Answer Key + Solution

Balaji

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Answer Key + Solution

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DPP # 1

I. (1) (2) (3) (4)

(5) (6)PhOH

Ph(7)

Ph OH

Ph Ph(8)

Ph

OH

(9) (10)

OH

Ph (11)OH CH3

(12)OH

(13)HO

(14) x = 5 (15) 4

(16) 5

DPP # 2

(a)OHH OHH

Ph HO

r1 > r2 > r3

(b) CH3CH2OH,OHH

r1 > r2

(c)

H OH

NO2

r3 > r1 > r2

(d)HO

Ph

H HO Phr1 > r2 > r3

(e)H Ph

OH

OH Ph

HO Ph

r1 > r2 > r3 > r4

(f) OHPh OHPh No reaction r1 > r2 > r3

Answer Key + Solution


DPP # 3

(1)OH Ph

PhPh(2)

OH Ph

PhPh(3) +

PhPh

O (4)

OH Ph

PhPh

(5)OH Ph

PhPh(6)

PhPh

O(7)

(8) Ph – CH3 (9) Ph – Br

10. (a)O

MgBr

H O3

;O

H O3

EtMgBr

O

H O3

MgBr

(b) H O3

MgBrO

;H O3

MgBrCHO

(c)

O

CH3 CD3

CT MgBr3

H O3

;

O

CH3 CT3

CD MgBr3

H O3

O

CD3 CT3

CH MgBr3

H O3

11. (a) 7 (b) 8

DPP # 4(a) 3º alcohol (b) 3º alcohol (c) 3º alcohol (d) 3º alcohol (e) 3º alcohol (f) 3º alcohol (g) 3º alcohol

(h) 3º alcohol (i) ketone (j) 2º alcohol (k) 2º alcohol (l) 3º alcohol (m) 3º alcohol (n) alkane

(o) No reaction (p) 3º alcohol (q) 2º alcohol (r) No reaction (s) alkane (t) No reaction (u) 3º alcohol

(v) ketone (w) 3º alcohol (x) 3º alcohol (y) 3º alcohol (z) 2º alcohol


DPP # 5

1. A 2. D 3. D 4. C 5. C 6. D 7. A8. A 9. C 10. B11. (A) R, (B) Q, (C) S, (D) S 12. Due to acidic hydrogen

13. (a) + CH4 + MgBr2 (b)

BrPh||

CHCCH 22 (c)

14. (a) (b)

OH OH

(c) (d)

OH

CH3

CH3

DPP # 61. 4 2. 4 3. 5 4. 4 5. 2 6. 3 7. 38. 4 9. 2 10. 2 11. 4 12. 7 13. 2 14. 415. 2

DPP # 7

I. (i)

OHPh

(A)

Ph

(B)

BrPh

(C)

(ii)

OH

H(A)

(B) (major)

Br

(minor)Br

(iii) H

OH

H(A)

(B)

major

major

Br

+

Brminor

(iv) EtOH

(v)

OHCH3

(A)

(B)

OO

(C)

(vi) Ph

OH(vii)

MgBr

(A)

Ph

OH

HPh

(B)

Ph – C – Ph||O

(C)(viii)

Ph – CH – Ph|OH


(ix)

Benzene

(x) |C

OH

(xi) CH4

II. (i)

OH

EtEt (ii) OH (iii) (Ph)3C – OH (iv) OHPh

OHPh

(v) OH

PhPh Ph +

OHHO(vi)

OH

PhPh Ph(vii) (Ph)3 C – OH (viii)

Ph PhPh

OH

(ix) Ph Ph

OH

+ EtSH (x) (Ph)3 C – OH (xi) (Ph)3 C – OH

DPP # 8I. (i) a > b, a > b (ii) b > a, b > a (iii) a > b, a > b (iv) a > b > c, a > b > c

(v) a > b, a > b (vi) a > b > c, a > b > c (vii) a > b, a > b (viii) b > a, b > a(ix) c > b > a , c > b > a (x) a > c > b , a > c > b (xi) a > b , a > b(xii) b > a, b > a (xiii) a > b, a > b (xiv) a > b, a > b (xv) b > a, b > a

DPP # 9

(a)NH2

(b)H

O(c) OH (d) CH3CH2OH

(e) No Reaction (f) NH2(g)

H

OD

H

(h)H

OH

H (i)H

OH

D (j) (Me) CHCH CH CH2 2 2

||O

(k) N (l)

OH

(m) N

CH3

(n)

OH

OH (o) O

OH

OH

(p)OH

+ CH OH3


(q)

OH

and

OH

(r)

OH

OH +

OH

(s)

O

OMe

HO

(t)

O

OEt

OH

(u)

OH

OH OH(v)

SH

(w) CH3OH (x) CH3CH2OH (y)OH D

DPP # 101. C 2. D 3. A

4. (1)

N – OH..

(2)

N – NH2

(3)

R – N – R

(4) Ph – CH = N – OH

(5)

N – NH – CONH2

(6) N – NH

NO2

NO2

(7)

O

NH2CH3

(8) CH – C – NH – CH33

O

(9) O

NHNH2

(10) C = N – NH2

|Et

(11) CH – CH3 |

|ONa

C CH(12) Ph – CH = N – PH (13) Orange ppt

(14)

OHCN

(A)

OH

(B)

NH2

O

(C)

(15)

OHCH3

5. (1) Step-I :

N

H

N+

Resonance stabalised carbocation

Step-II : N+

..OH2

....

N +..

OH2 base

Acid N+

OH2

....HO – H

NH

+

O


(2) H

O

HO

H H

OH

HO....

+

OH

O+ H

–H+

OCH3+

OCH OH3

..

..O

OH2

O

+

(3)

O

O

NH3

.. O

O–

NH3+ Acid-base

reactionO

OH

NH2

..

HO OH

N|H

–H O2

N|H

(4) Br Br

..

.. .. CH NH3 2

..Br NH–CH3

H–HBr

N|CH3

(5) Step-I :

O.. .. SO H3– O–

SO H3

Step-II :

O–

SO H3

Na

ONa

SO H3

(6)..

CH – Cl3

.... 2

3SN

NH CH3NH2 ClCH3 CH3 – NH – CH3 2

3SN

ClCH CH – N – CH3 3|

CH3

..

CH – N – CH3 3|

|CH3

CH3

+ CH Cl3

Mechanism of this reaction is SN2.


DPP # 11

1. (a)N

(b)

O

N

(c)NN

(d) NN

Ph

Ph

(e)NN

(f)N

N

(g) O CH = N – NH NO2

NO2

(h)

NOH

2. (a)

CHO

CH – OH

CN

(b) CN

OH

||O

(c) OH

CN

N

O

(d) C – CH CH – C – CH2 2 3

O OH

CN

(e) ||O

CN

OH

H(f)

OH

CN HH

3. (e)

4. (a) O

+ NH2OH (b)

O

C – H + H N2

(c) N + OH2 (d)

NH2

+ O (e) CHO + NH OH2

(f)

O

+ NH2NH2 (g) O + H2NOH (h) ||O

+ H2NOH

(i) CH3

NH2

O

(j) NH2

O (b) H2/Ni/LiAlH4


DPP # 12

1. PhCH2CH2CH2COOH 2.

OHCH3

3.

4. Ph–CH2–CH3 5.

CH2CH3

NH2

6. Ph – CH2CH3

7. 8. CH –CH –CH –COOH22 2 9.

10.

CH2

11. Me(–CH2)5–CH3 12.O

DPP # 13

1. Wolf-kishner 2. 3.

O O

,

O

4.

CH CH2 3

Cl

;

CH CH2 3

OH

5.

CH3

OH

6.

DPP # 14

(i) (ii) (iii) (iv)

CH3

MeO

MeO


DPP # 15

I. (1) (A)

OCH|||

HCCHCHCHCH|OH

3

23 (B)

OCH|||

HCCCHCHCH

3

23

(2) (C)

O OH

(3) (D)

OOH|||

HCCHCHCHPh|Ph

2

(4) (E)

O OH

(F)

O

(5) (G)

OOH|||

PhCCHCPh|

CH

2

3

(H)

O||

PhCCHCPh|

CH3

II. (1) (A) HO

O

(B)

O

(2) (C)

CH3 OHC—CH3

O

(3) (D)

CH3

OH

O

(4) (E)

O

OH(F)

O

(5) (G)

CH3

C—CH3

OIII. Excluding Stereo Including Stereo

(1) 4 12(2) 2 4(3) 4 6(4) 6 16(5) 4 12

(1)*

CHOCHCHMe|

OH

2 = 2

3CHOH||

CHOCHCHMe**

= 4


OH|

CHOCHCHEt *2 = 2

3CHOH||

CHOCHCHEt ** = 4

(2)*

CHOCHCHPh|

OH

2 = 2*

CHOCHCHMe|

OH

2 = 2

(3)*

CHOCHCHCH|

OH

23 = 2

3

23

CH|

CHOCHCCH|

OH

= 1

3

323

CH|

COCHCHCCH|

OH

= 1

*COCHCHCHCH

|OH

323 = 2

(4)

3

33

CH|*

COCHCHCHCH *|OH

= 4*

CHOCHCHCH|

OH

23 = 2

332

33

CHCHCH||*

COCHCH———CCH *|OH

= 4*

CHCOCHCHCH|

OH

323 = 2

32

3223

CHCH*|

CHCOCHCHCHCH|

OH

= 2

32

23

CHCH*|

CHOCHCCH|

OH

= 2

(5)

3

3

CH|*

COCHCHCHPh *|OH

= 4

*CHCOCHCHCHPh

|OH

322 = 2

Et*|

EtCOCHCMe|OH

2 = 2

3

3

CHEt||*

COCH–CH—CMe *|OH

= 4

IV. (1)

||

||

O

O(2)

O||

CHCCH 33


V. (1) (A)

C – H||O

CH – CH – C – H2 2 ||O

(B) C – H||O

(2)CH—C H6 5

O(3) A =

||O

CH3

B =

O||

HCCH3

(4) 3223 CHCCHCHCCH||||OO

(5) CHOCHCHCHCCH||O

2223 VI. (C)

DPP # 161. D 2. B 3. D 4. A 5. A 6. B 7. C8. D

9.

O

O + H C–OD3H 10.

O

O + DCH OD2D

11.

O

OH(i) Ph–CH OH + 2 12. Ph – CH – C – O|OH

|O|

13.

CH OH2

O N–C–CH OH2 2

CH OH2

DPP # 17The compounds which give positive iodoform test are :

(1), (5), (7), (10), (13), (16), (20), (21), (23), (24), (25), (27), (28), (29), (30), (31), (32), (34), (37), (38) (39),

(41), (42), (43), (46), (47), (48), (49).

Answer Key + Solution

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