Identify the product obtained when following acid prolonged heating.
$P H - O | | C - C H_{2} - O | | C - O H$

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Solution

It is a beta keto acid, which undergoes decarboxylation on heating via a six membered ring intermediate.

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P h - N H - O H

P h - C H O

H - O | | C - O H

O H | C H_{2} - O | | C - C H_{3}

C H_{2} = O H | C - C H_{2} - O | | C - C H_{3} ⇌ C H_{3} - O | | C - C H_{2} - O | | C - C H_{3} ⇌ C H_{3} - O H | C = C H - O | | C - C H_{3}

I

I I

I I I

C H_{2} = O H | C - C H_{2} (I) - O | | C - C H_{3} ⇌ C H_{3} - O | | C - C H_{2} (I I) - O | | C - C H_{3}

⇌ C H_{3} - O H | C = C H (I I I) - O | | C - C H_{3}

C H_{3} - C H_{2} - O | | C - O H P C l_{3} - -- \to N H_{3} - -- \to Δ O B r^{⊖} - -- \to

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