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Which of the following reaction will NOT give primary amine as the product?
medium
Amines
2023
chemistry
C H 3 C O N H 2 → B r 2 / K O H {CH}_3{CONH}_2 \xrightarrow{Br_2 / KOH} C H 3 CON H 2 B r 2 / K O H Product
C H 3 C N → ( i i ) H 3 O + ( i ) L i A l H 4 {CH}_3CN \xrightarrow[(ii) H_3O^+]{(i) LiAlH_4} C H 3 CN ( i ) L i A l H 4 ( ii ) H 3 O +
C H 3 N C → ( i i ) H 3 O + ( i ) L i A l H 4 {CH}_3NC \xrightarrow[(ii) H_3O^+]{(i) LiAlH_4} C H 3 NC ( i ) L i A l H 4 ( ii ) H 3 O +
C H 3 C O N H 2 → ( i i ) H 3 O + ( i ) L i A l H 4 {CH}_3CONH_2 \xrightarrow[(ii) H_3O^+]{(i) LiAlH_4} C H 3 CON H 2 ( i ) L i A l H 4 ( ii ) H 3 O +
Explanation To solve this problem, we need to analyze each reaction to determine if it produces a primary amine.
\newline Let's examine each option step-by-step:
\newline • Option 1: C H 3 C O N H 2 → B r 2 / K O H {CH}_3{CONH}_2 \xrightarrow{Br_2 / KOH} C H 3 CON H 2 B r 2 / K O H
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Product
Product
Product
Product
This is the Hofmann bromamide degradation reaction.
• In this reaction, an amide is converted to a primary amine with one less carbon atom.
• The product is
C H 3 N H 2 , CH_3NH_2, C H 3 N H 2 , which is a primary amine.
• Option 2:
C H 3 C N → ( i i ) H 3 O + ( i ) L i A l H 4 {CH}_3CN \xrightarrow[(ii) H_3O^+]{(i) LiAlH_4} C H 3 CN ( i ) L i A l H 4 ( ii ) H 3 O + Product
This involves the reduction of a nitrile using
L i A l H 4 . LiAlH_4.
\newline L i A l H 4 . • The nitrile is reduced to a primary amine.
• The product is
C H 3 C H 2 N H 2 , CH_3CH_2NH_2, C H 3 C H 2 N H 2 , which is a primary amine.
• Option 3:
C H 3 N C → ( i i ) H 3 O + ( i ) L i A l H 4 {CH}_3NC \xrightarrow[(ii) H_3O^+]{(i) LiAlH_4} C H 3 NC ( i ) L i A l H 4 ( ii ) H 3 O + Product
This involves the reduction of an isocyanide (isonitrile).
• The reduction of an isocyanide typically leads to the formation of a secondary amine.
• Therefore, the product is not a primary amine.
• Option 4:
C H 3 C O N H 2 → ( i i ) H 3 O + ( i ) L i A l H 4 {CH}_3CONH_2 \xrightarrow[(ii) H_3O^+]{(i) LiAlH_4} C H 3 CON H 2 ( i ) L i A l H 4 ( ii ) H 3 O + Product
This involves the reduction of an amide using
L i A l H 4 . LiAlH_4.
\newline L i A l H 4 . • The amide is reduced to a primary amine.
• The product is
C H 3 C H 2 N H 2 , CH_3CH_2NH_2, C H 3 C H 2 N H 2 , which is a primary amine.
Conclusion:
• Option 3 does not produce a primary amine; it produces a secondary amine.
Therefore, the correct answer is Option 3.