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)

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

(l)

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

(f)

Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?

(c)

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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Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(f)

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

e. trans-pent-2-ene + OsO₄/H₂O₂

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

d. a mixture of osmic acid and hydrogen peroxide

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

b. fumaric acid to meso-tartaric acid.