Jerome Arceneaux Dr. Wang’s Organic I

Worksheet 16 Provide the correct word or phrase for the blank.

1. ____________________ is the competing process for to substitution that takes a proton away

and breaks a bond to create a stable molecule or ion.

2. ____________________ states that the major product of a β-elimination is the most stable

alkene; that is, the alkene with the ___________ number of substituents is more stable.

3. In an _____ elimination, a strong base removes a proton to produce a carbocation.

4. In an _____ elimination, a strong base moves a proton while promoting the expulsion of the

leaving group.

Draw the structural formulas for the alkene(s) formed by treatment of each haloalkane or

halocycloalkane with sodium ethoxide in ethanol.

1.

2.

3.

4.

Jerome Arceneaux Dr. Wang’s Organic I

Worksheet 16

5.

6.

Draw the structural formulas of all chloroalkanes that undergo dehydrohalogenation when treated

with potassium hydroxide to give each alkene as the major product.

1.

2.

3.

4.

Jerome Arceneaux Dr. Wang’s Organic I

Worksheet 16

5.

Elimination of HBr from 2-bromonorbornane gives only 2-norbornene and no 1-norbornene. How do

you account for the regioselectivitity of this dehydrohalogenation?