(a) Write the structures of A, B, C and D in the following reactions:

$\begin{matrix} C H_{3} C N & (i) S n C l_{2} - H C l - -------- \to (i i) H_{2} O A d i l . N a O H - ----- \to & B H e a t - -- \to & C ↓ H C N D \end{matrix}$
(b) Distinguish between:
(i) $C_{6} H_{5} - C H = C H - C O C H_{3}$ and
(ii) $C H_{3} C H_{2} C O O H$ and $H C O O H$
(c) Arrange the following in the increasing order of their boiling points:
$C H_{3} C H_{2} O H, C H_{3} C O C H_{3}, C H_{3} C O O H$

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Solution

(a) $\begin{matrix} A & \to & C H_{3} & - & C H O \end{matrix}$
$\begin{matrix} B & \to & C H_{3} & - & C H & - & C H_{2} & - & C H O | O H \end{matrix}$
$\begin{matrix} C & \to & C H_{3} & - & C H & = & C H & - & C H O \end{matrix}$

(c) $C H_{3} C O O H > C H_{3} C H_{2} O H > C H_{3} C O C H_{3}$

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\begin{matrix} C H_{3} C N & (i) S n C l_{2} - H C l - -------- \to (i i) H_{2} O A d i l . N a O H - ----- \to & B H e a t - -- \to & C ↓ H C N D \end{matrix}

C_{6} H_{5} - C H = C H - C O C H_{3}

C H_{3} C H_{2} C O O H

H C O O H

C H_{3} C H_{2} O H, C H_{3} C O C H_{3}, C H_{3} C O O H

C H_{3} C O C l H_{2}, P d - B a S O_{4} \to A H_{2} N - O H \to B

C H_{3} M g B R 1. C O_{2} - --- \to 2. H_{2} O^{+} A P C l_{5} \to B

C_{6} H_{5} - C O C H_{3}

C_{6} H_{5} - C H O

C H_{3} C O O H

C H_{3} C H O, C H_{3} C O O H, C H_{3} C H_{2} O H

C H_{3} C H_{2} O H, C H_{3} C O C H_{3}, C H_{3} C O O H

Arrange the following compounds in increasing order of their boiling points.

(a) (ii) < (i) < (iii) (b) (i) < (ii) < (iii)

p K_{b}

C_{6} H_{5} N H_{2}, C_{2} H_{5} N H_{2}, C_{6} H_{5} N H C H_{3}

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