Organic Chemistry 201

Chapter 11   Reactions of Alkyl Halides: Nucleophilic Substitution Reactions

The following are items that you need to know for Exam IV:

SN-2 inversion of configuration - synchronous TS mechanism

SN -1 stepwise mechanism via carbocation intermediate

E-2 anti-coplanar - synchronous TS mechanism

E-1 stepwise mechanism via carbocation intermediate

Nucleophile Nu: -

Leaving groups: - OTs, -I , -Br , -Cl

SN-2 favored by polar aprotic solvents

SN-1 favored by solvents with a high dielectric constant

SN-2 CH3-X > 1° > 2°

SN-1 3° > 2° ~ allylic ~ benzylic

Stereochemistry of SN-2 and E-2 reactions