organic chemistry 60

1. Consider the isomers of C




5




H




10




.

a. Draw and name all the structural isomers of C




5




H




10




.

b. Give an example of a set of geometric isomers of C




5




H




10




(i.e. cis and


trans).

2. Consider the molecule 2-methylhexane.

a. Sketch the line drawing (skeletal structure) below.

b. Draw the most stable Newman projection(s) about the C3-C4 bond.

c. Draw the least stable Newman projection(s) about the C3-C4 bond.

d. How many of the C-C bonds have equally stable staggered conformers?

3. Explain why dioctylether has a higher boiling point than ethanol.

7. Draw and rank the relative stability of the four chair conformations 1-




ethyl-2-propylcyclohexane. Remember two of these conformations will be the cis


isomer and two will be the trans isomer.