Answer Key

DPP - 1

1. A 2. B 3. B 4. D 5. D 6. D 7. D
8. A 9. A 10. A 11. B 12. C 13. C 14. C
15. B 16. BC 17. 3 18. 9

DPP - 2

1. D 2. C 3. C 4. D 5. D 6. D 7. D
8. D 9. D 10. C 11. B 12. D 13. C 14. B
15. 5 16. 8 17. 2 18. 2

DPP - 3

1. C 2. C 3. B 4. A 5. B 6. C 7. B
8. C 9. B 10. B 11. C 12. C 13. D 14. CD
15. B 16. C 17. C 18. 8 19. 3 20.

DPP - 4

1. D 2. A 3. B 4. C 5. D 6. A 7. B
8. C 9. C 10. C 11. D 12. B 13. D 14. BC
15. ABD 16. AB 17. 4 18. A-Q,R ; B - P ; C - P; D - P, S

DPP - 5

1. A 2. A 3. B 4. C 5. D 6. B 7. C
8. A 9. C 10. D 11. B 12. B 13. B 14. B
15. B 16. A 17. C 18. B 19. A 20. D 21. B
22. A 23. ABC

DPP - 6

1. B 2. B 3. D 4. B 5. B 6. C 7. D
8. D 9. C 10. A 11. BC 12. ABCD 13. AC 14.
15. 9

DPP - 7

1. C 2. D 3. B 4. C 5. B 6. D 7. B
8. C 9. B 10. A 11. A 12. C 13. BC 14. BC
15. (A-P,R,S,T) (B-Q,T) (D-Q,T) 16. 3

DPP - 8

1. C 2. A 3. D 4. B 5. A 6. D 7. A
8. C 9. B 10. C 11. CD 12. B 13. D 14. 3

DPP - 9

1. D 2. D 3. C 4. C 5. C 6. C 7. C
8. A 9. D 10. D 11. D 12. AB 13. B 14. 5
15. 4
1. A
Br

Na
D.E.

Mech 2 Na 2 Na
+ 2e

2 Br 2

2. B Br
Na
D.E.

Br

Br Br Br
2Na 2Na+2e R.S.
+ 2NaBr

Br

3. B
Br
Na / D.E Se

Br
(A) (B)

4. D

CH3 CH3 CH3 CH 3

Na /D.E
Na Na + e
–NaCl
Cl Cl Cl

CH3 CH3
5. D

Na / D.E R.S
Cl
Na - Na + e

6. D
CH3 Coo K Eletrolysis CH 3 - C 2 H5
+ +
Et - Coo K C2 H5 - C2 H5 + 2Co2 + KoH + H2
+ Cathode
CH3 - CH3

Anode

Anode O

Cathode
O
H +H
H +e H2
K + H2O KOH

7. D
O O

C - O Na C-O
electrolysis
+ 2Na
C
C - O Na C-O

O O

Anode Cathod

-e Na

O
H—OH +NaOH
C-O

H
C-O
O
H
O HO H2
Co 2

(2-butyne)
8. A
in Kolbe’s eledrolysis process. NaOH / KOH is Formed at cathod so PH increases and POH
decrease
At cathod = Na + H2o NaoH + ½H2 g))

9. A
NaOH CaO
CH3 COOH CH3 Coo Na CH3 + CO2

NaOH CaO
CH3 - CH2 -COOH CH 3 - CH 2 - Coo Na CH 3 + CH2 + CO2

NaOH CaO
CH3 - CH -COOH CH3 - CH - Coo Na CH3 + CH +CO2

CH3 CH3 CH3

[ rater of decorboxylation  stability of corbanion ]

rate of decorboxylation = r1 > r2 > r3

10. A
O

C - O Na

o o o

11. B

Br

NBS Wurtz
  
reaction


12. C
Dry  ether
R + Cl + 2Na + Cl - R   R R + 2NaCl
(Symmetric Hydrocarbon)

(C) Dr  ether
Cl + 2Na + Cl 

(2,3-dimethyl butane)

13. C
2Na
 Na C  C Na  H2 gas
HC  CH 
14. C
O

C 2 H5 C OH + KOH C 2 H5 COO K

O

CH5C 2 O C 2H 5 C O (Anode)

O

C 2 H5 C O C2H5 + CO 2


2CH3 – C H2 
 CH3  CH2  CH2  CH3


CH3 CH2 + H CH2 CH3 CH3 CH3 + CH 2 = CH 2

15. B
Na
R  Cl 
Dryether
R  R Symm alkane only 
It is a coupling reaction in which only one type of R–Cl is used otherwise multiple products
are obtained.

Multiple Choice Questions

16. BC
- + Kolbe's
COO K  CH2
electrolysis
CH2 CH2
- +  CH2 (Acetylene)
COO K

(salt of succinic acid) 2CO2

- +
COO K
Kolbe's
 CH2
electrolysis
CH2 CH2
+-
K OOC  CH2 (Acetylene)
(salt of fumaric acid)
2CO2

Integer Type Questions

17. 3
Br

Na 


D.E.
 
14 14
14
2 Different radicals will give 3 different products.
 14 14

14
14 14

14

18. 9

I
Cu/ 
Number of resonanting structure are 9.
I
1. D
D2/Pt
+ D D
(syn addition)

D D H H

2. C

3. C

4. D

CH3 CH3

D D
D2/Pt
+
D D
CH3 CH3

Identical

5. D

CH3 CH3

H H
H2/Pt
+
H H
CH3 CH3

Identical
6. D

R R
R—C==C—R

NH3

R—C==C—R
H
NH3

H R
C==C
R H
Trans Alkene
H2 + Pd (CaCO3 + Qunoline)
Cis Alkene
P—2—catalyst
Raney Ni

7. D

Na/liq. NH3 CH3 H

C==C
Li/leq. NH3 H CH3
Li/et OH (Trans-2-butene)

8. D

Na/liq. NH3 CH3 H

C==C
H CH3

Na/liq. NH3
CH3—CH ==CH2

9. D

more collision probablity having triple bond than

double bond. Reactivity order of catalytic hydrogenation C>a>b

10. C

D D
D2/Ni
+
(syn)
HO H (trans) HO H HO H
D D

Pair of diastereomers

11. B

CH3 Me Me
2 H

Ni, 
 +
H H H
H H Me
CH2 Me
(3) (a) (b)

a, b  stereoisomers
a  achiral (meso)
b  ohiral

12. D

* *

(1) (1) (2) (2)

13. C
Li/NH3 (birch reduction) gives trans alkene.

14. B

H
2
Ni/ 
 (i)

(ii)

(iii)

15. 5
16. 8

X=6 n = 3 ; 23–1 + 22–1  22 + 21 = 6

Br Br Br
Br Cl
Cl
Y=4

Cl

Cl

O
CH2

OD /D O
Z=6  2

 CD3
Polonged treatment  D D
D
17. 2+0=2
(i) After hydrogenation we get here we get 3 aromatic +4 non aromatic rings in all other
cases we get at least 1 anti aromatic ring which is very unstabl. Prossible isomers.

All three on the same side Any two on same side

Hence x = 2.
(ii) For a meso product, we need at least 2 chiral centres.
After dibromination we don't get any such products.
Hence y = 0
x+y=2

18. 2

Ni/H 2
1. C
Cl2
CH3 - CH2 - CH2 - CH2 - CH3 CH3 - CH2 - CH2 - CH2 - CH2 - Cl
hv
+
R/S
CH3 - CH2 - CH2-CH - CH 3

Cl
+
CH3 – CH2-CH - CH2 - CH3

Cl

2. C
Cl2 / hv
CH3 - CH - CH-2 CH2–CH3 CH3 - CH - CH2 - CH2 - CH2 - Cl
F.R.S
CH3 CH3

+
R/S
CH 3 - CH - CH2 - CH - CH 3

CH3 Cl
+
R/S
CH 3 - CH - CH - CH 2 - CH 3

CH3 Cl
+
Cl

CH 3 - C - CH2 - CH2 - CH 3

CH3
+

H
R/S
Cl - CH2 - C - CH2 - CH2 - CH3

CH3
Total no of monochloro product = 8
3. B

CH 3 H CH3 CH3 H CH3

Br2 / hv

H H H H Br H

hv
Br2 2 Br

CH3 H CH3
H
Br2 / hv
CH3 - C - CH3 CH3 - C - CH3
Br
CH 3 CH3
- HBr
H H H
(Neuman Formula) Br2

Br

CH3 - C - CH3

CH3

4. A

H H H CH3 H
H
H H H

CH 3 H CH3 CH3 CH3 CH3

H H H
(I) (III)
(II) CH3

CH 3 - CH - CH 3 CH3 - C - CH2 - CH 3

CH3 CH3 - CH3 CH3

Br2 / hv Br2 / hv
Br Br2 / hv
CH3
CH3 - C - CH 3 CH3 - C - CH - CH3
CH3 - CH2- Br
CH3 CH3 Br

[ Most stable free radical is formed as intermidiate ]

Order of Bromination = I> III > II >
5. B
Cl Cl Cl

Cl
Cl Cl
(1) (3) (2)
2-pairs of diastereomers M=5

6. C

(A) 2 Cl /Light

 Cl + +

Cl
(active)

Cl Cl
Cl /Light
*
(B) 2

 + + +
Cl
* Cl
(active)
Cl
Cl
(C) Cl2 /Light +



*
(D) Cl /Light
2
Cl +


Cl
(active)

7. B

Cl
Cl + (Both achiral)

8. C Cl
Cl2 *
CH3 CH CH2 CH3 (i) CH3 CH CH2 CH3 (R + S)
hv
CH3 CH3

Cl
(ii) CH3 C CH2 CH3
CH3

Cl
*
(iii) CH3 CH CH CH3 (R + S)
CH3

Cl
(iv) CH3 CH CH2 CH2
CH3
9. B

Cl
Cl2/light Cl +

(Iso-butane)

10. B

11. C

, ,

12. C

13. D

14. CD
Bond dissociation energy of I2 is maximum.
F2 has lower bond dissociation energy than Cl2 or Br2.

15. B
16. C

 Total after fractional distillation = 3

17. C

18. 8
Cl

2Cl /HCl Cl
2
Dichlorination
 +

19. 3

20. Compound Structural isomer Total isomer

I 1 1
II 2 2
III 2 3
IV 2 2
V 3 4
VI 4 6
VII 1 1
VIII 4 8
IX 5 12
X 1 12
XI 2 3
1. D

2. A

Enantiomers are not separated by fractional distillation as they have same B.P.

3. B

4. C

5. D

(A) (B)

(C)  (2) (D)  (3)

6. A
F2 > Cl2 > Br2 > I2

7. B
 
CH3 – CH3  CH3 CH2  H

8. C
Free radical is intermediate in halogenation reaction so 3°radical is most stable.

9. C
B.P.  Surface area
M.P.  Close packing

10. C

11. D

12. B
Formation of alkyl free radical is rate determining step.

13. D
Bromine atom has a much higher regioselectivity than chlorine atom in abstracting 3°
hydrogen.

14. BC

* Cl
* Total 4 stereoisomers

H Me H Cl H Me Cl H Me H Cl H Me H H Cl

(1) (2) (3) (4)

Diastereomer Pairs : (1,2), (2,3), (3,4), (1,4)

Cl
*

Cl Cl Cl
Enantiomeric Pairs (No diastereomeric Pairs)
15. ABD

(A)  POS + 2 chiral centre

(B)  POS + 2 chiral centre

(C) no meso possible

(D)  POS + 2 chiral centre

16. AB

(A)  Chiral centre, No POS, COS, optically active

e

(B)

17. 4

18. A-Q,R ; B - P ; C - P; D - P, S

Sol. (A) 1

(B) 2

(C) 2

(D) 6
1. A
Cl
H
HCl Cl
Peroxide

2. A

3. B
Anti-Markownikoff’s addition of HBr is operate at unsymmetrical Alkene so but-2-ene are
symmetrical Alkene not operate Anti Markownikoff’s addition of HBr.

4. C

5. D
Br
HBr Ring expansion Br
6. B

7. C

8. A +
H Cl
– +
Me—CH—CH=CH—Ph Me—CH—CH2—CH—Ph
Et Et

–
Cl

Cl
Me—CH—CH2—CH—Ph

Et
9. C
CH3 CH3

CH2 CH3
HBr
CCl4

Br Br

CH3 CH3

CH3 CH3

Br Br

Diastereomers
10. D

11. B

HBr/40°C
(T.C.P.)

Br

Br

12. B

HBr
CH3CH=CH CH3 OH   CH3CH2 CH OH
Br
13. B

Br

HBr/CCl4

Positional isomers

Br
HBr/R2O2
Hv

14. B

Br

CH 2 HBr/CCl4 (major) According to markovnikov addition rule

(A)
CH2 - Br

HBr/R2O 2
Hv (major) According to anti-markovinkov addition rule

(B)
A and B are positional isomers.

15. B
Br

H Br

in CCl
 + Ionic-addition
4
Racemic
(Symmetic alkene)
mixture (±)

Br

H Br
  + Radical-addition
in
R–O–OR Racemic
peroxide effect 
mixture (±)

16. A
Br
HBr 2 4 ; Addition according to Markovnikov rule
1 3
CCl4
Product(1)

2 4
1
HBr ; Peroxide effect or addition according to Anti-Markovnikov rule
3
Benzoyl Br
Peroxide Product(2)
17. C

HBr
  +
in CCl4

Br Br

Enantiomers

18. B

HBr 1 equivalent  Br
 
 Br
Thermodynamically
controlled product

19. A

 

More stable because of +M effect of –OMe

MeO

OMe

20. D


HBr
(1 eq) Br



Br

21. B

CH2 HBr CH3  Br 

 Shift
Br

22. A

Br
HBr in CH 3 COOH Na in dry ether
(A) (Wurtz reaction)
(B)

HBr in R O O R Br Na in dry ether

(C) (Wurtz reaction)
(D)
23. ABC

H Br H Br
1,2-additional product
+
(K.C.)
(a) (b)
HBr
CCl4 Br
1,4-additional product + Br
(T.C.)
(a) (b)

a, b  racemic mixture (enantiomeric pair)

a,c  position isomers
c,d  stereoisomers (G.I.)
1. B
Cis-2-butene
Pd/BaSO4
Br2/CCl4 (Anti addition)

(Racemic Mixture)

2. B
CH3–CC–CH2–CH=CH2 Reactivity toward E.A.R b>a

3. D

CH3

H Br

Br2

CCl4
 Br H
 Anti addition
(cis) CH3
(±) Racemic mixture

Addition of Br2 is an electrophilic addition reaction, also stereospecific, stereoselective in nature.

4. B

Br Br
Br

2
CCl
 +
4

Br Br
(meso)

3  streoisomer are possible

5. B
Thermodynamically centrol product is given by 1, 4-addition
+
Br
Br Br

- Br Br
Br
Major
6. C

HO OH
+Cl 2 +H2 O +Cl 2
HC CH HC CH CH CH CH CH Cl
+ Cl +
Cl Cl

+H2O

OH
CH3 Cl CH3
[o] by
HOOC CH OHC CH CH CH
Cl2/H2O -H2O
CH3 Cl CH3
OH

Unstable

7. D

H2 Br2 H Br Br H
Pd-BaSO4 CCl 4 Br H H Br

Threo

Na Br2 H Br
NH3 CCl 4 H Br
trans
erythro

8. D

Br
CH3
Br Br
Br H3C
H3C Br
(minor)

CH3
CH3
Br Br
Br Br
H3C
CH3
(Major)
9. C

10. A
Me Me
H Br H Br
H Br Br H
X= Y=
Br H H Br
H Br H Br

Me Me
Addition of Br2/CCl4 to alkene is an anti-addition reaction
Cis alkene on anti-addition will lead to the formation of threo-isomers

11. BC

Br
2

HO
 Electrophilic addition reaction
2

12. ABCD

13. AC

CH2 CH2 -H
HBr 
CCl4 
3º cation 1º cation
 
Br Br

Br

Br
major

HBr/CCl4
(I)
Major
Br

14. (P)

HBr/R2O 2
(II) Br
hv Major

Positional isomers
Cl
Cl
(Q) 2

(II) hv
(II)
(Different compounds)
OH O

OH
(R) 

(tautomers) (C 3H 6O)
 HBr/CCl4

Br
(Identical)

(S)
HBr/R2O2
hv
Br

15. 9

Br

H2 Br Br
Pd-BaSO4

Br Br

CH3

Br

x=3 y=3
z=6

So y + z = 3 + 6 = 9
1. C

2. D
CH2
O
D 3C C CH
D CD3
7 ‘D’ are incorporated

3. B
HBO
CH3 CH2 CH=O (A)
Major

CH3 C CH

O
OMDM
(B)
CH3 CH3 Major
A and B are functional group isomers.

4. C
Alkene is more reactive towardds electrophilic addition than alkyne.
CH CH2 CH CH2
CH CH2
NaNH2 CH3 I
(1 mol) (1 mol)

C C
C
CH 
C (A)
C
(B)
Me
Br Br
CH CH2
Br 2
(1 mol)

Me

H2/Pd BaSO 4
Br Br
CH CH2

(D)
5. B

HBr (A)
CCl4
Br
Positional isomers

HBr
Br (B)
RO OR

O
Hg(OAc)2
CH 3 CH2 C CH2 (C)
NaBH4

CH 3CH2 C CH Functional isomers

O
B 2H 6
 CH 3 CH 2 CH2 CH (D)
H 2O2/OH

6. D

CH3 CH3 CH3

HBO
Syn +

H H
OH OH

Syn

7. B

8. C

OH H
HO O
HO C CH
C CH3
Kurcherove Tauto
OH C CH Ketone

H OH
HO C CH HO CH2 CH O

Hydroboration Tauto Aldehyde

9. B

aq. H SO

HgSO
2 4

4
 Kucherov 
 reaction 
  OH O

10. A
O O
(A) H C CH3 (B) CH 3 C CH3

O O
(C) CH 3 C CH2 CH3 (D) Ph C CH3

11. A

OH OH O
Hg OAc  2 H O
 2

 
NaBH 4
OH

12. C

13. BC

dil  OH
(A)  H2O
 H 
 1
 3 4
2

(Hydration of alkene with rearrangment)

OH
4
HBO
2
(B)   3 1

Hydration of alkene according to anti-MKR rule without rearrangement.

OH
4
(C) OMDM
  2
3 1

(Hydration of alkene according to MKR rule without rearrangement)

OH

(D) OMDM
 
(Major)
14. BC

(A)
1-Butyne

(B) 2-Butyne

Na
(C) Liq. NH 3

H2
(D)
Pa-BaSO4

Here (A) A and B are position

,

(B) has lower B.P. than

(C) Terminal alkyne react with Na metal due to acidic hydrogen.

Br
(D) 2 Br Meso thats why stereosfecific reaction.

Br

15. (A-P,R,S,T) (B-Q,T) (D-Q,T)

OH
(A) H3O 1, 2H 
  



NBS
(B)   


Br
CH3
H CH3
BH
(C)
2 6
  

 H HO
H2O2 HO BH2 2 2
H  
OH
B
H

HBr 
(D) 
Peroxide
 H Br
Br H
Br
16. 3

conc. H 3PO4
  
OH

+ +

Total 3 products possible

Et

1
SN + E 1
Cl Et

 No rearrangement
(6)

1
SN E1
1. C
Epoxydation reaction

2. A

3. D

(A)

(B)

(C)

4. B

Na/liq. NH3 CH3 H

C==C
H CH3
(Tran-2-butene)
Cold KMnO4(Syn)

Racemic Mixture
5. A
H2/pd-BaSO4 CH3 CH3 Cold KMnO4
C==C meso
H H syn add.
Cis-2-butene

6. D

7. A

CH3

H OH

Cold

KMnO4
H OH
cis-2-butene  Syn addition
CH3

Meso-butane-2,3-diol

8. C

Anti
Trans 
Addition
 Meso, Hence A is trans-2-butene

Syn

Addition


9. B

Symmetry is required for meso product

OH OH

10. C
OH OH

cold alkaline
  = cis-form
KMnO 4 OH OH
cis-cyclohexane-1,2-diol
11. CD

CH3

H Br
Br2

CCl4

(A) + M.I.
cis  Anti Br OH

CH3
(Racemic)

CH3

H Br
2 Br

CCl4

(B)
 
Anti
H Br
(trans)
CH3
(Meso)

CH3

H OH
Cold KMnO4
(C) 
syn
cis H OH

CH3
(Racemic)

Cl
(D) 2

hv Cl + (±)

Cl

12. B
Br2/CCl4  Anti addition on alkene
KMnO4  Syn Addition on alkene
KMnO4
A   1 Product
Hence A must be a symmetrical alkene
B  No product in both cases hence B must very stable compound i.e. benznee

13. D

4 KMnO


KMnO4 is syn addition

Both –OH added will be on same side
Hence products formed will be
 HO HO

HO HO

Total isomers = 4.

14. 3

OH OH

Cold. KMnO4
  +
syn addition

OH OH

Diastereomeric Products (2)

OH OH

Cold. KMnO
4
 
 +

OH OH

Identical compound (1)

1. D
AgNO3
CH3–CH=CH2 
NH OH
 No reaction
4

3 AgNO
CH3–CCH 
NH4 OH
 CH –CCAg (white ppt)
3

2. D

3. C

4. C

CH3 CH3
CH3 CH3
3 differenrt product

CH3 H3C CH3

O O
O , , O O
O
5. C

Cl
H2/Ni +
Cl
C6H14 Only 2 monochloro products
(P)

C6H12 O
O3, Zn
2 moles of
H2 O

6. C

O ,Zn,H O
3
 2
Ozonolysis
 O
O
O
O

O
CH = O
(A) (glyoxal) (B)
CH = O
Acetone

(C) CH 3 C CH O (D) CH3–CH=O

(not a product of this reaction)

7. C

CHO O

 CH3
O

8. A

(A) Two chiral centers and symmetry

(B) No symmetry
 (C) No chiral center

(D) Two products with one chiral center each. Hence, no meso possible.

9. D

(A) CH3–CH=CH2

(B) CH3–CH=CH2

O O
O3
(C) Zn +

(3-pentanone) (2-pentanone)

10. D

O
O O
H
H O +
H H

Not the product we want

11. D

H3C Me
C CH Me
O C O + O Me
H3C 3

H O /Zn Acetald
2 Me
O O Acetone
12. AB
O
Hot. KMnO4 COOH
 +   + CH3COOH

+
 COOH + COOH
O

13. B
List-I
(Products)

(P) (intramolecular Friedal craft acylation)

O
DBE value is 6

(Q) (intramolecular wurtz reaction)

and
(R) (Kolebe’s electrolysis) products are geometrical isomers.
(cis) (trans)

(S) (Diketo product of ozonolysis)

14. 5
CH3 CH3

X=
H3C CH3
cis (+ -)
Number of diastereomer of cis (+ -) are
cis(+ +), (cis (- -), trans (+ +), trans (- -), trans (+ -)

15. 4

NBS NBS


  