SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

6. STEREOCHEMISTRY OF SN2 REACTION

Transition state
(Penta-coordinated)

Inversion of configuration
(Walden Inversion)
NOTE:
SN2 reaction completes with 100% inversion of configuration.
SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

SN 2

Leaving group --- wedge

Nucleophile ---dash
Leaving group --- dash
Nucleophile --- wedge
SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

To create inversion product in Fischer

projection replace leaving group by
SN 2 nucleophile and exchange any one pair

SN 2
 SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

7. Reactivity towards SN2 reaction

Branching at beta
position decreases
rate of SN2
 SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

NOTE:
Allyl and benzyl halide shows SN2 reaction in good amount.

(Allyl halide) (Benzyl halide)

shows SN2 reaction in excellent amount

Rate towards SN2 reaction

 SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

8. SN2 reaction does not take place in

Vinyl halide

Aryl halide

Neopentyl halide
NOTE :
SN1 and SN2 reaction does not take place at sp2 hybridized carbon atom
 SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

Compare the rate towards SN2 reaction

SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)
 SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)

MECHANISM
1st step :

2nd step :
SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)

CHARACTERISTICS
1. It is a two step reaction.
2. Kinetics of reaction

ROR  lkyl halide]

3. Rate is independent of concentration of nucleophile.

4. Carbocation intermediate is formed. Rearrangement may be possible.
5. SN1 reaction is favoured by polar protic solvent (Ex. H2O, ROH )

Helps in ionizing bond.

Helps in stabilization of charges.
 SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)

6. STEREOCHEMISTRY OF SN1 REACTION

Retention product

ENANTIOMERS
Inversion product
(Nu occupies a
NOTE: position opposite to
Theoretically , racemic mixture must be formed that of leaving
but inversion product dominates over retention product. group)
Partial racemization takes place.
More the stability of carbocation, more will be racemization.

(contact ion pair)

 SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)

7. Reactivity towards SN1 reaction  stability of carbocation intermediate

If leaving group is different then R-I > R-Br > R-Cl > R-F

8. SN1 reaction does not take place in

Bredt’s rule violation

Vinyl halide Aryl halide

 SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)

Compare rate towards SN1 reaction

SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)
SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)