In a set of reactions acetic acid yielded a product D. CH3COOH SOCl2 A [anhy. AlCl3]benzene B HCN C HOH D The structure of D would be
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Answer
(4) [figure]
Solution
CH3COOH SOCl2 CH3COCl (A, acetyl chloride)
CH3COCl + C6H6 anhy. AlCl3 C6H5COCH3 (B, acetophenone; Friedel–Crafts acylation)
C6H5COCH3 HCN C6H5C(OH)(CN)CH3 (C, cyanohydrin; nucleophilic addition)
C6H5C(OH)(CN)CH3 HOH C6H5C(OH)(CH3)COOH (D)
Hydrolysis converts -CN into -COOH; the phenyl, -OH and -CH3 groups stay on the same carbon.
D is 2-hydroxy-2-phenylpropanoic acid.
Answer: (4)