BackProfessor 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.
(c)
(d)
Predict the major products of the following reactions.
(c)
(d) 1-ethylcycloheptene + ozone, then (CH3)2S
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.
What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
d. O3, −78 °C, followed by (CH3)2S
What aspect of the structure of the alkene does ozonolysis not tell you?
What reagents are needed to carry out the following syntheses?
In contact with a platinum catalyst, an unknown alkene reacts with three equivalents of hydrogen gas to give 1-isopropyl-4-methylcyclohexane. When the unknown alkene is ozonized and reduced, the products are the following:
Deduce the structure of the unknown alkene.