An organic compound $B$ is formed by the reaction of ethyl magnesium iodide with a substance $A$ , followed by treatment with dilute aqueous acid. Compound $B$ does not react with PCC or PDC in dichloromethane. Which of the following is a possible compound for $A$ ?

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

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

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C H_{3} O | | C H

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H_{2} C = O

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Solution

The correct option is B $C H_{3} C H_{2} O | | C C H_{3}$
$B$ is a tertiary alcohol based on given properties.
(a) $C H_{2} - C H_{2} + C H_{3} C H_{2} M g I H_{3} O^{+} - -- \to C H_{3} C H_{2} C H_{2} C H_{2} O H 1^{o} alocohol$

(b) $C H_{3} C H_{2} O | | C C H_{3} + C H_{3} C H_{2} M g l H_{3} O^{+} - -- \to C H_{3} C H_{2} O H | C H | C H_{3} C H_{2} C H_{3} 3^{o} alcohol$

(c) $C H_{3} C H O + C H_{3} C H_{2} M g l H_{3} O^{+} - -- \to C H_{3} C H C H_{2} C H_{3}$
$|$
$α$ - Carban atom $O H$
$2^{o}$ alcohol

(d) $H C H O + C H_{3} C H_{2} M g l H_{3} O^{+} - -- \to C H_{3} C H_{2} C H_{2} O H 1^{o} alcohol$

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An organic compound B is formed by the reaction of ethyl magnesium iodide with a substance A, followed by treatment with dilute aqueous acid. Compound B does not react with PCC or PDC in dichloromethane. Which of the following is a possible compound for A?

An organic compound $B$ is formed by the reaction of ethyl magnesium iodide with a substance $A$ , followed by treatment with dilute aqueous acid. Compound $B$ does not react with PCC or PDC in dichloromethane. Which of the following is a possible compound for $A$ ?