Question

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 $A$?

• A.
• B.
• C.
• D. $H_2C = O$

Answer 1

Answer: (B)

B is a tertiary alcohol based on given properties.
(a) $CH_2 - \overset{\underset{||}{O}}{C}H_2 + CH_3CH_2MgI \xrightarrow{H_3O^+} $
$\underset{1^{\circ} \text{alcohol}}{CH_3CH_2CH_2CH_2OH}$
(b) $CH_3CH_2\overset{\underset{||}{O}}{C}CH_3 + CH_3CH_2MgI \xrightarrow{H_3O^+} $
$\underset{3^{\circ}\text{alcohol}}{CH_3CH_2\underset{\overset{|}{C}H_3}{\overset{\underset{|}{O}H}{C}}HCH_2CH_3}$
(c) $CH_3CHO + CH_3CH_2 MgI \xrightarrow{H_3O^+} \underset{2^{\circ}\text{alcohol}}{CH_3\underset{\overset{|}{O}H}{C}HCH_2CH_3}$
(d) $HCHO + CH_3CH_2MgI \xrightarrow{H_3O^+} \underset{1^{\circ}\text{alcohol}}{CH_3CH_2CH_2OH}$