10. Addition Reactions

Show how you would accomplish the following conversions.

c. trans-hex-3-ene to meso-hexane-3,4-diol

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(d)

How might you make the catalytic cycle in Figure 9.31 more sustainable while still using NMO as the co-oxidant?

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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.