CHEMISTRY: ANSWER 1

1. CH3 CH3

Cl
+

Cl
(minor) (major)

CH3 CH3

Br
+

Br
(minor) (major)

CH 2Br

CH 2Cl

2. Br CH CH3

3. CMe 3 CMe 3
Br
(major) + (minor)

Br
CH3

H3C C CH 2Cl

No reaction

S. Bagchi Classes (School of Chemistry) | Salt Lake- CD-293 | Gariahat | 9830705367

CHEMISTRY: ANSWER 2

4. COOH

COOH

No reaction

5. A is i) CrO3/acetic anhydride/H2SO4
ii) H2O/H2SO4
or
i) CrO2Cl2
ii) H2O/H2SO4 (Eterd reaction)
or
i) CAN (Ceric Amnonium nitride)
ii) H+
6. CHO COOH

CHO CH 2OH
i) Concentration NaOH
+
ii) H / H2 O

A B

H 2 SO 4
O O
C
CH 2

O OH +
C OH

CH 2 OH C OH
+
H

CH 2 OH

OH

O
C OH C

O O
CH 2 CH 2

S. Bagchi Classes (School of Chemistry) | Salt Lake- CD-293 | Gariahat | 9830705367

CHEMISTRY: ANSWER 3

7. CHO

Only 1 CH 3 (any one) will react.

CH3

8. 5 > 2 > 3 > 1 > (free radical stability)

9. H3C CH CH CH2

OH
O O

H3C C C CH3

H3C CH CH CH2

OH
10. CH3

CH 3 CH 2 CH CH2 CH 3 CH CH2 H3C C CH CH2 (free radical stability)

CH3

11. O O

H3C C C CH3

12. i) alkaline KMnO4

ii) H+
B → E2 elimination though 30 alcohol.
13. O

H3C C OH + CH 3CH 2 COOH

O O

H3C C C CH 2CH 3

14. Propof’s rule: CH3CH2COOH + CH3CH2COOH

15. O

H3C CH CH CH2CH3

Same

16. O

H3C C CH CH CH CH3

CH3
More reactive (C = C) since free radical most stable at that position.

S. Bagchi Classes (School of Chemistry) | Salt Lake- CD-293 | Gariahat | 9830705367

CHEMISTRY: ANSWER 4

17. O O
CH 3 SH
H3C CH CH CH 2CH 3 H3C CH CHCH 2CH 3

+ SCH 3
H
+
H
H OH
+ H3C CH CH CH 2CH 3
O
SCH 3
CH 3 SH
H3C CH CH CH 2CH 3
(SN 1 like)

OH
H3C CH CH CH 2CH 3

SCH 3

18. CH 3 CH CH 2

OH OH
O

H3C C OH + CO 2 + H2O

19. (a) CH 3 COOH + CO 2 + H2O

(b) CH 3 COOH + CH 3CH 2COOH
O

(c) CH 3COOH + CH 3 C CH 2CH 3

(d) 2(CO 2 + H2O)
O O

(e) H3C C C CH3

O O

(f) CH 3 C C OH
O O

(g) HO C C OH
20. CH 3 CHO + CH 3CH 2CHO
CH 3CHO + CH 3CH 2CHO
CH 3COOH + CH 3CH 2COOH
CH 3COOH + CH 3CH 2COOH
CH 3COOH + CH 3CH 2COOH

S. Bagchi Classes (School of Chemistry) | Salt Lake- CD-293 | Gariahat | 9830705367

CHEMISTRY: ANSWER 5

21. HC CH CH CH CHO

HC CH CH CH COOH + HC CH CH CH CHO
(major)
HC CH CH CH CHO

HC CH CH CH CHO
22. 3 mole of HIO4 is required to break completely.
OH O O OH
OH
H3C CH + CH CH 2 C OH + HO CH CH 2 C CH 2 CH CH 2 CH + HO CH CH3
OH OH
OH OH OH OH

O O OH
O O O O O
H3C C H +H C CH 2 C OH + H C CH 2 C CH 2 CH CH 2 C H+H C CH 3

23. a X
b A, B, C
c A
d A, B, C
e A, B, C

H3C O OH H3C OH OH H3C O

OH HO H

H3C O
H3C CH CH 2 CH 2 COOH
HO H
OH

CH OH CH OH

H3C C O H3C C O CH OH

H3C C OH

COOH CH O

H3C CH OH H3C CH OH

(f) A, B, C
(g) X
(h) A, B, C
(i) X

S. Bagchi Classes (School of Chemistry) | Salt Lake- CD-293 | Gariahat | 9830705367