Which of the following compounds does not give alcohol on reaction with RMgX?

The reactions of Grignard reagents ($R-MgX$) with various types of compounds under specific conditions. Here's the analysis and explanation:

Reaction with Oxygen ($O_2$$O$$2$​) and $H^+$$H$$+$:

• The Grignard reagent reacts with oxygen to form a hydroperoxide intermediate, which upon acid hydrolysis yields an alcohol ($R-OH$).

• General Reaction: $R-MgX + O_2 + H^+ \rightarrow R-OH$.

  Reaction with Aldehydes ($R-CHO$$R$$-$$CHO$):

• The Grignard reagent reacts with aldehydes to form a secondary alcohol ($R-CH(OH)-R$).

• General Reaction: $R-MgX + R'-CHO \xrightarrow{H^+} R-CH(OH)-R'$

  Reaction with Formaldehyde ($H-C=O$$H$$-$$C$$=$$O$):

• The Grignard reagent reacts with formaldehyde to form a primary alcohol ($R-CH_2OH$).

• General Reaction: $R-MgX + HCHO \xrightarrow{H^+} R-CH_2OH$

  Reaction with Ketones ($R-CO-R'$$R$$-$$CO$$-$$R$$\prime$):

• The Grignard reagent reacts with ketones to form tertiary alcohols ($R-CR'(OH)-R''$).

• General Reaction: $R-MgX + R'-CO-R'' \xrightarrow{H^+} R-C(OH)(R')-R''$

  Reaction with Epoxides ($\text{Cyclopropane Oxygen Ring}$$Cyclopropane\; Oxygen\; Ring$):

• The Grignard reagent opens the epoxide ring, forming an alcohol. The $R$ group from the Grignard reagent adds to the less substituted carbon atom of the epoxide.
• General Reaction: $R-MgX + \text{Epoxide} \xrightarrow{H^+} R-CH_2-CH_2OH$