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In a set of reactions propionic acid yielded a compound D. CH3CH2COOH → SOCl2 → B → NH3 → C → KOH → D

1. CH3CH2CONH2
2. CH3CH2NHCH3
3. CH3CH2NH2
4. CH3CH2CH2NH2

Correct answer: CH3CH2CH2NH2

Solution

Propionic acid reacts with SOCl2 to form CH3CH2COCl (B). Reaction with NH3 gives CH3CH2CONH2 (C), which upon Hoffmann bromamide degradation with KOH forms CH3CH2CH2NH2 (D).

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