10. Addition Reactions

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

(h)

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

(k)

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

(k)

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)

The chiral catalyst (R)-BINAP(COD)RhOTf was used in a hydrogenation reaction as part of the synthesis of fragment C of indinavir. Using the same alkene, predict the product that would be obtained if (S)-BINAP(COD)RhOTf were used instead.

On a per alkene basis, which would have the more negative heat of hydrogenation?

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

(b) H₂ , Ni (partial hydrogenation)

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.

(e)

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.

(l)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br₂ (ii) Cl₂

(l)

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)

a. What stereoisomers are formed in the following reaction? Are they enantiomers or diastereomers?

b. Which stereoisomer is formed in greater yield?

What are the products of the following reactions? Indicate whether each reaction is an oxidation or a reduction.

b.

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

f. 1,2-dideuteriocyclohexene + H₂, Pd/C

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

k. (Z)-3,4-dimethyl-3-hexene + H₂, Pd/C

l. (E)-3,4-dimethyl-3-hexene + H₂, Pd/C