B(3 - oxo - hexanedicarboxylic acid) X will be :-- A

- B

- C

- D

View written solutionFree
Correct answer: C
- Interpret the information given
We are told that hydrocarbon :
- is unsaturated,
- absorbs two molecules of hydrogen on catalytic hydrogenation.
This means has a total of two units of pi-bond unsaturation that can be hydrogenated. So could contain:
- two double bonds, or
- one triple bond, etc.
Also, on reaction, it gives 3-oxo-hexanedicarboxylic acid.
Let us write the structure of 3-oxo-hexanedicarboxylic acid.
Hexanedicarboxylic acid means a 6-carbon chain including two terminal carboxyl groups:
This is 3-oxo-hexanedioic acid.
- Recognize the reaction type
Formation of a dicarboxylic acid with a ketone group in the middle strongly suggests oxidative cleavage of an unsaturated hydrocarbon.
For cyclic unsaturated hydrocarbons:
- cleavage of a double bond opens the ring,
- each alkene carbon becomes:
- a carboxylic acid if it had at least one H,
- a ketone if it had no H.
We need a product:
This indicates that after ring cleavage:
- both ends are carboxylic acids,
- one internal carbon becomes a ketone.
- Infer the structure of
Since the product has 6 carbons and is a dicarboxylic acid formed by ring opening, is likely a cycloalkene/cycloalkadiene derivative.
Because absorbs 2 moles of , it must contain two hydrogenatable pi bonds.
A suitable structure is cyclohex-2-enone equivalent hydrocarbon precursor is not possible, because is a hydrocarbon only. So the oxygen in the product must arise during oxidative cleavage.
To obtain one ketone in the chain, one of the double-bond carbons in the original hydrocarbon must be fully substituted (no H), so on oxidation it gives ketone.
A well-known structure matching this pattern is 1-methylcyclopentadiene / methylenecyclopentene-type system, but we must also satisfy the 6-carbon dicarboxylic acid product.
The product
is obtained from oxidative cleavage of 1,3-cyclohexadiene with one appropriate substitution pattern. The hydrocarbon that fits both:
- hydrogenation consuming ,
- oxidative cleavage giving 3-oxo-hexanedioic acid,
is the structure corresponding to option C.
- Why option C fits
Option C must be the cyclic diene whose oxidative cleavage produces:
and which consumes exactly two moles of hydrogen.
Thus the correct choice is:
- Comparison with stored answer
Stored correct answer = C.
Our derived answer also = C, so they agree.
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