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Author Question: Explain Walden inversion. ... (Read 48 times)

CharlieWard

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on: Aug 23, 2018
Explain Walden inversion.

Question 2

Why is cyclohexylamine more reactive than aniline when the former reacts with methyl bromide?


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manuelcastillo

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Reply #1 on: Aug 23, 2018
Answer to Question 1

During an aliphatic nucleophilic substitution by SN2 mechanism, a complete inversion in stereochemistry of a particular structure takes place. This stereochemical outcome is called Walden inversion. One such example is the conversion of L-malic acid into D-chlorosuccinic acid.

Answer to Question 2

-NH2 is a poor leaving group, but it is a good nucleophile because of the presence of lone pairs. The reaction between cyclohexylamine or aniline and methyl bromide helps in the formation of N-methylamines via an SN2 mechanism. Howev


CharlieWard

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Reply 2 on: Aug 23, 2018
Thanks for the timely response, appreciate it

nyrave

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Reply 3 on: Yesterday
Great answer, keep it coming :)

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