Workshop 9

Alkenes

1. Write the structures of all the isomeric alkyl bromides having the molecular formula C5H11Br

1.

Which one undergoes E1 elimination at the fastest rate?

2. Which one is incapable of reacting by the E2 mechanism?

3. Which ones can yield only a single alkene on E2 elimination?

4. For which isomer does E2 elimination gives two geometrical isomers?

5. Which one yields the most complex mixture of alkenes on E2 elimination?

What are the products of the following reactions under E2 conditions?

A) (4R, 5S) 4-Bromo-4,5-dimethyloctane:

B) (4R, 5R) 4-Bromo-4,5-dimethyloctane:

2. Given the following reaction:

HBr
OH

H2SO4
CH3

heat

a. Predict the product(s) of the reactions

b. Write the mechanism of the reaction(s)
c. Explain every step in the mechanism of the reaction, molecularity, energy of activation
etc.
d. Is the mechanism that you proposed a concerted or stepwise reaction?
e. If you get more than one product, what conclusion can you reach from the mechanism
of the reaction

3. Show how to carry out the following synthetic transformations using any necessary organic
and inorganic reagents. More than one step may be required.

mixture of compounds predicted

major predicted product