free radical halogenation

Problem # 1280

The structure of 2-methylbutane is shown below.

a) Draw the structures of all possible monochloro products resulting from the free-radical chlorination of 2-methylbutane.

b) Based on statistics alone, what do you expect the major product to be? Is this the same structure as the expected major product? Explain.

c) How would the relative yield of the products differ if bromine was used instead of chlorine?

MS 899 - Beginning Mechanism Practice Submitted by Matt on August 6, 2011.

Textbook and Chapters: Carey and Giuliano 8th Ed. (2010), Chapters 4, 5

Keywords: carbocation rearrangement, free radical halogenation, mechanism

Description: Practice mechanisms from the first half of Fall semester orgo. Dehydration (E1), substitution with carbocation rearrangement (SN1), and free-radical bromination.

Total Problems: 3

Problem # 722

Show how to prepare vinyl benzene from benzene.

Problem # 346

For the reaction below, draw the structures of the radical intermediate and the final product.

Problem # 324

Using curved hooks, draw a mechanism for the free radical bromination  reaction shown below.