Because deuterium behaves like hydrogen in chemical reactions yet is detected differently, chemists use the incorporation of deuterium to better understand the subtleties of reaction mechanisms. Deuterium is incorporated by replacing H₂ with D₂ in the hydrogenation reaction. Identify the product expected when the alkenes in Assessment 9.34 react with D₂ and Pd/C. [Don't worry about showing all diastereomers.]

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(m)

Give the expected major product for each reaction, including stereochemistry where applicable.

(c)

(d)

Give the expected major product for each reaction, including stereochemistry where applicable.

(a) but-1-ene + H₂/Pt

(b) cis-but-2-ene + H₂/Ni

What product results when the following molecules are treated with H₂ Pd/C? Be sure to indicate the relative stereochemical outcome. Draw both enantiomers of any racemic mixtures. [It is difficult to control the stoichiometry of gases so there is enough H₂ to reduce all alkenes.]

(b)

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)