CHAPTER 8

ORGANIC HALOGEN COMPOUND

NOMENCLATURE

Factor influencing the reaction Mech. SN1 vs SN2
1)

Carbocation stability SN1: 3o > 2o > 1o > CH3X

SN2: 3o < 2o < 1o < CH3X

3o form stable carbocation SN2 reaction doesn’t occur in 3o Steric effect - in SN2, Nuc attack the saturated C bonds and pushed out the halide ion. For a brief time, 5 gps coordinated-crowded. -In SN1, C loses a halide ion to form trivalent carbocation – less crowded
Crowding increases, SN1 increases

Alkyl halides:

3o

2o

1o CH3X

Crowding decreases, SN2 increases

3) Strength of the nucleophile - SN2 – nuc replace the halide -Charged Nucs are stronger than nuetral. (OH- > HOH; RO- > ROH)

4) Solvent Polar solvent (water and alcohols) can solvate the halide ion Promote the SN1 process that involves stable formation of carbocation and halide ion. 5) Leaving Group - Good leaving group F- < Cl- < Br- < I-

When there are 2 non-identical beta carbons????????

Zaitsev’s rule: In the elimination of HX
from an alkyl halide, the more highly substituted alkene product predominates

The difference between E1 and E2 reactions ???

Substitution Vs Elimination
Elimination increases 3o 2o 1o Substitution decreases Preparation of the ether –Williamson Synthesis