Chemistry 104 A/D Discussion: Alkene Halogenation & Arrow Pushing - Prof. Christian R. Ray, Exams of Chemistry

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Chemistry 104 A/D Discussion Section Worksheet Discussion Section #

Key Ideas from Lecture #23: Arrow pushing:

Halogenation of alkene:

Hydrohalogenation of an alkene:

Markovnikov’s Rule:

Let’s think about these concepts for a bit... What similarities are there between the mechanisms of the halogenation and hydrohalogenation of alkenes? What are some of the differences? How can we use these differences and similarities to help us understand the mechanisms?

Problems:

Fall 2006, Exam #3, Problem 13

13. The following molecules ( A - E ) are proposed products for the reaction of 4- t -butyl-1- cyclohexene and Br (^) 2. Choose the one correct product that will be stable at room temperature.

• Br (^2)

Br

Br

Br

Br

Br

Br

A B

C D E

Br

Br

Br

Br

Fall 2006, Exam #3, Free Response 1

1. To demonstrate that you understand the hydrohalogenation of an alkene, fill in the appropriate boxes and then create an energy diagram that describes this reaction. Make sure to label the energy levels of the alkene starting material, all intermediates, and all products.

Chemistry 104 A/D Discussion Section Worksheet Discussion Section #

• HCl

minor intermediate major intermediate

minor product major product

Spring 2007, Exam #3, Problem 11

11. Which of the following molecules would contain at least one stereocenter after reaction with HBr?

A B C D E