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Freidel Craft Alkylation Acylation

An organic co...

Question

An organic compound 'A', $C_{8} H_{6}$ on reacting with dil $H_{2} S O_{4}$ and $H g S O_{4}$ gives a compound 'B' which can also be obtained from reaction of benzene with acid chloride in the presence of anh. $A l C l_{3}$ . Compound 'B' when reacted with iodine and aq. NaOH yields 'C' and a yellow compound 'D' . Identify A to D with proper justification.

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Solution

Given that the compound $B$ can also obtained by reaction between benzene with acid chloride in presence of anhy. $A l C l_{3}$ .
The reaction can be given as follow:
$C_{6} H_{6} B e n z e n e + C H_{3} C O C l a n h y . A l C l_{3} - ------ \to C_{6} H_{5} - O | | C - C H_{3} a c e t o p h e n o n e (B)$
Also, compound $B$ is also obtained by reaction of compound $A$ with $H_{2} S O_{4}$ and $H g S O_{4}$ .
This reaction is hydration of alkyne which give aldehyde and ketones on rearrangement.
Thus the compound $A$ must be alkyne.
Looking at product $B$ , it can be concluded that the compound $A$ will be $C_{6} H_{5} - C \equiv C H$ which is $1 - p h e n y l e t h y n e$
Now, the compound $B$ is acetophenone i.e. a methyl ketone. Thus it can react with $I_{2} + N a O H$ to undergo Haloform reaction to give sodium benzoate( $C$ ) and yellow coloured Iodoform( $D$ )
$C_{6} H_{5} - O | | C - C H_{3} B I_{2} + N a O H - ----- \to C_{6} H_{5} - O | | C - O N a C + C H I_{3} D$

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