- A()3 – C –
- B
- C

- D

View written solutionFree
Correct answer: D, B
- Identify the nature of compound [A
Since [A has molecular formula and on hydrolysis gives a carboxylic acid [B and an alcohol [C, [A must be an ester:
So:
- [B = acid part from the ester
- [C = alcohol part from the ester
Also, oxidation of [C with gives [B.
This means the alcohol [C must oxidize to the same carboxylic acid [B.
That is only possible when [C is a primary alcohol of the form:
So the ester must be of type:
where hydrolysis gives:
- acid:
- alcohol:
and oxidation of gives the same .
- Check Option A
Option A is:
Hydrolysis gives:
- Acid [B: (pivalic acid)
- Alcohol [C: (neopentyl alcohol)
Now oxidize neopentyl alcohol:
So alcohol oxidizes to the same acid obtained on hydrolysis.
Hence Option A is possible.
- Check Option B
Option B is:
Hydrolysis gives:
- Acid [B: (butanoic acid)
- Alcohol [C: (1-butanol)
Oxidation of 1-butanol gives:
This is the same acid as formed in hydrolysis.
Hence Option B is also possible.
- General condition for possible esters
For ester , after hydrolysis:
- acid =
- alcohol =
For oxidation of alcohol to give same acid, we need:
Thus ester must be:
So any option where alkoxy part is not a primary alcohol corresponding to the same carbon skeleton as the acid part will be not possible.
- Using the given stored correct answer and analysis
From direct checking, A and B are possible. Therefore the structures not possible must be the remaining correct options among the list, i.e. C and D if they were present.
However, the stored correct answer says D, B. This conflicts with the clear analysis because B is definitely possible:
which matches the acid obtained from hydrolysis of option B.
So the stored answer appears inconsistent.
Because options C and D are not visible in the prompt, I can only conclude with certainty that B is not among the impossible structures and A is possible.
Thus the stored answer including B is incorrect.
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