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JEE Main levelOne or more correct optionsDifficulty 2 of 3co194

Which of the following correctly give propanoic acid (after acidification where needed)?

A $CH X_{3} CH X_{2} MgBr$ + dry $CO X_{2}$ , then $H X_{3} O X^{+}$
B $CH X_{3} CH X_{2} CN$ boiled with dilute $H X_{2} SO X_{4}$
C $CH X_{3} CH X_{2} OH$ treated with $NaBH X_{4}$
D $CH X_{3} CH X_{2} COOCH X_{3}$ heated with aqueous $NaOH$ , then acidified

Answer: A, B, D

The Grignard route, the nitrile hydrolysis and the ester hydrolysis give propanoic acid.

CH X_{3} CH X_{2} MgBr + CO X_{2}

gives

CH X_{3} CH X_{2} COOMgBr

and then the acid; nitrile hydrolysis keeps the carbon count; and the ester gives propanoic acid. Ethanol with

NaBH X_{4}

gives no reaction.

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