Organic chemistry

1. MAHARSHI DAYANAND UNIVERSITY
ROHTAK
ORGANIC CHEMISTRY II
PRESENTATION ON : REACTION OF AROMATIC AMINE WITH
GRIGNARD REAGENT AND
CARBYLAMINE REACTION

2. REACTION WITH GRIGNARD REAGENT
• Amino conpounds react with grignard reagent to produce hydrcarbon.
• Amines are having acidic hydrogen with them as hydrogen is directly attached with
highly electronegative N atom. R- of Grignard reagent reacts with acidic H of the
reactant and gives hydrcarbon.
EXAMPLE :

3. REACTION WITH CHLOROFORM OR
CARBYLAMINE REACTION
• Primary aromatic amines react with ethanolic
potassium hydroxide and chloroform to form
carbylamines or isonitriles which have a disagreeable
odour.
Example :

4. • The first step is the dehydrohalogenation (removal of hydrogen halide from
a given substrate) of chloroform to give dichlorocarbene intermediate. This
dichlorocarbene intermediate is very reactive.
• The electrophilic dichlorocarbene attacks the nucleophilic nitrogen of the
primary amine. The elimination of the hydrochloric acid leads to the
formation of isonitrile.
MECHANISM

5. REFERENCES
• Advanced organic chemistry . Arun Bahl B.S. Bahl 2012 edition pg no. 1123
and 1128.
• https://byjus.com/chemistry/carbylamine-reaction-mechanism/
• https://www.quora.com/How-do-Grignard-reagents-react-with-
amine#:~:text=Grignard’s%20reagent%20reacts%20with%20primary,lack%2
0of%20hydrogen%20on%20nitrogen.&text=Grignard%20reagent%20reacts
%20with%20Amine,secondary%20Amines%20have%20acidic%20hydrogen
%20.

6. THANK YOU