1) Do the six problems in the Alkane

module of ORGO [Organic Reactions Go

Online] for practice. Work out the problem

BEFORE looking at the answer.

[http://classes.yale.edu/chem220a]

2) The radical chain reaction between ethane and I₂

to form ethyl iodide does not occur yet the

corresponding reaction with Br₂ is successful.

Explain and illustrate with the use of energy

diagrams and the heats of reaction for each

propagation step and for the overall reaction.

3) Why doesn't the radical chain reaction in #2 that forms ethyl bromide proceed as shown below? Illustrate and explain.

4) Draw the structures of the monochlorination

products of 2,2-dimethylbutane? What

percentage of each is formed by radical chain

chlorination of the alkane?

5) Why is the benzylic CH bond dissociation

energy in toluene (1) much lower that the value

for ethane. See pg. 142.

6) Provide 3D representations of the following species and describe in a word their respective geometries: allyl radical, tert-butyl cation, trimethylamine.