Advices For Studying Organic Chemistry

Relative reactivity 200,000 5,000 2,800 1,300 6.6 1

6.14D SOLVENT EFFECTS ON SN 1 REACTIONS:

THE IONIZING ABILITY OF THE SOLVENTS

1. Polar protic solvent will greatly increase the rate of ionization of an alkyl halide
   in any SN1 reaction.

1. Polar protic solvents solvate cations and anions effecttively.


2. Solvation stabilizes the transition state leading to the intermediate carbocation
   and halide ion more it does the reactants ⇒ the free energy of activation is
   lower.


3. The transition state for the ionization of organohalide resembles the product
   carbocation.

(H 3 C) 3 C Cl (H 3 C) 3 Cδ+ δ−Cl (CH 3 ) 3 C+ + Cl−

Reactant Transition state Products
Separated charges are developing

2. Dielectric constant: a measure of a solvent’s ability to insulate opposite charges
   from each other.