10. Addition Reactions

Using any alkene and any other reagents, how would you prepare the following compounds?

a.

Draw the structure of a compound with molecular C₈H₁₄ that reacts with one equivalent of H₂ over Pd/C to form a meso compound

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D₂, Pd/C.

(h)

Identify the product when each of the following reactions is performed on the triglyceride of linoleic acid (linoleate).

(b) H₂ , Ni (partial hydrogenation)

Provide the product of the following reaction.

Draw the products of the following reactions, including their configurations:

A misguided chemist attempted to synthesize trans-1,2-dimethylcyclohexane via the hydrogenation of 1,2-dimethylcyclohexene. Explain why this is not possible.

Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

i. (Z)-3,4-dimethyl-3-heptene + H₂, Pd/C

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H₂, Pd/C

(k)

What stereoisomers would you expect to obtain from each of the following reactions?

c.

d.

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H₂, Pd/C; and (x) D₂, Pd/C.

(f)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D₂ , Pd/C.

(k)

Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.

i. (Z)-2,3-dichloro-2-butene + H₂, Pd/C

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(e)

What alkene would you start with if you wanted to synthesize

a. pentane?