10. Addition Reactions

The following product was obtained from the ozonolysis of an alkene followed by treatment with dimethyl sulfide. What is the structure of the alkene?

a.

Give structures of the alkenes that would give the following products upon ozonolysis–reduction.

(c)

What are the products of the following reactions? Indicate whether each reaction is an oxidation or a reduction.

a.

What products are formed when the following compounds react with ozone and then with dimethyl sulfide?

b.

Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene.

(a)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. (viii) 1. O₃ 2. CH₃SCH₃

(f)

What products are formed when the following compounds react with ozone and then with dimethyl sulfide?

e.

f.

Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.

a.

Predict the product of the following aldehyde/ketone syntheses.

(a)

Professor Patrick Dussault (University of Nebraska at Lincoln) has developed an alternative to the standard two-step ozonolysis procedure requiring reduction of the ozonide in a second step. He uses 2 to 3 equivalents of pyridine, a mildly basic organic solvent, in a one-step process (Organic Letters, 2012, 14, 2242). Show the products you expect from the following examples.

(a)

(b)

For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.

b.

The following products were obtained from the oxidative cleavage of a diene. What is the structure of the diene?

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (viii) 1. O₃ 2. CH₃SCH₃

(d)

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