Question:

An optically active compound [X] (Molecular formula \( C_8H_{11}N \)) reacts with \( CHCl_3/ \) Ethanolic KOH on heating to form an isocyanide. On reaction with \( NaNO_2/HCl \), it yields an alcohol with liberation of \( N_2 \). Identify the compound [X].

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Carbylamine test confirms primary amine, while reaction with nitrous acid giving alcohol and \( N_2 \) indicates primary aliphatic amineCheck optical activity by identifying a chiral carbon.
Updated On: May 6, 2026
  • 2-Ethylaniline.
  • 1-Phenylethanamine.
  • 3,4-Dimethylaniline.
  • 2,4-Dimethylaniline.
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The Correct Option is B

Solution and Explanation

Step 1: Use the carbylamine test.
The compound reacts with \( CHCl_3 \) and ethanolic KOH on heating to form an isocyanide.
This is the carbylamine reaction, which is given only by primary amines.
Therefore, compound [X] must be a primary amine.

Step 2: Use reaction with nitrous acid.

The reagent \( NaNO_2/HCl \) generates nitrous acid \( HNO_2 \) in situ.
Primary aliphatic amines react with nitrous acid to give alcohols with liberation of nitrogen gas.
The reaction is:
\[ RNH_2 + HNO_2 \rightarrow ROH + N_2 + H_2O \]

Step 3: Check optical activity.

The compound [X] is optically active, so it must contain a chiral carbon atom.
\( 1\text{-Phenylethanamine} \) has the structure:
\[ C_6H_5-CH(NH_2)-CH_3 \]
The carbon attached to \( C_6H_5 \), \( NH_2 \), \( CH_3 \), and \( H \) has four different groups, so it is chiral and optically active.

Step 4: Verify molecular formula.

For \( 1\text{-Phenylethanamine} \):
\[ C_6H_5-CH(NH_2)-CH_3 \]
The molecular formula is:
\[ C_8H_{11}N \]
This matches the given molecular formula.

Step 5: Check other options.

2-Ethylaniline, 3,4-dimethylaniline, and 2,4-dimethylaniline are aromatic amines but they do not have a chiral carbon atom.
Also, aromatic primary amines with \( NaNO_2/HCl \) form diazonium salts rather than directly giving alcohol with liberation of \( N_2 \) under the same condition.

Step 6: Conclusion.

Thus, the compound [X] is \( 1\text{-Phenylethanamine} \).
Therefore:
\[ \boxed{1\text{-Phenylethanamine}} \]
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