An organic acid P $C_{11} H_{12} O_{2}$ can easily be oxidized to a dibasic acid which reacts with ethylene glycol to produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products. P undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes another set of reactions to produce S.

The compound R is :

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Solution

The correct option is A

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The structure of the carbonyl compound P, which gives positive iodoform test undergoes reaction with MeMgBr followed by dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R, which undergoes intramolecular aldol reaction to give predominantly S.

The structure of the carbonyl compound P is:

Q. A carbonyl compound P, which gives positive iodoform test, undergoes reaction with MeMgBr followed by dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R, which undergoes intra-molecular aldol reaction to give predominantly S.

The structure of the carbonyl compound P, is

Q. A carbonyl compound P, which gives positive iodoform test, undergoes reaction with MeMgBr followed by dehydration to given an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R, which undergoes intramolecular-aldol reaction to give predominantly S.

P = 1. M e M g B r - --------------- \to 2. H^{+}, H_{2} O 3. H_{2} S O_{4} / h e a t Q 2. O_{3} / Z n - H_{2} O - -------- \to R O H^{-} - -- \to h e a t S

The structure of the carbonyl compound P, is

Q. A carbonyl compound P (from i-iii), which gives positive iodoform test, undergoes with MeMgBr followed by dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R, which undergoes intramolecular aldol reaction to give predominantly S.

2. Product S is :

P = 1. M e M g B r - --------------- \to 2. H^{+}, H_{2} O 3. H_{2} S O_{4} / h e a t Q 2. O_{3} / Z n - H_{2} O - -------- \to R O H^{-} - -- \to h e a t S

The structure of the product S, is

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