Question:
Identify the major product from the following reaction sequence
Identify the major product from the following reaction sequence
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The Hell-Volhard-Zelinsky reaction brominates the \(\alpha\)-carbon of carboxylic acids using:
\[
Br_2/\text{Red }P
\]
Updated On: Jun 25, 2026
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The Correct Option is A
Solution and Explanation
Step 1: Oxidation with PCC.
The given alcohol is a primary alcohol attached to cyclopentane ring: Cyclopentyl ethanol PCC oxidizes primary alcohol into aldehyde: \[ R-CH_2OH \xrightarrow{PCC} R-CHO \] Thus, cyclopentane acetaldehyde is formed.
Step 2: Oxidation with Tollen's reagent.
Tollen's reagent oxidizes aldehydes into carboxylic acids in alkaline medium.
\[ R-CHO \xrightarrow{[O]} R-COOH \] After acidification: \[ R-COOH \] is obtained.
Thus, cyclopentane carboxylic acid is formed.
Step 3: Reaction with \(Br_2\) and red phosphorus.
This is the Hell-Volhard-Zelinsky \((HVZ)\) reaction.
Carboxylic acids containing: \[ \alpha\text{-hydrogen} \] undergo bromination at the \(\alpha\)-carbon.
\[ R-CH_2COOH \xrightarrow{Br_2/Red\ P} R-CHBrCOOH \]
Step 4: Hydrolysis.
Hydrolysis retains the brominated carboxylic acid structure.
Hence, the final product is: \[ \alpha\text{-Bromocyclopentane carboxylic acid} \]
Step 5: Final conclusion.
Therefore, the major product formed is \[ \boxed{\alpha\text{-Bromocyclopentane carboxylic acid}} \]
The given alcohol is a primary alcohol attached to cyclopentane ring: Cyclopentyl ethanol PCC oxidizes primary alcohol into aldehyde: \[ R-CH_2OH \xrightarrow{PCC} R-CHO \] Thus, cyclopentane acetaldehyde is formed.
Step 2: Oxidation with Tollen's reagent.
Tollen's reagent oxidizes aldehydes into carboxylic acids in alkaline medium.
\[ R-CHO \xrightarrow{[O]} R-COOH \] After acidification: \[ R-COOH \] is obtained.
Thus, cyclopentane carboxylic acid is formed.
Step 3: Reaction with \(Br_2\) and red phosphorus.
This is the Hell-Volhard-Zelinsky \((HVZ)\) reaction.
Carboxylic acids containing: \[ \alpha\text{-hydrogen} \] undergo bromination at the \(\alpha\)-carbon.
\[ R-CH_2COOH \xrightarrow{Br_2/Red\ P} R-CHBrCOOH \]
Step 4: Hydrolysis.
Hydrolysis retains the brominated carboxylic acid structure.
Hence, the final product is: \[ \alpha\text{-Bromocyclopentane carboxylic acid} \]
Step 5: Final conclusion.
Therefore, the major product formed is \[ \boxed{\alpha\text{-Bromocyclopentane carboxylic acid}} \]
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