Question #46a17

1 Answer
May 22, 2017

The #"S"_text(N)1# mechanism involves racemization, which is 50 % retention of configuration and 50 % inversion of configuration.

Explanation:

Inversion of configuration

Inversion of configuration is a process in which the configuration of a stereocentre changes.

Usually, an #R# configuration changes into #S#, and #S# changes into #R#.

An example is the #"S_text(N)2# reaction of 2-bromobutane with sodium iodide.

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Racemization

Racemization is a process in which a chiral substrate is converted into a mixture in which there is 50 % retention and 50 % inversion of configuration.

An example is the #"S"_text(N)1# reaction of a tertiary substrate,

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The reaction proceeds through a planar, achiral carbocation intermediate in which nucleophilic attack is equally probable from either side.