PS2

1. Predict the number of mono-chlorinated compounds from the reaction of each C7H16
isomer with chlorine at high temperature.

2. Given 2,3-dimethylpentane, draw the structures of mono-chlorinated compounds formed

upon its reaction with chlorine in the presence of sunlight. Include stereoisomers, if any.

3. Reactivity of halogens is as follows: F2 > Cl2 > Br2 > (I2). Chlorine is reactive and reacts
with all free radical intermediates. Bromine, on the other hand, is selective and reacts
only with the most stable free radical intermediate.

a. Draw the structure/s of mono-brominated compound/s upon the reaction of 3-

ethylpentane with bromine at high temperature. Include stereoisomers, if any.

b. Give the mechanism of the reaction.

4. Among the 12 cyclic compounds of C6H12:

a. Which structures will exhibit geometric isomerism?

b. Which structures are chiral? Label the chiral carbons with *.