (D) IV > III > II > I
(C) 3ºROH (D) Alkene
(i) CH 3MgBr
O +
P
CH3MgCl
CH3 – CH2 – CH2 (ii) H 3O
Q.44 H2O Q.49 CH3CH = CH – C – CH3
O (i) CuI, CH3MgBr
+
Q
(A) CH3 – CH – CH2OH (B) CH3 – CH – CH2 – CH3 (ii) H 3O
CH3 OH OH
(C) CH3 – CH – CH3 (A) P is CH3CH = CH C Me ,
CH3 Me
(D) HO – CH2 – CH2 – CH2 – CH2 – OH O
Q.45 The reaction of 1 mole each of p-hydroxy Q is CH3 – CH – CH2 – C – CH3
acetophenone and methyl magnesium iodide
will give CH3
O
O
(A) CH4 + IMgO C – CH3
(B) P is CH3 – CH – CH2 – C – CH3 ,
O CH3
(B) CH3 – O C – CH3
OH
OMgI Q is CH3CH = CH C Me
(C) CH3 C OH Me
CH3 (C) P is CH3 – CH = CH – C(CH3)2 ,
MgI
O OH
(D) CH3O C – CH3 Q is (CH3)2 – CH – CH2 – C – CH3
O
(D) P is (CH3)2 – CH – CH2 – C – CH3 ,
Q.46 (i) + PhMgBr r1 PhCH2CH2OH
O O
(ii) + PhMgBr r2 PhCH2CH2CH2OH Q is CH3 – CH = CH – C(CH3)2
O
(A) r2 > r1 (B) r1> r2 OH
(C) r1 = r2 (D) r1 = 2r2
For Q. No. 50 to Q. No. 52
Consider the given reaction and answer the
Q.47 How many moles of Grignard reagent will be following questions
required by one mole of given compound? COOCH3
O
SH
HO C – OEt MeMgBr
O OCH3 (excess)
Products.
O SH
C – Cl O
CH2– CH2
O Q.50 No. of RMgX comsumed in the reaction is
Cl (A) 4 (B) 5 (C) 6 (D) 7
Q.51 How many product will be fromed in given

reaction (excluding stereo)
(A) 2 (B) 3 (C) 4 (D) 5
Q.52 Which of the following reaction will gve the

same Hydrocarbon formed as one of the prod-
uct in the above reaction.
(A) EtMgBr + Me–OH 
(B) PhMgBr + Me–OH 
(C) MeMgBr + Ph–OH 
(D) MeMgBr + CH3–CHO 

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GRIGNARD REAGENT Page # 15

Exercise - I (Only one option is correct)

Q.1 C6H5COOH + CH3MgI  ?

Q.3 The reactivity order of CH3MgBr with the following

(A) HO – CH2 – C – CH3 (B) Cl – CH2 – C – OEt O O

Q.9 Match List –I & List – II and select the correct

Code i ii iii iv Q.15 One conversion into Grignard followed by

MgBr OH C6H13 C6H13

(C) HOCH2COOC2H5 3 (D) 4 O

CH3 – CH – CH2 – CH (B) CH3 – C – CH2 – CH2 – C – CH3

(I) Me – C – Cl (II) Me – C – H Q.34 Select the correct order of reactivity towards

Q.30 Select the correct order of decreasing reactiv- O O

Q.51 How many product will be fromed in given

Q.52 Which of the following reaction will gve the

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