Ex 1

Solutions Slot – 1 (Chemistry) Page # 1
G.R.
EXERCISE – I SINGLE CORRECT (OBJECTIVE QUESTIONS)

Sol.1 C CH3
C6H5–COOH + CH3MgI  CH4+C6H5COOMgI Cl–CH2–C–OEt + CH3MgI Cl–CH2–C–OEt
O OMgI
Sol.2 D OEt
MgI
Br MgBr
Cl–CH2–C–CH3
ether
+ Mg O
CH3 CH3
H2O
Cl–CH2–C–CH3 Cl–CH2–C–CH3
F F CH3MgI
OH OMgI
[reactivity order of alkyl halide for G.R.]
Sol. 6 A
C – I > C – Br > C – Cl > C – F
Mg
2CH2=CH–CH2–Cl CH2=CH–CH2MgCl
ether
Sol.3 A H–C–OEt
O
OH
CH2=CH–CH2–CH–OEt
CH3 CH3 CH3 – C – Cl
C OMgX
CH3–Cl
O O OEt
(III) Mg
(II) (IV) X
(I) CH2=CH–CH2MgCl
(CH2=CH–CH2)2–CH CH2=CH–CH2–C–H
reactivity order of CH3MgBr with following com- OMgX O
pound. H3O
I > IV > II > III (CH2=CH–CH2)2–CH–OH
Sol.4 C Sol.7 D
(i) Et2O
CH3 – CH – CH2 + (CH3)2CHMgBr
(ii) H 2O  
O CH–CH–MgI
3 2
CH2–CH2–I
CH3 – CH – CH 2 – CH(CH3)2 CH–C–Cl

2
CH2–C–Cl Mg / ether
 
OMgBr O
H 2O O
F
F
CH3 – CH – CH 2 – CH–(CH3)2
OH
Sol.5 D
CH3 O
Followed
Cl–CH2–C–OEt + 2CH3MgI by H2O
Cl–CH2–C–CH3
O OH
394 - Rajeev Gandhi Nagar Kota, Ph. No. 0744-2209671, 93141-87482, 93527-21564
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Page # 2 Solutions Slot – 1 (Chemistry)
Sol.8 B R R
(D)  
 H3O  
1 CH3Mgx RMgx + Ph–C N Ph–C=NMgx Ph–C=O + NH 2Mgx
HO–CH2–CH2– C –CH2–CH2– C –oet
|| || –CH4
O O
Sol.10 D
XMgO –CH2–CH3– C –CH2–CH2– C –OEt R

|| ||  
O O (a) RMgx + CH 3 – C N CH3–C=NMgx

(P) H3 O
R
X
CH3Mgx CH 3–C=O+Mg
NH2
CH3
(b) RMgx + C = S R–C=S
|
  
XMgO –CH2–CH2– C  CH2  CH2  C –OEt (Q) S S Mgx H3O
|| R–C=S
|  O

OMgx SH
(Dithionic Acid)
CH3Mgx R
(c) RMgx + Cl–C–OEt
Cl–C–OEt
 
CH3 CH3 S OMgx
| |
XMgO –CH2–CH2–CH2– C  CH2  CH2  C  OEt R–C–OEt
|  |
  O
OMgx OMgx
 
(R) (D) RMgx + CH 2– CH 2 R–CH–CH–OMgx
2 2

O HO
3
Sol.9 B R–CH–CH–OH
2 2
  Sol.11 A
(a) H3O
RMgx + HCHO  R–CH2– O M gx   R–
–
CH2–OH O OMgx

1 mole CH3 Mgx CH3

  H3O
(b) RMgx + (CH2)2O R–CH2–CH2–OMgx RCH2–CH 2–OH +H O
O O
H2 O
CH 2–CH2 O O
O
OH

  H3 O CH 3
(c) RMgx + C=O R–C–OMgx R–C–OH
O
O O O O
Sol.12 C
Mg ether
Br–CH2–CH2–CH2– (4) CH2  CH  CH2  CH3     CH3–
| | C2H5OH
X CH3
Et2O  
Br+Mg   BrMgCH2–CH2–CH2–Br CH  CH2  CH3
|
CH3
+ MgBr2
Sol.16 C
CH3MgBr + C 4H9NH2  CH4 +
Sol.13 A (excess)
Reactivity of Alkyl halide for
 
R–X+mg  RMgx C4H9 NHM gBr
 (R–I > R –Br >R–Cl)
.595 gram
Sol. 14 D  .05 .05 mole .05 mole
119
Mg
Br–CH2–CC–CH2–Br  BrMgCH2–CC–CH2MgBr
(excess) CH4 (in liter)  .05 × 22.4  .112 liter
Et2O
Mg(1eq) Sol.17 C
et2O  
CH2 = C H M gBr + CH  CH  CH2  CH2
2 mole 1 mole 2 mole
 
BrMgCH2–C C–CH2–Br
2.62 224 ml
= .02 = .01 .02
131 22400
CH2=C=C=CH2
CH2=CH2 (in liter)  .02 × 22.4  0.448 liter
Sol.15 C
Sol.18 A
Mg ether
(1) CH3– CH  CH2 –CH2–x     CH3–
| C2H5OH
MgBr OH
CH3 
OMgBr
CH  CH2  CH3 + +
|
CH3
Mg ether
(2) CH3– CH  CH  CH3     CH3– Sol.19 D
| | C2H5OH
CH3 x Cl 1 equivalent mg
      
ether
CH  CH2  CH3
| Br
CH3
X
| Mg ether
(3) CH 3 – C  CH2  CH3     CH 3 –
C2H5OH Cl
|
CH3 D O
2
 + MgBrCl
 MgBr
CH  CH2  CH3
|
CH3
Sol.20 A

R OMgx

(A) CH3– C–OC2H5+RMgx  CH–C–OC
3 2H 5 OH
OH
O OMgx

(D) (4) RMgx CH–R
2 RMgx    

CHO R–CH–OH
CH3–C–R
COOC2H 5 R
R
R O
H2O CH3–C–R
CH3–C–R   Sol.21 (I > II > III > IV) (A)
–Mg(x)(OH) OMgx RMgx Reactivity order of following carbonyl comp.
OH
with G.R.
H
H C=O
R C=O
 (i) (ii) CH 3
(B) CH–C–Cl
3 + RMgx CH–C–Cl H
3 +I

OMgx
O
2RMgx CH–C–R
3 +I +I
CH3 Me3C
O
(iii) C=O (iv) C=O
RMgx CH3 Me3C
R +I +I
CH–C–R
3
More ve charge at carbon in – C – bond will
||
R  OMgx O
H3O
CH–C–R
3
be more reactive for G.R.
OH
Sol.22 C
CH3MgBr  CH3
(C) HO–CH2– C –OC2H5    BrMgO –
|| (i) Mg
O C 6H 13 * Br
(ii) CO2
CH2– C –OC2H5+CH4
|| H (iii) H
O (R)–2–Bromooctane
3 RMgBr
CH3 CH3
(R)
C 6H 13 * COOH + HOOC * CH 13
2CH3MgBr
(S)
H H
CH3
  |
BrMgO CH2 – C  CH3
|
OH
Sol.23 C Sol.26 B
  H  2 Br
(A) RMgx + CO2  R– C – O M gx   CH3–CH=CH2  
 CH2  CH  CH2
 |
||
O Br
R– C –OH 
|| CH–CH=CH
2 2
O 
MgBr O
X CH–C–CH
3 3
(B) RMgx + C2H5OH  R–H + Mg
OCH
2 5
(C) RMgx + CH3–CH2–Cl  R–CH2–CH3 +

X CH3 CH3
Mg H / 
CH–C–CH–CH=CH
3 2 2
 
 CH–C–CH–CH=CH
3 2 2
Cl 
OH O Mgx
(D) RMgx +

Cl O R O +MgxCl CH3
CH–C=CH–CH=CH
3 2
Sol.24 A
O OEt
R OH
HO C–Oet no. of RMgx   Sol.27 MgBr + H–C OEt
Mgx O C
1 R
OEt
O 1
R 2
OH
Sol.28 C
 no. of G.R. (RMgx) consumed per mole
compound = (4)
Br MqBr
1 Mg/ether
+CH–CH–CH–C–H
3 2
Sol.25 D OH O
(A) C  C  C  C + Mg 
| | OMgBr H
Br Br (CH–CH–CH–CHO)
3 2 +

HO
3
BrMgC–C–C–CMgBr
[CH–CH–CH–CHO]
3 2
OH
Cl
(B) +Mg  +MgCl 2 Sol.29 A

Cl Reactivity order of following with PhMgBr
CH3 Me
Mg / Zn dust (I) C=O (ii) C=O
(C) C  C  C      C–C=C(Alkene)
Cl H
| |
Cl Cl –I
(D)
Me
 (iii) C=O
Zn/Mg
CCC  C – C – C + MgCl2 eto
| | 
Cl Cl MgCl +M
Cl
I  II  III
Sol.30 C
Decreasing reactivity order of following comp. toward CH3 OC2H5
attack of G.R.
CH3 
O OMgx
Ph Ph
(i) C=O (ii) C=O
CH3O H
+m 
Benzaldehyde HO
3
Methyl benzoate x
–Mg
OC 2H 5
Ph Ph
(iii) C=O (iv) C=O
Cl CH 3
–I +I
Benzoyl chloride CH 3 O
Acetopheno
CH3 O
III  II  IV  I
Sol.34 B
Sol.31 A (Reactivity order towards G.R. for Nu attack)
O O O
 CH3 CH3
CH3Mgx
O + (A) R–C–O–C–R > R–C–H
NH4Cl
OH OH
due to good leaving group
Sol.32 C
Cl–CH–C–H
2 > CH–CH–C–H
3 2
(B) –I
 CH3 O O
CH 3MgBr
CH3–C–CH2–CH2–CH2–Cl CH3–C–CH2–CH2–CH2–Cl O O
 –M, –I
O  
OMqx (C) CH3–C–O NO2 > CH3–C–O
CH3 O O
CH3 ||
O (D) R– C – NH2 > R–C–OR
Sol.33 C Acidic H
Sol.35 B

(i) CH3MgBr O OMgBr OH
CH–C–CH–CH–C–OCH–CH
3 2 2 2 3
(ii) H O3
(i) CH3 MgBr/CuCl H2O
O O (ii) HO/H 
2
CH3 CH3
CH3
Tautomerism
CH3–C–CH2–CH2–C–OC2H5

OMgx O
 O
CH 3
Sol.36 A
 
O OH (D) CH3Mgx + C=O CH 3–C–OMgx
C
O O
O
H3O
H
H
S CH3–C–OH
C
O
CH

O OMgx
Sol.39 B
C
+
O Br MgBr H
RMgx (2 mole) H (A) Mg/ether NH3
   

 
XMgS
+
C Br MgBr
Mg/ether
CH (B)
F
More Acidic H react with R Mgx and gives
Alkane. NH2
NH3
Sol.37 A
14
Br  C OH
14 +
Mg MgBr (1) CO2 Br
O MgBr
Mg/ether
(C)
NaHCO3
14
C ONa F
+ CO2
F
O
H
Sol.38 B NH3

O  OMgx
CH 3Mgx
(A) CH–C–OC
3 2H5
+Mgxcl
(1 eq)
Cl OC 2H 5 Cl CH OC2H5 F
3 O NH2
Hg(OAc)2
(D)
OC2H 5  Ph Ph CH3
NH3/NaBH4
C 2H 5Mgx
(B) CH3–C OC2H 5 CH 3–C–C2H 5
(1 eq)
OC2H 5 sol. 40 C
OC2H 5 OC2H 5 O
   CH3 mgBr+CH2=CH—C—H
(C) CH3Mgx + C=S CH3–C–SMgx
+
S S Omgx
H H3O
+
CH 3—CH 2—CH=C—H
+
CH3–C–SH H3O
S
O Br
Tauto merism (i) Br2 CH2—C=O

CH3—CH2—CH2—C—H CH2=C=O
CH3 MgBr
Br
OH Br
CH3—CH2—CH=CH CH2—C—O MgBr
Br CH 3
Sol. 41 D
O O
CH3 CH 3
CH 3 MgBr
CH2–C=O CH 2–C–OMgBr
O
Br Br CH3
CH 3
+
OMgBr CH2–C–CH3
O
CH3
Br
OMgBr
CH3 mgBr (1 eq)
O
CH3
CH3
O
O CH2—CH3 +MgBr2
O
sol.43 C
O R
+
R Mgx + CH3CN CH3—C=N Mgx

NH4Cl
Sol. 42 A
R
CH3—C=O
R Mgx
R
+
R CH3—C—O Mgx
NH4Cl
CH3—C—OH R
Sol.44 B
CH 3MgCl
CH3—CH—CH2 CH3—CH—CH2—CH3
O +
O Mgx
+
H3O
CH3—CH—CH2—CH3
OH
Sol. 45 A
O O
HO C—CH3 + CH3 Mg I CH4 + IMg O C—CH3
Sol 46 B
r1 r2
+ Ph Mg Br + Ph Mg Br Ph
Ph O
O
+
O Mgx O MgBr
r1>r2
H2O H2 O
Ph Ph OH
OH
3 Membred ring having more angle strain than 4 membred ring
Sol. 47
1 mole of R Mgx
1 mole of R Mgx
SH
O
2 mole of RMgx
NH2
C—oet
C—Cl
O
CH 2—CH 2
2 mole of RMgx
Cl
1 mole of RMgx
Total No. of R Mgx consumed in above comp = 7
Sol.48 D
decreasing order of ionic character in following organo metallic compond
CH3–Li > (CH3)2 Mg > (CH3)2 Zn > (CH3)2Hg
[ ionic character  difference between E.N.]
Sol. 49 C
O O mgx
(i) CH 3 mgBr
CH3—CH=CH—C—CH3 CH3—CH=CH—C—CH3
CH 3
(i) Cu I, CH3 MgBr
(ii) H 3O H 3O
OMgBr
CH3—CH—CH=C—CH3 OH
CH 3 CH3—CH=CH—C—CH3
H 3O CH3
OH
CH3—CH—CH=C—CH3
CH 3
O
Tautomerism
CH3—CH—CH2—C—CH3
CH3
Sol.50 C
2 mole of
O R Mgx
C—OCH3
MgBr
(excess)
O OCH3
O
O SH
1 mole of
3 mole of R Mgx
R Mgx
Total No. of R mgx consumed in one mole above comp = 6
Sol.51 C
(i) SH+CH3MgBr S Mg Br + CH4
O O MgBr
(ii) C—OCH3+CH 3 MgBr C OCH3
CH 3
O
C—CH3
(iii)
OMgBr
O O
CH3MgBr OMgBr
O
O CH 3 O–C–CH 3
O
Br O
3
Mg
CH
OMgBr OMgBr
CH3–C–CH3 + CH3
O OMgBr O–C–CH3
OMgBr
Sol. 52 Me MgBr+ PhOH  Me—H+ Ph O MgBr

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Solutions Slot – 1 (Chemistry) Page # 1

EXERCISE – I SINGLE CORRECT (OBJECTIVE QUESTIONS)

CH3 – CH – CH 2 – CH(CH3)2 CH–C–Cl

XMgO –CH2–CH3– C –CH2–CH2– C –OEt R

(C) RMgx + CH3–CH2–Cl  R–CH2–CH3 +

(B) +Mg  +MgCl 2 Sol.29 A

Tauto merism (i) Br2 CH2—C=O

CH3—CH2—CH=CH CH2—C—O MgBr

R Mgx + CH3CN CH3—C=N Mgx

HO C—CH3 + CH3 Mg I CH4 + IMg O C—CH3

3 Membred ring having more angle strain than 4 membred ring

Total No. of R Mgx consumed in above comp = 7

Total No. of R mgx consumed in one mole above comp = 6

(i) SH+CH3MgBr S Mg Br + CH4

(ii) C—OCH3+CH 3 MgBr C OCH3

Sol. 52 Me MgBr+ PhOH  Me—H+ Ph O MgBr

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