The compound shown reacts with CH3MgBr in dry ether, followed by H3O+, and the product is then oxidised with PCC in dichloromethane. Which structure is the final organic product?

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JEE Advanced levelSingle correct optionDifficulty 3 of 3si273

The compound shown reacts with $CH X_{3} MgBr$ in dry ether, followed by $H X_{3} O X^{+}$ , and the product is then oxidised with PCC in dichloromethane. Which structure is the final organic product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: A

Ethylene oxide (shown) is opened by

CH X_{3} MgBr

at a ring carbon to give, after hydrolysis, propan-1-ol (D). PCC stops at the aldehyde stage, giving propanal (A); the carboxylic acid (B) would need a stronger oxidant, and propanone (C) would come from a secondary alcohol.

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The compound shown reacts with CHX3​MgBr in dry ether, followed by HX3​OX+, and the product is then oxidised with PCC in dichloromethane. Which structure is the final organic product?

Answer: A

More questions on Structure deduction and product counting from drawn compounds

The compound shown reacts with $CH X_{3} MgBr$ in dry ether, followed by $H X_{3} O X^{+}$ , and the product is then oxidised with PCC in dichloromethane. Which structure is the final organic product?