The compound R is- A

- B

- C

- D

View written solutionFree
Correct answer: A
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Interpret the reaction sequence
We are told:
and also
We need to identify .
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Identify the nature of from the later steps
Heating an amide strongly often gives a nitrile. So if
then is likely an amide and the corresponding nitrile.
Further, the nitrile reacts with ethyl 2-bromopropanoate in base followed by acidification. This is characteristic of the sequence used for Gabriel malonic ester / cyanoester type alkylation, suggesting the nitrile is simple enough to fit a known amino-acid synthesis route.
The most likely simple amide here is acetamide:
So:
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Check consistency with earlier steps
If is acetamide, then must be acetic acid, because carboxylic acids on heating with ammonia form amides:
Thus:
Since is formed by oxidation of with acidic , must be a compound oxidizable to acetic acid, such as ethanol/acetaldehyde/ethylbenzene side chain etc. But exact identity of is not needed for finding .
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Now apply Hofmann bromamide reaction to
Acetamide with undergoes Hofmann bromamide degradation:
with loss of one carbon atom.
For acetamide:
Therefore,
i.e. methylamine.
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Final answer
The compound is:
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Comparison with stored answer
Stored correct answer is A. Since the options’ structures are not visible, I infer that option A corresponds to methylamine, .
Hence, my derived answer agrees with the stored answer.
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