(s) regarding the following organic…

(s) regarding the following organic transformations.

One or more options correct

Choose the correct statement(s) regarding the following organic transformations.

A. Anisole, on heating with excess concentrated $\mathrm{HI}$ , gives phenol and iodomethane
B. Phenol on reaction with $\mathrm{CHCl_3}$ and aqueous $\mathrm{KOH}$ followed by acidification gives mainly $p$ -hydroxybenzaldehyde
C. Benzamide on treatment with $\mathrm{Br_2}$ and aqueous $\mathrm{NaOH}$ gives aniline
D. Benzenediazonium chloride on treatment with $\mathrm{CuCN}$ gives benzylamine

Show answer and solution

Answer: A, C

(A) Correct. Protonation of the ether oxygen is followed by

S_N2

attack of

\mathrm{I^-}

on the less hindered methyl carbon; the aryl C–O bond does not undergo

S_N2

S_N1

, so phenol and

\mathrm{CH_3I}

result (phenol does not go to iodobenzene). (B) Incorrect. Reimer–Tiemann reaction proceeds through dichlorocarbene attacking the phenoxide mainly at the ortho position, so

o

-hydroxybenzaldehyde (salicylaldehyde) is the major product. (C) Correct. Hofmann bromamide degradation converts

\mathrm{RCONH_2}

into

\mathrm{RNH_2}

with loss of one carbon as carbonate; here

\mathrm{C_6H_5CONH_2\to C_6H_5NH_2}

. (D) Incorrect. The Sandmeyer cyanation replaces

\mathrm{N_2^+}

with CN and gives benzonitrile,

\mathrm{C_6H_5CN}

. Answer: A and C.

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