Problem Set 8

Chem 220

Due : Monday, November 3, 1997

Chapter 11

Study the examples in Alkenes on ORGO before doing this PS. Answer the questions

before looking at the answers.

1. A stereoisomer of 1,2-di-n-propyloxirane A reacts with aqueous acid to afford B

(C8H18O2), which is capable of resolution. What are the structures of A and B? Explain

your reasoning. [See Chapter 10]

2. When the stereoisomeric alkenes A and B (C7H14) are oxidized to CO2 and H2O, A is

found to have a greater heat of combustion than B. Upon ozonolysis and zinc reduction,

A and B form two aldehydes, C (C3H6O) and D (C4H8O). Catalytic hydrogenation of A

and B gives E, 2-methylhexane. What are the structures of A - D? Explain your

reasoning.

3. Show how compound A in question 1 can be prepared from an alkene.

4. Compound A undergoes hydroboration to afford B (C7H16O). PCC oxidation of B gives

C, (C7H14O). Ozonolysis and zinc reduction of A yields a ketone D (C3H6O) and E, the

product of PCC oxidation of n-butanol (F). What are the structures of A - E? Explain

your reasoning.

5. Adipic acid, a straight chain, six carbon dicarboxylic acid, is used in the production of

nylon 66. Design a synthesis of adipic acid from cyclohexane.

6. Compound A (C7H12) reacts readily with HCl to form a single compound B (C7H13Cl).

Treatment of B with the hindered base potassium t-butoxide affords A in addition to C

(C7H12). Ozonolysis and dimethyl sulfide reduction of C gives D (CH2O) and E

(C6H10O). E can be prepared from cyclohexene by the following sequence of reactions:

hydroboration, alkaline peroxide oxidation, chromic acid oxidation. What are the

structures of A - E? Explain your reasoning.

7. Provide two methods for the conversion of 1-decene to 1-bromodecane.

8. Compound A is reduced to n-octane by catalytic hydrogenation. Treatment of A with

OsO4 or KMnO4 gives a meso-diol B (C8H18O2). What are the structures of A and B?

Explain your reasoning.

9. Compound A (C6H12) reacts with mercuric acetate in water to form B, C6H14O. PCC

oxidation of B gives C, which is identical to the single product formed by ozonolysis and

dimethyl sulfide reduction of a stereoisomer of 5,6-dimethyl-5-decene (D). D reacts with

OsO4 to afford a racemic diol E. What are the structures of A - E? Explain your

reasoning.