- The first step is highly endothermic and has high free energy of activation.
- It involves heterolytic cleavage of the C–Cl bond and there is no other bonds are
formed in this step. - The free energy of activation is about 630 kJ mol–1 (150.6 kcal mol–1) in the gas
phase; the free energy of activation is much lower in aqueous solution –– about
84 kJ mol–1 (20 kcal mol–1).
- It involves heterolytic cleavage of the C–Cl bond and there is no other bonds are
- A free-energy diagram for the SN1 reaction of tert-butyl chloride with water:
Figure 6.7 A free-energy diagram for the SN1 reaction of tert-butyl chloride with
water. The free energy of activation for the first step, ∆G‡(1), is much
larger than ∆G‡(2) or ∆G‡(3). TS(1) represents transition state (1),
and so on.
- The C–Cl bond of tert-butyl chloride is largely broken and ions are beginning to
develop in the transition state of the rate-determining step:
Cδ+
CH 3
CH 3
CH 3 Clδ−