10. Addition Reactions

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)

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

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

a.

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

c.

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

e.

What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?

a.

What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?

c.

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

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

c.

d.

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.

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

b.

One of the constituents of turpentine is α-pinene, formula C₁₀H₆. The following scheme (called a “road map”) gives some reactions of α-pinene. Determine the structure of α-pinene and of the reaction products of A through E.

Problem 8-54 describes a new method to perform ozonolysis reactions that used pyridine (py) to generate the final aldehydes and ketones in a non-aqueous reaction medium. In a subsequent publication (J. Org. Chem., 2013, 78, 42), Professor Dussault (U. of Nebraska at Lincoln) described a “tandem” process in which two reactions are performed sequentially without having to isolate the intermediate aldehyde or ketone. Show the final product from each sequence. (Hint: The isolated products were from the larger part of the structure. Ignore stereochemistry.)

(a)

(b)

Problem 8-54 describes a new method to perform ozonolysis reactions that used pyridine (py) to generate the final aldehydes and ketones in a non-aqueous reaction medium. In a subsequent publication (J. Org. Chem., 2013, 78, 42), Professor Dussault (U. of Nebraska at Lincoln) described a “tandem” process in which two reactions are performed sequentially without having to isolate the intermediate aldehyde or ketone. Show the final product from each sequence. (Hint: The isolated products were from the larger part of the structure. Ignore stereochemistry.)

(c)

(d)