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NEET CHEMISTRYMedium

Which one of the following on reduction with LiAlH4 yields a secondary amine?

A

Methyl isocyanide

B

Acetamide

C

Methyl cyanide

D

Nitroethane

Step-by-Step Solution

Lithium aluminium hydride (LiAlH4LiAlH_4) is a strong reducing agent that affects nitrogen-containing functional groups differently:

  1. Isocyanides (RNCR-NC): Reduction yields secondary amines (RNHCH3R-NH-CH_3). Specifically, methyl isocyanide (CH3NCCH_3NC) is reduced to dimethylamine (CH3NHCH3CH_3-NH-CH_3), which is a secondary amine .
  2. Amides (RCONH2R-CONH_2): Reduction yields primary amines (RCH2NH2R-CH_2-NH_2). Acetamide (CH3CONH2CH_3CONH_2) gives ethylamine .
  3. Cyanides/Nitriles (RCNR-CN): Reduction yields primary amines (RCH2NH2R-CH_2-NH_2). Methyl cyanide (CH3CNCH_3CN) gives ethylamine .
  4. Nitroalkanes (RNO2R-NO_2): Reduction yields primary amines (RNH2R-NH_2). Nitroethane gives ethylamine .

Therefore, only Methyl isocyanide yields a secondary amine.

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