Predict the product (T) for the following reaction sequence.
$C_{6} H_{5} - C H = O K C N / O H^{-} - ------ \to R C r O_{2} / H^{\oplus} - ----- \to S (i) c o n c K O H - --------- \to (i i) A c i d i f i c a t i o n T$ :

Cinnamic acid

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Mandelic acid

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Benzilic acid

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Benzoic acid & Benzyl alcohol

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Solution

The correct option is C Benzilic acid
This is an example of Benzil-benzilic acid rearrangement. Benzaldehyde reacts with $K C N$ in an alkaline medium to form benzaldehyde cyanohydrin.
Oxidation with acidified chromium trioxide gives benzil. Treatment with conc KOH followed by acidification gives rearranged product benzillic acid.

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Similar questions

Find the Relative molar masses of

(a) Benzyl Alcohol $C_{7} H_{8} O$

(b) Acetic acid $(C H_{3} C O O H)$

C_{6} H_{5} - C H = C H - C H_{3} + C C l_{4} \to

C_{6} H_{5} - C H_{2} C O_{2} C H_{3} 1. C H_{3} M g B r (e x c e s s) - ------------ \to 2. H_{2} O

K M n O_{4} / H O^{-} / H e a t

S_{N} 1

C_{6} H_{5} - C | H C H_{3} - B r

C_{6} H_{5} - C H_{2} - B r

C_{6} H_{5} - C | H C H_{3} - I

C_{6} H_{5} - C H_{2} - I

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