The observation that reaction of cis -2-butene with m -chloroperoxybenzoic acid yields an epoxide different from that obtained by reaction of the trans isomer is to be explained. Concept introduction: The formation of epoxides when an alkene is treated with peroxyacids involves the transfer of an oxygen atom of the peroxyacid to the double bond in the alkene with syn stereochemistry through a one step process without intermediates. To explain: The observation that reaction of cis -2-butene with m -chloroperoxybenzoic acid yields an epoxide different from that obtained by reaction of the trans isomer.

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2) There are many forms of cancer, all of which involve abnormal cell growth. The growth and production of cells, called cell proliferation, is known to involve an enzyme called protein farnesyltransferase (PFTase). It is thought that inhibitors pf PFTase may be useful as anticancer drugs. The following molecule showed moderate activity as a potential PFTase inhibitor. Draw all stereoisomers of this compound. HO OH

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Question

Chapter 18.5, Problem 11P

Interpretation Introduction

Interpretation:

The observation that reaction of cis-2-butene with m-chloroperoxybenzoic acid yields an epoxide different from that obtained by reaction of the trans isomer is to be explained.

Concept introduction:

The formation of epoxides when an alkene is treated with peroxyacids involves the transfer of an oxygen atom of the peroxyacid to the double bond in the alkene with syn stereochemistry through a one step process without intermediates.

To explain:

The observation that reaction of cis-2-butene with m-chloroperoxybenzoic acid yields an epoxide different from that obtained by reaction of the trans isomer.

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