10. Addition Reactions

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

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

(d)

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

(d)

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

(h)

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)