Question:medium

Reaction of butanone with methylmagnesium bromide followed by hydrolysis gives:

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To quickly find the product of a Grignard reaction: Formaldehyde gives \(1^\circ\) alcohols, other Aldehydes give \(2^\circ\) alcohols, and Ketones always give \(3^\circ\) alcohols.
Updated On: Apr 20, 2026
  • 2-methyl-2-butanol
  • 2-butanol
  • 3-methyl-2-butanol
  • 2,2-dimethyl-1-butanol
  • 2-pentanol
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The Correct Option is A

Solution and Explanation

Step 1: Understanding the Concept:
The question asks for the product of a Grignard reaction.
A Grignard reagent (\(\text{RMgX}\)) acts as a strong nucleophile and attacks the electrophilic carbonyl carbon of a ketone or aldehyde.
Reacting a ketone with a Grignard reagent followed by acid hydrolysis always yields a tertiary alcohol.
Step 2: Key Formula or Approach:
The general mechanism involves:
1. Nucleophilic Addition: \(\text{R}_1-\text{C}(=\text{O})-\text{R}_2 + \text{R}_3\text{MgX} \rightarrow \text{R}_1-\text{C}(\text{O}^-\text{MgX}^+)(\text{R}_3)-\text{R}_2\)
2. Hydrolysis: \(\text{R}_1-\text{C}(\text{O}^-\text{MgX}^+)(\text{R}_3)-\text{R}_2 \xrightarrow{\text{H}_3\text{O}^+} \text{R}_1-\text{C}(\text{OH})(\text{R}_3)-\text{R}_2 + \text{Mg}(\text{OH})\text{X}\)
Step 3: Detailed Explanation:
The starting material is butanone, a 4-carbon ketone with the structure \(\text{CH}_3-\text{C}(=\text{O})-\text{CH}_2-\text{CH}_3\).
The Grignard reagent is methylmagnesium bromide (\(\text{CH}_3\text{MgBr}\)). The methyl group (\(\text{CH}_3^-\)) acts as the nucleophile.
The methyl carbanion attacks the carbonyl carbon of butanone, breaking the \(\pi\)-bond and pushing electrons onto the oxygen to form an alkoxide intermediate:
\[ \text{CH}_3-\text{C}(=\text{O})-\text{CH}_2-\text{CH}_3 + \text{CH}_3\text{MgBr} \rightarrow \text{CH}_3-\text{C}(\text{O}^-\text{MgBr}^+)(\text{CH}_3)-\text{CH}_2-\text{CH}_3 \]
Subsequent hydrolysis with water and an acid catalyst protonates the alkoxide oxygen:
\[ \text{CH}_3-\text{C}(\text{O}^-\text{MgBr}^+)(\text{CH}_3)-\text{CH}_2-\text{CH}_3 \xrightarrow{\text{H}_2\text{O}/\text{H}^+} \text{CH}_3-\text{C}(\text{OH})(\text{CH}_3)-\text{CH}_2-\text{CH}_3 \]
Now, we determine the IUPAC name of the product.
The longest carbon chain containing the \(-\text{OH}\) group has 4 carbons (butane).
Numbering from the left gives the lowest locant for the \(-\text{OH}\) group, placing it at position 2.
There is also a methyl substituent at position 2.
Therefore, the name is 2-methyl-2-butanol.
Step 4: Final Answer:
The final product is 2-methyl-2-butanol.
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