- A

- B

- C

- D

View written solutionFree
Correct answer: B
- Use the molecular formula to find unsaturation
Given compound has formula .
Degree of unsaturation:
So, has one degree of unsaturation.
- Interpret the 2,4-DNP test
A positive 2,4-dinitrophenylhydrazine test indicates the presence of a carbonyl group (), so is either an aldehyde or a ketone.
- Interpret the Tollens test
gives a negative Tollens test, so it is not an aldehyde. Therefore, must be a ketone.
- Use optical activity condition
is stated to be optically active, so it must contain at least one chiral carbon.
Thus we need a compound with:
- formula
- a ketone functional group
- at least one chiral center
- Find a suitable ketone isomer
Acyclic saturated ketones with formula are possible. We need one having a stereogenic center.
A suitable structure is:
This is 3-methyl-2-pentanone.
Check chirality at the carbon : It is attached to four different groups:
Hence this carbon is chiral, so the compound is optically active.
- Conclusion
Therefore, must be 3-methyl-2-pentanone, which corresponds to option B.
- Comparison with stored answer
Stored correct answer is B. My derived answer is also B, so they agree.
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