10. Addition Reactions

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

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

b. cyclohexene + peroxyacetic acid in water

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)

Show how you would accomplish the following conversions.

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

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?

(d)

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)

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

(b)

When using a terminal alkene under the conditions shown here, explain why it is unnecessary to show the relative stereochemical outcome in the product.

Draw the structure of and name the enantiomeric diols that result from the cis-dihydroxylation of the alkene shown.

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(d)

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

e. trans-pent-2-ene + OsO₄/H₂O₂

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.

(b)

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

(c)

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

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

(d)