10. Addition Reactions

Which of the following compounds is not a product of the ozonolysis of $1-\mathrm{butene}$?

Which of the following products are formed when $\mathrm{cyclohexene}$ undergoes ozonolysis followed by reductive workup with ${\mathrm{Zn}}_{H}O$?

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.

(i)

Ozonolysis of an unknown alkene A gives the products shown. Predict the product that results from hydrogenation of alkene A. [There are multiple answers, but only show the one with the 6-membered ring.]

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

c.

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

c.

d.

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

c.

Which of the following products is formed by ozonolysis of ${\mathrm{CH}}_2={\mathrm{CH}}_2$ (ethene)?

Which of the following alkenes would yield ${\mathrm{CH}}_3\mathrm{CHO}$ (acetaldehyde) and $\mathrm{CH}{3}_2\mathrm{CO}$ (acetone) as the only products upon ozonolysis?

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

(l)

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.

(e)

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

a.

Draw the product(s) you'd expect when each of these alkenes is treated first with O₃, then with CH₃SCH₃

(c)

What alkenes would give only an aldehyde with four carbons as a product of oxidative cleavage

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

(b)