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What are the limitations of Hoffman amonolysis of alkyl or aryl halides for preparations of alkyl or aryl amines?

What are the limitations of Hoffman amonolysis of alkyl or aryl halides for preparations of alkyl or aryl amines?

Grade:12th pass

2 Answers

Suraj Prasad IIT Patna
askIITians Faculty 286 Points
5 years ago
Halo alkanes react with alcoholic NH3to form amine . But when halo alkane is in excess, the reaction doesnot stop rather continues till tertiary amine is formed. This continuous ammonolysis is called Hoffman’s ammonolysis.
Limitation :
1) It yields mixture of primary,secondary , tertiary and also a quaternary ammonium salt.

2) Aromatic amines could not be prepared since aryl halides are much less reactive towards nucleophilic substitution reactions.
SHAIK HAFEEZUL KAREEM
109 Points
5 years ago
Halo alkanes react with alcoholic NH3to form amine . But when halo alkane is in excess, the reaction doesnot stop rather continues till tertiary amine is formed. This continuous ammonolysis is called Hoffman’s ammonolysis.Limitation :1) It yields mixture of primary,secondary , tertiary and also a quaternary ammonium salt.2) Aromatic amines could not be prepared since aryl halides are much less reactive towards nucleophilic substitution reactions.

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