10. Addition Reactions

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

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

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

(h)

Which stereoisomer of 3,4-dimethyl-3-hexene forms (3S,4S)-3,4-dimethylhexane and (3R,4R)-3,4-dimethylhexane when it reacts with 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; and (x) D₂, Pd/C.

(l)

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

(m)

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

(d)

Show how you would accomplish the following transformations. You may use any additional reagents you need.

(d)

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.

One of the principal components of lemongrass oil is limonene, C₁₀H₁₆. When limonene is treated with excess hydrogen and a platinum catalyst, the product is an alkane of ­formula C₁₀H₂₀. What can you conclude about the structure of limonene?

Draw the products, including their configurations, obtained from the reaction of 1-ethylcyclohexene with the following reagents:

b. H₂, Pd/C

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

b. Which stereoisomer is formed in greater yield?

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

(l)