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Preparation of Carboxylic Acids

A neutral org...

Question

A neutral organic compound A has formula $C_{9} H_{16} O_{3}$ and rotates plane polarized light. A on acid hydrolysis produces B and $C (C_{3} H_{8} O)$ . C on partial oxidation with PCC gives $D (C_{3} H_{6} O)$ which does not give iodoform test. D on treatment with dilute solution of $N a O H$ gives $E (C_{6} H_{12} O_{2})$ which is diastereomeric. E on treatment with the acidic solution of $K M n O_{4}$ produces B. Deduce structures of A to E.

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Solution

Ester compound on hydrolysis gives alcohol(in this case $p r o p a n - 1 - o l$ ) and Acid.
$P C C$ (pyridinium chlorochromate) will convert or oxidize the primary alcohol into aldehyde
Aldol condensation will give finally the aldol product.

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