What is C in the following reaction sequence? | vedclass

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(B) $1$. The starting material is $3-(hydroxymethyl)cyclohexan-1-ol$. $2$. Treatment with $PCC$ (Pyridinium chlorochromate) oxidizes both the primary

Vedclass · Accepted Answer

$3-$formyl$-1-$methylcyclohexan$-1-$ol

Vedclass · Answer

(B) $1$. The starting material is $3-(hydroxymethyl)cyclohexan-1-ol$. $2$. Treatment with $PCC$ (Pyridinium chlorochromate) oxidizes both the primary and secondary alcohol groups to a ketone and an aldehyde,respectively,forming $3-formylcyclohexan-1-one$ $(A)$. $3$. The aldehyde group is more reactive towards nucleophilic attack than the ketone. However,the reaction uses $1 \ eq$ of ethylene glycol $(HO-CH_2-CH_2-OH)$ with $H^+$,which selectively protects the aldehyde as an acetal,leaving the ketone free. $4$. Reaction with $CH_3MgBr$ (Grignard reagent) occurs at the ketone carbonyl to form a tertiary alcohol after workup. $5$. Finally,acid-catalyzed hydrolysis $(H_3O^+)$ of the acetal group regenerates the aldehyde. $6$. The final product $C$ is $3-formyl-1-methylcyclohexan-1-ol$.

What is $C$ in the following reaction sequence?

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