ORGANIC CHEMISTRY

Master Practice Problems

Target IIT JEE-2020
RAPID CRASH COURSE

MPP-2

Single correct :

Q.1 KSH


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

Q.2 True statements regarding SN1 reaction is/are

(A) Perfect racemisation is observed
(B) Only Walden inversion is observed
(C) Total retention of configuartion is observed
(D) None of these
Q.3 Which is most reactive towards nucleophilic aromatic substitution.

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

Comprehension :
Paragraph for Question Nos. 4 to 6
Preparation of Grignard reagent.
 
R–X + Mg Et
  R  Mg  X (Organomagnesium halide)
2O

Grignard reagent may be made from primary, secondary and tertiary alkyl halide as well as from vinyl
halide and aryl halides. Grignard reagent is strong nucleophile and strong bases.

O
||
Q.4 PhMgBr + CH 3  C  Et (  (P)
ii ) H 

Major product (P).

OH Et OH
| | |
(A) Ph  C  Et (B) Ph  C  CH 3 (C) Ph  C  Ph (D) None
| | |
CH 3 CH 3 Ph

1
Q.5 In which of following reaction tertiary alcohol will be obtained as a product.
O
(A) C—CH3 + Et MgBr ( 
ii ) H 

O
||
(B) Ph  C  Cl + excess PhMgBr ( 
ii ) H 

O
||
(C) Cl  C  O  Et + excess PhMgBr ( 
ii ) H 

(D) All

Q.6 Ph  CH  OEt CH

3MgBr
 (P) + PhMgBr (  (Q)
ii ) H 
|
OH

End product (Q) is

O O
|| ||
(A) Ph  CH  CH 3 (B) Ph  C  Ph (C) Ph  C  H (D) Ph  CH  Ph
| |
OH OH

More than one correct :

Q.7 CD 3  CH  CH 3 alc
.KOH


|
Cl

True about above reaction is/are:

(A) It is E2 elimination
(B) Saytzeff's alkene is major product in above reaction
(C) CD3–CH=CH2 is major product
(D) It is anti elimination

Q.8 Which of the following can give ppt. of AgCl with both aq. AgNO3 & alc. AgNO3.

(A) (B)
Cl Cl

(C) (Me3C)3C–Cl (D) Cl

Q.9 Methane will be produced in which of the following reaction:

LAH
(A) Be2C H
2O
  (B) CH3OH 
Na
(C) CH3–Cl EtOH
 (D) Al4C3 H
2O
 

2
Q.10 Select correct statement about the products.

red P
H P1
OH Br2

HBr
P2
S-3,3-Dimethyl
SOBr2
Butan-2-ol P3

(A) P1 & P3 are identical (B) P1 & P2 are positional isomers

(C) P1 & P3 are enantiomers (D) P2 & P3 are positional isomers.

Q.11 Which reaction is / are correct. (Only organic products are given)
(A) H3C–O–CH2–CH3 + PCl5  H3C –Cl + Et – Cl

(B) H 3C  C  OH + PCl5  H 3C  C  Cl
|| ||
O O

(C) H 3C  C  CH 3 + PCl5  H 3C  CH  CH 3
|| |
O Cl

OH Cl

(D) + PCl5 

Q.12 In which of the following reaction correct product is given

Me Me
MeONa
(A) Ph – Cl aq
.KOH
 PhOH
 (B) H I  
 MeO H
D D


(C) C  C  C  C  

C–C–C=C (D) conc
 .H 2SO 4

| OH 
 NMe3 OH

3
Match the column :
Q.13 Column I Column II
(Reaction) (Major product)


(A) OCH 3
  (P)
Cl OCH3

( i ) Hg ( OCOCH ) .CH OH
3 2 3
(B)        (Q)
( ii ) NaBH 4 / OH ¯

Br
(C) AgCN
 (R) CN
+
(S) NC¯

Subjective :

Q.14 Number of compounds which are more reactive than H 3C  CH — Cl by SN2 mechanism ?
|
CH 3

O
Cl
F Br
Br I
Cl

Cl

H3C – Cl

Cl

Q.15 Number of compounds which can show Haloform reaction.

D D H 14 14
CD3 H3C 14 CH3

O H O O
O

Cl H
H

H OH OH
O

O D3C  C  C  OH
|| | |
O O

4
Q.16 Number of structures of trichloroderivatives of cyclohexane are ?

Q.17 How many moles of Grignard's reagent will be consumed per mole.

Cl
O
C OMe
Cl
H Cl

Q.18 Consider following reactions:


HBr / H 2O 2
(a)    KCN
 H/
H 2O


O

(b) Cl NH

PCl H / H 2O
3  5    


(c) HBr
 AgCN
 H/
H 2O


(d) H  / CO / H O
2
    
( i ) BH .THF
(e)  3  Jone
 's reagent
 
(ii ) H 2O 2 / OH ¯

Number of reactions which can produce Butyric acid as major product is / are_____.

Q.19 Consider following compounds.

Br
Cl
Ph3C – Cl
Cl Cl
Cl

Br Cl

Number of compounds in above compound which are more reactive than Cl for S 1 reaction is
N

/ are _____.

5
 ANSWER AND SOLUTION
Single correct :
Q.1 (D)

Q.2 (D)

Q.3 (B)

Sol. Due to –I high electronegativity of F it stabilizes Cr formed in rds ]

Q.4 (A)
O OMgBr OH
+
H
Sol. Ph-MgBr + CH—C—Et
3 CH—C—Et
3 CH—C—Et
3 ]
Ph Ph
Q.5 (D)

O OMgBr + OH
H
Sol. (A) C—CH3 + EtMgBr C—CH3 C—CH3
Et Et
3° alcohol

O O O
|| | ||
(B) Ph – C – Cl + PhMgBr  Ph – C – Cl  Ph – C – Ph PhMgBr
|
Ph

OH OMgBr
| |
H
Ph – C – Ph  Ph – C – Ph
| |
Ph Ph
3° alcohol

O O O 
|| | || PhMgBr
(C) Cl – C – OEt + PhMgBr  Cl – C – OEt  Ph – C – OEt
|
Ph


OH OMgBr O O
| | || |
H ]
Ph – C – Ph  Ph – C – Ph Ph – C – Ph 
 Ph – C – OEt

| | PhMgBr |
Ph Ph Ph

6
Q.6 (D)

O 
OH
CH MgBr
|| PhMgBr |
3 Ph – C – OEt
Sol. Ph  CH  OEt Ph – C – H + Ph – CH – Ph ]
| Br (ii) H
OH OMgBr Mg
 OEt

More than one correct :

Q.7 (A, C, D)
Sol. B.E. C–D > C–H
H effect H > D
Stability CD3–CH = CH2 < CH3–CH = CD2

Q.8 (A, B, C)
Sol. A,B,C all capable of giving SN1

Q.9 (A, C, D)
Sol. (A), (C), (D)
Be2C + 4H2O  CH4 + 2Be (OH)2
Na
CH3–Cl CH4
EtOH
Al4C3 + 12 H2O  3CH4 + 4Al(OH)3

Q.10 (B, C, D)
Br H
Br Br
H
Sol. P1 ; P2 ; P3

Q.11 (A, B, D)
Cl
|
Sol. H 3C  C  CH 3 + PCl5  CH 3  C  CH 3
|| |
O Cl
Q.12 (B, C, D)
Sol. (A) Ph – Cl aq
.KOH
 PhOH

Me Me
– 
MeO Na
(B) H I SN2 
 MeO H
D D

(C)  

OH

NMe3

7
 
(D) conc
 .H 2SO 4
 

OH

Match the column :

Q.13 (A) Q (B) P (C) S

Sol. (A) 
OCH3
 
Cl

( i ) Hg ( OCOCH ) .CH OH
3 2 3
(B)       
( ii ) NaBH 4 / OH ¯
OCH3
Br
(C) AgCN
 CN

Subjective :
Q.14 [5]

Q.15 [6]

Q.16 [6]

Cl Cl Cl Cl Cl Cl Cl Cl Cl
Cl Cl Cl
Sol.
Cl Cl Cl Cl
Cl Cl

Q.17 [4]

Q.18 [3]

Q.19 [4]