IMAT 2014 Q51 [Organic Molecules]

The reaction scheme below shows some reaction conversions of organic molecules.

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Which is the correct combination of process and compounds for this scheme?

A. process T: reduction; compound W: ester; compound X: amide
B. process T: reduction; compound W: ketone; compound X: nitrile
C. process T: oxidation; compound W: ester; compound X: amide
D. process T: reduction; compound W: ketone; compound X: amide
E. process T: oxidation; compound W: ester; compound X: nitrile

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Process T is an oxidation reaction; when you oxidize a primary alcohol, a carboxylic acid should be formed.

We can hence narrow down our answer to C or E.

Both options state the obvious, which is that the reaction between a carboxylic acid and alcohol should form an ester (Compound W).

The differentiation should be at the reaction of ammonia and a carboxylic acid. Here, Compound X is an amide.

When adding alcohol to a carboxylic acid, it forms an ester.

When adding ammonia to a carboxylic acid, it forms an amide.

The answer is therefore, C.

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