Nitrogen Containing Compounds Question 142

Question: A nitrogen containing organic compound gave an oily liquid on heating with bromine and potassium hydroxide solution. On shaking the product with acetic anhydride, an antipyretic drug was obtained. The reactions indicate that the starting compound is [KCET 2004]

Options:

A) Aniline

B) Benzamide

C) Acetamide

D) Nitrobenzene

Show Answer

Answer:

Correct Answer: B

Solution:

$ C_6H_5CONH_2+Br_2+KOH\to C_6H_5CONHBr+KBr+H_2O $ $ \downarrow KOH $ $ K_2CO_3+C_6H_5NH_2\xleftarrow[2,KOH]{}C_6H_5NCO+KBr+H_2O $ $ C_6H_5NH_2+{{(CH_3CO)}_2}O\to CH_3\underset{\begin{smallmatrix} Acetanilide \\ ( antipyretic ) \end{smallmatrix}}{\mathop{CONHC_6H_5}},+CH_3COOH $