1.

Write the structure of an isomer of compound 𝐂𝟒𝐇𝟗𝐁𝐫 which is most reactive towards 2016 (OD)
𝑺𝑵𝟏 reaction

2. Write the IUPAC name of the given compound. 2016 (OD)

3. Write the chemical equations involved in the following reactions: 2016 (OD)
(i) Hoffmann-bromoamide degradation reaction
(ii) Carbylamines reaction

4. Write the major product in the following equations: 2016 (OD)

5. Give reasons for the following: 2016 (OD)

(i) Aniline does not undergo Friedal-Crafts reactions.
(ii) (CH3)2NH is more basic than (CH3)3N in an aqueous solution.
(iii) Primary amines have higher boiling point than tertiary amines.
6. How do you convert: 2016 (OD)
(i) Chlorobenzene to biphenyl
(ii) Propene to 1-iodopropane
(iii) 2-bromobutane to but-2-ene
7. Write the major product (s) in the following: 2016 (OD)
i)
 ii)

iii)

8. Write the structure of A and B in the following reaction: 2016 (OD)

(i) 𝐂𝐇𝟑𝐂𝐎𝐂𝐥 𝐇𝟐𝐏𝐝−𝐁𝐚𝐒O𝟒 𝐀 𝐇𝟐𝐍−𝐎𝐇 𝐁

(ii) 𝐂𝐇𝟑𝐌𝐠𝐁𝐫 𝟏.𝐂𝐎𝟐 𝑨 𝐏𝐂𝐥𝟓 𝑩

𝟐. 𝐇𝟑𝐎+

9. Distinguish between: 2016 (OD)

(i) 𝐂𝟔𝐇𝟓 − 𝐂𝐎𝐂𝐇𝟑 𝐚𝐧𝐝 𝐂𝟔𝐇𝟓 − 𝐂𝐇𝐎
(ii) 𝐂𝐇𝟑𝐂𝐎𝐎𝐇 𝐚𝐧𝐝 𝐇𝐂𝐎𝐎𝐇
(c) Arrange the following in the increasing order of their boiling points:
𝑪𝑯𝟑𝑪𝑯𝑶, 𝑪𝑯𝟑𝑪𝑶𝑶𝑯, 𝑪𝑯𝟑𝑪𝑯𝟐𝑶𝑯

10. (a) Write the chemical reaction involved in Wolf-Kishner reduction. 2016 (OD)
(b) Arrange the following in the increasing order of their reactivity towards nucleophilic
addition reaction: 𝐂𝟔𝐇𝟓𝐂𝐎𝐂𝐇𝟑, 𝐂𝐇𝟑 − 𝐂𝐇𝐎, 𝐂𝐇𝟑𝐂𝐎𝐂𝐇𝟑
(c) Why carboxylic acid does not give reactions of carbonyl group.
(d) Write the product in the following reaction.
(e) A and B are two functional isomers of compound C6H6O. On heating with NaOH and
I2, isomer B forms yellow precipitate of iodoform whereas isomer A does not form any
precipitate. Write the formulae of A and B.

11. Out of 𝐂𝐇𝟑 − 𝐂𝐇 − 𝐂𝐇𝟐 − 𝐂𝐥 and 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇 − 𝐂𝐥 ,which is more reactive 2016(D)
| |
𝐂𝐇𝟑 𝐂𝐇𝟑
towards 𝑺𝑵𝟏 Reaction and why?

12. Write the IUPAC name of the given compound: 2016(D)

Br

Br NH2

Br
13. Write the mechanism of the following reaction: 2016(D)
𝟐𝑪𝑯𝟑𝑪𝑯𝟐𝑶𝑯 𝒄𝒐𝒏𝒄. H2SO4 𝑪𝑯𝟑𝑪𝑯𝟐 − 𝑶 − 𝑪𝑯𝟐 – 𝑪𝑯𝟑
𝟒𝟏𝟑𝑲
14. Give reasons: 2016(D)
(i) 𝑪 – 𝑪𝒍 bond length in chlorobenzene is shorter than 𝑪 – 𝑪𝒍 bond length in 𝑪𝑯𝟑 − 𝑪𝒍
(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
(iii) 𝑺𝑵𝟏 reactions are accompanied by racemization in optically active alkyl halides.
15. Write the main product (s) in each of the following reaction: 2016(D)

i)

ii) 𝐶𝐻3 − 𝐶𝐻 = 𝐶𝐻2 (𝑖)𝐵2𝐻6

−
(𝑖𝑖)3𝐻2𝑂2/𝑂𝐻

(iii) 𝐶6𝐻5 – 𝑂𝐻 (𝑖)𝑎𝑞. 𝑁𝑎𝑂𝐻

(𝑖𝑖)𝐶𝑂2, 𝐻+
16. Write the structures of A, B and C in the following: 2016(D)
i) C6H5CONH2 Br2/KOH A NaNO2+HCl B KI C
0-5°C
ii) CH3Cl KCN A LiAlH4 B CHCl3 + KOH C
17. Write the structures of A, B, C, D and E in the following reactions: 2016(D)
C6H6 CH3COCl A Zn-Hg/conc HCl B (i) KMnO4+ KOH C
NaOI (ii) H3O+

D+E
18. (a) Write the chemical equation for the reaction involved in Cannizzaro reaction. 2016(D)
(b) Draw the structure of the semicarbazone of ethanal.
(c) Why pKa of 𝑭 − 𝑪𝑯𝟐 − 𝑪𝑶𝑶𝑯 is lower than that of 𝑪𝒍 − 𝑪𝑯𝟐 − 𝑪𝑶𝑶𝑯?
(d) Write the product in the following reaction
𝑪𝑯𝟑 − 𝑪𝑯 = 𝑪𝑯 – 𝑪𝑯𝟐𝑪𝑵 (𝒊)𝑫𝑰𝑩𝑨𝑳 − 𝑯
(𝒊𝒊)𝑯𝟐𝑶
(e) How can you distinguish between propanal and propanone?