QUESTIONNAIRE PSYKMO2 LONG EXAM 1 SET B
DE LA SALLE UNIVERSITY
DEPARTMENT OF CHEMISTRY
Problem Solving. Clearly draw structures/give the corresponding answer to each item.
1. Draw the structure of the molecule: 1,1,3-trimethylcyclopentene. (3 pts)
2. Draw only ONE structure of the product/s of each chemical reaction. If there is more than one possible product due to the stereochemistry, just choose one. (3 pts each)
Figure 1: alpha-pinene
A. How many degrees of unsaturation are present in the structure of alpha-pinene (Figure 1)? Show your solution.
B. Is alpha-pinene a water-soluble compound? Justify your answer.
C. Hydrohalogenation with HCl
D. Hydration with 1.BH/2.HOOH
E. Halogenation with I
F. Hydrogenation with H/Pd-C
G. Syn-dihydroxylation with 1.OsO4/2.NaHSO3, H2O
H. Oxidative cleavage with 1.O/2.ZnHO
3. Answer the following questions for the molecule 2,5-dimethyl-3-hexyne. (3 pts each)
A. Draw the structure of the molecule.
B. Draw the product from the reduction reaction with Na/NH.
C. Draw the product from the Hydroboration-oxidation reaction with HO/HSO.
D. Draw the product from the oxidative cleavage with 1.O/2.HO.
E. Draw the product of the reaction with Br2 equiv.
F. Draw the product for the reaction with H/Lindlar's catalyst.
4. Draw the complete mechanism from the chosen item below (Choose only ONE. 5 pts)
A. The mechanism for the reaction of 2-butene with HBr.
B. The mechanism for the reaction of 2-butene with Cl.
C. The mechanism for the reaction of 2-butene with HO/HSO.
5. Give the starting material and reagents needed to prepare 2,5-dimethyl-3-hexyne from an alkyne and an alkyl halide. (5 pts)