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Chapter 8: Q. 8-8-71E (page 262)

Hydroxylation of cis-2-butene with OsO4yields a different product than hydroxylation of trans-2-butene. Draw the structure, show the stereochemistry of each product, and explain the difference between them.

Short Answer

Expert verified

Hydroxylation of an alkene with osmium tetroxide happens with syn stereochemistry. Cis reactant leads to the formation of cis product.The reaction occurs by forming a cyclic osmate intermediate in a single step reaction with an alkene, which on oxidation leads to 1,2 diol.

Oxidation of osmate does not affect the stereochemistry of the carbon-oxygen bond.

Step by step solution

01

Hydroxylation of cis-2-butene with OsO4

Hydroxylation of an alkene with osmium tetroxide happens with syn stereochemistry. Cis reactant leads to the formation of cis product.The reaction occurs by forming a cyclic osmate intermediate in a single step reaction with an alkene, which on oxidation leads to 1,2 diol.

Oxidation of osmate does not affect the stereochemistry of the carbon-oxygen bond.

02

Hydroxylation of Trans-2-butene with OsO4

Hydroxylation of an alkene with osmium tetroxide happens with syn stereochemistry. Cis reactant leads to the formation of cis product. The reaction occurs with the formation of a cyclic osmate intermediate in a single step reaction with an alkene, which on oxidation leads to the formation of 1,2 diol.

Oxidation of osmate does not affect the stereochemistry of the carbon-oxygen bond.

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Most popular questions from this chapter

Question: One problem with elimination reactions is that mixtures of products are often formed. For example, treatment of 2-bromo-2-methylbutane with KOH in ethanol yields a mixture of two alkene products. What are their likely structures?

Compound A, C11H16O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a palladium catalyst. On treatment of A with dilute sulfuric acid, dehydration occurred and an optically inactive alkene B,C11H14, was the major product. Alkene B, on ozonolysis, gave two products. One product was identified as propanal,CH3CH2CHO. Compound C, the other product, was shown to be a ketone,C8H8O. How many degrees of unsaturation does A have? Write the reactions, and identify A, B, and C.

Question:Show the structures of alkenes that give the following products on oxidative cleavage with KMnO4 in acidic solution:

c.

When a single alkene monomer, such as ethylene, is polymerized, the product is a homopolymer. If a mixture of two alkene monomers is polymerized, however, a copolymer often results. The following structure represents a segment of a copolymer called Saran. What two monomers were copolymerized to make Saran?

Iodine azide,, adds to alkenes by an electrophilic mechanism similar to that of bromine. If a monosubstituted alkene such as 1-butene is used, only one product results:

c)

In light of the result observed when,adds to 1-butene, what is

the polarity of thebond? Propose a mechanism for the reaction

using curved arrows to show the electron flow in each step.
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