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 introduces halogen at the \(\alpha\)-position of carboxylic acids having \(\alpha\)-hydrogen.
Updated On: Jun 24, 2026
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The Correct Option is D
Solution and Explanation
Step 1: Oxidation of primary alcohol.
The given compound contains a primary alcohol group.
In the presence of \[ CrO_3/H_2SO_4, \] primary alcohol is oxidized to carboxylic acid.
Thus, \[ RCH_2OH \rightarrow RCOOH \]
Step 2: Formation of carboxylic acid.
The side chain attached to cyclohexane is converted into the corresponding carboxylic acid.
So, the intermediate formed is cyclohexyl propanoic acid.
Step 3: Reaction with \(Cl_2/\text{Red P}\).
Carboxylic acids having an \(\alpha\)-hydrogen undergo Hell-Volhard-Zelinsky reaction with \[ Cl_2/\text{Red P} \] This introduces chlorine at the \(\alpha\)-carbon of the carboxylic acid.
Step 4: Hydrolysis step.
On hydrolysis, \[ H_2O \] converts the intermediate acyl halide derivative back into the \(\alpha\)-chloro carboxylic acid.
Therefore, the major product is: \[ \alpha\text{-chloro cyclohexyl propanoic acid} \]
Step 5: Final conclusion.
Hence, the major product is option (4).
\[ \boxed{\text{\(\alpha\)-chloro cyclohexyl propanoic acid}} \]
The given compound contains a primary alcohol group.
In the presence of \[ CrO_3/H_2SO_4, \] primary alcohol is oxidized to carboxylic acid.
Thus, \[ RCH_2OH \rightarrow RCOOH \]
Step 2: Formation of carboxylic acid.
The side chain attached to cyclohexane is converted into the corresponding carboxylic acid.
So, the intermediate formed is cyclohexyl propanoic acid.
Step 3: Reaction with \(Cl_2/\text{Red P}\).
Carboxylic acids having an \(\alpha\)-hydrogen undergo Hell-Volhard-Zelinsky reaction with \[ Cl_2/\text{Red P} \] This introduces chlorine at the \(\alpha\)-carbon of the carboxylic acid.
Step 4: Hydrolysis step.
On hydrolysis, \[ H_2O \] converts the intermediate acyl halide derivative back into the \(\alpha\)-chloro carboxylic acid.
Therefore, the major product is: \[ \alpha\text{-chloro cyclohexyl propanoic acid} \]
Step 5: Final conclusion.
Hence, the major product is option (4).
\[ \boxed{\text{\(\alpha\)-chloro cyclohexyl propanoic acid}} \]
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