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Organic Nitrogen Compounds — Chemistry STD 12 — Question

Tamilnadu BoardEnglish MediumSTD 12ChemistryOrganic Nitrogen Compounds5 Marks
Question
An aromatic compound 'A' on treatment with aqueous ammonia and heating forms compound 'B' which on heating with $Br _2$ and KOH forms a compound ' C ' of molecular formula $C _6 H _7 N$. Write the structures and IUPAC names of compound $A , B$ and C .
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Answer

Step - 1: To find out the structure of compounds ' B ' and ' C '.
1. Since compound ' C ' with molecular formula $C _6 H _7 N$ is formed from compound ' B ' on treatment with $Br _2+ KOH$ (i.e., Hoffmatm bromamide reaction). Therefore, compound ' B ' must be an amide and ' C ' must be an amine. The only amine having the molecular formula $C _6 H _7 N$ is $C _6 H _5 NH _2$ (i.e., aniline or benzenamine).
2. Since ' C ' is aniline, therefore, the amide from which it is formed must be benzamide $\left( C _6 H _5 CONH _2\right)$. Thus, compound ' B ' is benzamide. The chemical equation showing the conversion of ' B ' to ' C ' is
Image
To find out the structure of compound ‘A’. Since compound ‘B’ is formed from compound ‘A’ by treatment with aqueous ammonia and heating. Therefore, compound ‘A’ must be benzoic acid or benzenecarboxylic acid.Image

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