- A

- B

- C

- D

View written solutionFree
Correct answer: A
-
Given molecular formula and Tollens' test
Compound has formula and gives a positive test with .
Hence, must contain an aldehyde group. -
Triacetate formation with acetic anhydride
On treatment with acetic anhydride, gives a triacetate derivative.
This means contains three hydroxyl groups that can be acetylated. -
Possible nature of
With one aldehyde group and three groups in a four-carbon compound, must be an aldo-tetrose: This matches . -
Given that the L-isomer of is considered
Among aldotetroses, the possibilities are:- erythrose
- threose
-
Reaction with bromine water
Bromine water oxidizes the aldehyde group to a carboxylic acid, giving an aldonic acid.
The product is said to be optically active. -
Reaction with
Nitric acid oxidizes both terminal groups:So the product becomes a dicarboxylic acid:
Product is said to be optically inactive.
-
Identify which aldotetrose gives meso tartaric acid on oxidation
Oxidation of erythrose gives: with the two middle groups on the same side in Fischer projection for one enantiomeric series, which corresponds to meso tartaric acid after considering symmetry. Hence it is optically inactive.Oxidation of threose gives an optically active tartaric acid, not inactive.
Therefore, must be erythrose.
-
Check consistency with bromine water product
Oxidation of erythrose with bromine water gives erythronic acid, which remains optically active, matching the statement about . -
Conclusion
Therefore, compound is L-erythrose (or simply erythrose as the compound type). -
Comparison with stored answer
The stored correct answer is A, and this matches the identified compound.
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