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

(d)

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, 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.

(j)

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

(k)

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

(l)

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

(m)

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

(n)

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

(o)

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

(p)

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

(q)

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.

a. borane in tetrahydrofuran, followed by basic hydrogen peroxide

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.

b. m-chloroperoxybenzoic acid

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.

(c) ozone, then dimethyl sulfide

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

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.

(e) hot, concentrated potassium permanganate

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.

f. peroxyacetic acid in acidic water

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.

(i) hydrogen bromide gas in a solution containing dimethyl peroxide

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.

m. CHBr₃ and 50% aq. NaOH

Give the products expected when the following compounds are ozonized and reduced.

(a)

(b)

Give the products expected when the following compounds are ozonized and reduced.

(c)

(d)

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

(a)

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

(b)

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

(c)

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

(d)

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

(e)

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

(f)

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.

(a)

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.

(c)

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)