The structure of the product S is- A

- B

- C

- D

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Correct answer: B
- Identify carbonyl compound from iodoform test
A compound gives positive iodoform test if it contains either:
- a methyl ketone group, , or
- an alcohol oxidizable to it.
Since is itself a carbonyl compound, the relevant possibility is that is a methyl ketone:
- Reaction with followed by dehydration
Methylmagnesium bromide adds a methyl group to the carbonyl carbon of the ketone:
On dehydration, this tertiary alcohol gives an alkene . The most natural alkene formed is:
So is an alkene having one end as and the other alkene carbon attached to and .
- Ozonolysis of
For an alkene of type ozonolysis cleaves the double bond to give:
- formaldehyde from the terminal
- a carbonyl compound from the substituted carbon:
But the question says ozonolysis gives a dicarbonyl compound (single molecule containing two carbonyl groups), which then undergoes intramolecular aldol reaction.
Therefore, the group in must itself contain another carbonyl in such a way that after ozonolysis, the product is a diketone/keto-aldehyde capable of cyclization.
The suitable starting methyl ketone is:
This is a carbonyl compound and contains the methyl ketone unit, so it gives iodoform test.
- Addition of and dehydration
For attacks the ketone carbonyl preferentially to give:
Dehydration gives:
- Ozonolysis of
Cleavage of gives:
- from terminal
- and the substituted carbon becomes a carbonyl:
Thus the dicarbonyl compound obtained is: which is a keto-aldehyde.
- Intramolecular aldol reaction of
Now consider:
The enolate forms at the methyl ketone side, and intramolecular attack occurs on the aldehyde carbonyl. This gives the most favorable six-membered ring.
Cyclization leads to a β-hydroxy ketone, which under aldol conditions predominantly dehydrates to the conjugated product :
This is the standard predominant product from intramolecular aldol condensation of
- Match with options
Hence the correct structure is the option corresponding to:
So the correct option is:
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