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Answer by Chakravarthy Kalyan for SN2 reactions and inversion of configuration in compounds with more than one chiral centre

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Here I have a compound with 2 chiral centers. There is only inversion at Carbon with iodine undergoing $\mathrm{S_N2}$ reaction. The second carbon does not undergo $\mathrm{S_N}$ reaction. There is no change in its configuration.

Example 1

nucleophillic substitution

In the example below ,

enter image description here

[Ref : https://en.chem-station.com/reactions-2/2016/05/neighboring-group-participation.html]

before a nucleophile attacks externally, OH of carboxylic group attacks internally via $\mathrm{S_N2}$. The 3 membred ring opens via another $\mathrm{S_N2}$ attack by hydroxide ion. The net result is retention of configuration .

Example 2

In this example , two chilral carbons are at neighboring carbons. As explained earlier , Sulphur attacks internally via $\mathrm{S_N2}$ attack. Again bromide ion attacks via another $\mathrm{S_N2}$ leading to retention of configuration ( Anchimeric assistance ).

NUCLEOPHILLIC SUBSTITUTION

[Ref : http://www.chem.ucla.edu/~harding/IGOC/A/anchimeric_assistance.htmll]

Example 3

This example also behaves similarly to one discissed above.enter image description here

[Ref: Molecules 11(4):212-8 • April 2006  DOI: 10.3390/11040212 ]

In conclusion,

  • If there exists no lone pair donating group at neighboring carbon to leaving group, then $\mathrm{S_N2}$ attack takes place with inversion of configuration (Example 1).

  • If there exists a lone pair donating group (Example 2 and Example 3)at neighboring carbon to leaving group, then retention of configuration is seen.


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