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JEE Advanced levelSingle correct optionDifficulty 3 of 3g3101

2-Diazo-1-phenylethanone, $C X_{6} H X_{5} - CO - CHN X_{2}$ , is heated with $Ag X_{2} O$ in methanol. The main organic product is

AMethyl 3-phenylpropanoate
B1-Phenylethanone
CMethyl benzoate
DMethyl 2-phenylethanoate, $C X_{6} H X_{5} CH X_{2} COOCH X_{3}$

Answer: D

Loss of

N X_{2}

gives the keto-carbene

C X_{6} H X_{5} - CO - CH :

. Wolff rearrangement moves the phenyl group from the carbonyl carbon to the carbene carbon and gives the ketene

C X_{6} H X_{5} - CH = C = O

. Methanol adds across

C = O

of the ketene to give the ester

C X_{6} H X_{5} CH X_{2} COOCH X_{3}

.

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