When 3,4-dimethyl-2,4-hexadiene reacts with one equivalent of HBr, 2 products are formed.

1) Draw the 1,2-addition product and the mechanism for its formation.
2) Draw the 1,4-addition product and the mechanism for its formation.
3) Which of these products is the kinetic and which is the thermodynamic?
How to promote the formation of the thermodynamic product?

Question

When 3,4-dimethyl-2,4-hexadiene reacts with one equivalent of HBr, 2 products are formed.

1) Draw the 1,2-addition product and the mechanism for its formation.
2) Draw the 1,4-addition product and the mechanism for its formation.
3) Which of these products is the kinetic and which is the thermodynamic?
How to promote the formation of the thermodynamic product?

| Organic Chemistry 2

Accepted Answer

3)

Kinetic Product:
Product from the fastest reaction (best intermediate - most substituted carbocation)

Thermodynamic Product:
Most stable product (most substituted alkene). Favored by high temperature and long time

Midterm 1 - Question 3 | Organic Chemistry 2

Organic Chemistry 2 - Midterm 1