Organic Chemistry - Nucleophilic Substitution Reactions

NUCLEOPHILIC SUBSTITUTION REACTIONS

Organic Chemistry| SN1 and SN2 Nucleophilic Substitution	Nucleophilic Substitution: Nucleophiles in SN2 & SN1 Reactions
Nucleophilic Substitution: SN2 & SN1 Reactions and Stereochemistry	SN1 and SN2 reactions. When do they take place at a saturated carbon atom?
Solvent Effects and SN2 and SN1 reactions: Nucleophilic Substitution	The SN2 reaction: Substitution Nucleophilic Bimolecular

 

Nucleophilic Substitution reactions occur when an electron rich species the nucleophile reacts at an electrophilic saturated carbon C atom attached to an electronegative group, the leaving group, that can be displaced as shown below:

As electron pair donors, nucleophiles must either contain an unshared electron pair that is easily available or they must contain a bonding electron pair that can be donated from the bond involved and thus be made available to the electrophile. From this it follows that nucleophiles are usually anions or neutral species.

Nucleophilic substitution reactions are an important class of reactions that allow the interconversion of functional groups. Of particular importance are the substitution reactions of alkyl halides (R-X) and alcohols (R-OH).

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References

1. R. Bruckner, “Advanced Organic Chemistry – Reaction Mechanisms”, 2nd Edition, Elsevier, 2002

2. M.B. Smith & J. March “March’s Advanced Organic Chemistry”, 6th Edition, Wiley-Interscience, 2007

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