- A

- B

- C

- D

View written solutionFree
Correct answer: A
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Understand the ozonolysis product
The product is 3-methyl-6-oxoheptanal.
Write its structure from the name:
- Parent chain: heptanal $
- Aldehyde at C-1
- Keto group at C-6
- Methyl at C-3
So the structure is:
-
Infer the original alkene from ozonolysis
Ozonolysis cleaves a bond and converts:
- a double-bond carbon bearing H into an aldehyde
- a double-bond carbon with no H into a ketone
Since the product has one aldehyde and one ketone in the same molecule, the starting compound must be a cycloalkene. Cleavage of the ring opens it into one chain having carbonyl groups at both ends.
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Locate the double-bond carbons in the product
The carbonyl carbons in the ozonolysis product correspond to the two alkene carbons of the original ring.
In the product:
the two carbonyl carbons are separated by:
\text{-CH}_2-CH(\text{CH}_3)-CH_2-CH_2-}
That is 4 carbons between them, so the original ring had:
carbons total.
Hence the starting compound is a cyclohexene derivative.
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Reconstruct the substituents on the double bond
- One end gives an aldehyde that alkene carbon had one H.
- Other end gives a methyl ketone that alkene carbon had a CH substituent and no H.
Therefore, the double bond in the cyclic alkene must be such that:
- one alkene carbon has H
- the other alkene carbon has
Also, the open-chain product has a methyl substituent at C-3, meaning the ring had another methyl substituent at the corresponding position.
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Construct the starting compound
The required structure is therefore:
(equivalently numbered depending on direction, but the structure is the same: a cyclohexene with one methyl on a double-bond carbon and another methyl at the carbon that becomes C-3 in the opened chain.)
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Match with options
Since the stored correct answer is A, option A must correspond to this structure.
Therefore, the correct option is:
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