Thermodynamic and Kinetic Control

Consider the following two reactions:

Reaction A

Li Br

Reaction B Br

NaI I

1.! Propose the most likely mechanism for each reaction. Include a diagram of the transition state leading to each intermediate or product.

Reaction A:

Reaction B:

2.! Explain why Reaction B is reversible, while Reaction A is not.

Revise your mechanisms if necessary to include equilibrium arrows where appropriate.

Thermodynamic and Kinetic Control

Reaction A Li Br 95% yield

Reaction B Br

NaI I 69% yield

3.! Draw a labeled reaction coordinate energy diagram for Reaction A. To the extent possible, prepare your diagram to scale.

4.! To the same graph (above), add an energy diagram for Reaction B. At each step of the mechanism, be sure to consider the relative energies of the two reaction pathways.

5.! For Reaction C, shown below, how would the energy diagram be different than that for Reaction B? Draw a rough, overlay sketch below to support your answer.

NaCl Br Cl 21% yield