10. Addition Reactions

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

(a)

(b)

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

Predict the major products of the following reactions.

(a) (E)-3-methyloct-3-ene + ozone, then (CH₃)₂S

When compound Z is treated with ozone, followed by dimethyl sulfide and washing with water, the products are formic acid, 3-oxobutanoic acid, and hexanal.

Propose a structure for compound Z. What uncertainty is there in the structure you have proposed?

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

(a)

Formation of the molozonide can be expected to proceed stereospecifically. Why is this the case? Show the two different molozonides you would expect to get from ozonolysis of (E)- and (Z)-3,4-dimethylhept-3-ene.

In Solved Assessment 9.30(b), we came up with an alkene that under the conditions of ozonolysis would produce acetophenone and acetaldehyde. There is one other alkene that should produce the same compounds under these conditions. Which is it?

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: (viii) 1. O₃ 2. CH₃SCH₃

(d)

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

(h)

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

(k)

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)

Propose a synthesis of the carbonyl(s) using the (i) ozonolysis pathways.

(a)

Propose a synthesis of the carbonyl(s) using the (i) ozonolysis pathways.

(b)

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

(d)