Chapter 5 Quiz

1. (2 points) Give complete IUPAC names for each of the following:

a)

(E)-4-cyclopentyl-2,3-dimethyl-3-penten-1-ol

b)

(2E,4Z,6E)-4-chloro-2,4,6-octatriene

2. (3 points) Write a complete mechanism for the dehydration reaction shown below. Just show the pathway to the major product. Show all steps and use electron-pushing arrows.

3. (5 points) Write all three conformations of 1-bromo-1-chlorobutane, using Newman diagrams looking down the C1-C2 bond.
Bromide is a much better leaving group than chloride, and the products are (E) and (Z)-1-chloro-1-butene.
Illustrate which conformation(s) give each product in an E2 elimination, and predict the major product.