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

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?

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)