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Synthetic Dyes

An aromatic c...

Question

An aromatic compound 'A' on heating with $B r_{2}$ and $K O H$ forms a compound 'B' of molecular formula $C_{6} H_{7} N$ which on reacting with $C H C l_{3}$ and alcoholic $K O H$ produces a foul smelling compound 'C'. Write the structures and IUPAC names of compounds A,B and C .

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Solution

When benzamide reacts with $B r_{2} / K O H$ Hoffmann bromamide degradation reaction will take place to form aniline and when aniline is treated with $C H C l_{3} / K O H$ carbylamine reaction will take place to form phenyl isocyanide
$∴$ $A : B e n z a m i d e$
$B : A n i l i n e$
$B : P h e n y l i s o c y n a i d e$

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B r_{2}

K O H

C_{6} H_{7} N

C H C l_{3}

K O H

A

B

B r_{2}

K O H

C

C_{6} H_{7} N

A, B

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An aromatic amine (A) was treated with alcoholic potash and another compound (Y) when foul smelling gas

was formed with formula C₆H₅NC. Y was formed by reacting a compound (Z) with Cl₂ in the presence of

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C_{6} H_{5} N C

C l_{2}

C_{6} H_{5} N C .

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