Nucleophilic Substitution

Chemistry Level 2

In a reaction between chloromethane C H X 3 C l \ce{CH_3Cl} and hydroxide O H X − , \ce{OH^-}, where would you expect a new coordinate bond to form?

C-O C-H O-Cl H-Cl

Jordan Calmes by Jordan Calmes , 33, USA

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3 solutions

Jordan Calmes
Mar 15, 2016

The final products are methanol C H 3 O H CH_3OH and chloride C l − Cl^- . The chloride anion leaves with an octet of electrons, "stealing" one electron from carbon, and the hydroxide molecule provides a pair of electrons from the oxygen to bond with carbon.

13 Helpful 5 Interesting 6 Brilliant 2 Confused

It is called second order nucleophilic substitution reaction

Angelo De Luca - 5 years, 2 months ago
Tan Yong Boon
Dec 22, 2016

This is a typical bimolecular nucleophilic substitution reaction, in which the halide ion acts as the leaving group and the hydroxide ion acts as the nucleophile. It is evident as the substrate is a halogenomethane and the nucleophile is a strong one (both conditions favouring SN2 mechanism). This problem is a good one as it shows that coordinate bonds do also exist in organic chemistry and not only in inorganic chemistry.

5 Helpful 4 Interesting 3 Brilliant 1 Confused
Rigveda Gupta
Jul 16, 2020

it proceeds like CH3 + HOCl and forms CH4OCl

0 Helpful 0 Interesting 1 Brilliant 2 Confused

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