1. Draw skeletal structures of and give the IUPAC names for 6 alkenes having the formula C5H10 (12%).
2. Draw skeletal structures of and give the IUPAC names for 5 cycloalkanes having the formula C5H10 (10%).
3a. Draw Neuman projections of gauche and anti 1,2-dichloroethane, label each compound and indicate which is lower in energy. (10%)
b. List the four main factors which contribute to steric energies in molecular mechanics calculations. Circle those which you feel would contribute most to the above energy differences. (5%)
4. Draw 3 dimensional structures of all conformers of both cis and trans 1,4-dimethylcyclohexane and answer the following questions (24%):
a. Indicate which structures correspond to the cis and the trans
b. Number the structures you have drawn in order of increasing stability (1 is the least stable)
c. Which is more stable cis or trans-1,4-dimethylcyclohexane? Justify your answer.
5. Complete the following equations. Name all organic reactants and products. (24%)
6. Write the mechanism for the formation of both products in the reaction below. (15%)
