10. Addition Reactions

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

(i)

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

(h)

Predict the major products of the following reactions, including stereochemistry.

c. cis-pent-2-ene + OsO₄/H₂O₂

d. cis-pent-2-ene + peroxyacetic acid in water

Predict the major products of the following reactions, including stereochemistry.

a. cyclohexene + KMnO₄/H₂O (cold, dilute)

b. cyclohexene + peroxyacetic acid in water

Show how you would make the following compounds from a suitable cyclic alkene.

(b)

Show how you would accomplish the following conversions.

d. trans-hex-3-ene to (d,l)-hexane-3,4-diol

Show how you would accomplish the following conversions.

a. cis-hex-3-ene to meso-hexane-3,4-diol

The two butenedioic acids are called fumaric acid (trans) and maleic acid (cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.

Show how you would convert

c. maleic acid to (±)-tartaric acid.

Show how you would make the following compounds from a suitable cyclic alkene.

(a)

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

(j)

Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.

(b)

Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.

(d)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vi) 1. OsO₄ 2. NaHSO₃

(d)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vi) 1. OsO₄ 2. NaHSO₃

(h)