Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 15.8, Problem 6P
Interpretation Introduction

Interpretation:

The reasonable structures for the two products obtained in the reaction of (E)-3-penten-2-ol with the Simmons-Smith reagent are to be suggested.

Concept Introduction:

Methylene transfer from iodomethylzinc iodide to alkene is called the Simmon-Smith reaction. In the overall reaction, an alkene is converted to cyclopropanes.

This reaction is highly stereospecific and the addition of the methylene unit to the double bond is syn.

Substituents that were trans in alkenes remain trans in the cyclopropane.

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Suggest a reasonable series of reagents and reactions conditions to prepare cis-2-methylcyclohexly acetate (A) from trans-2-methylcyclohexanol.
3. Outline a synthetic scheme for the preparation of the compounds A from the suggested starting material by the suggested method. Make sure to clearly indicate all reagents needed to perform each step of the synthetic scheme. (a) OH O=S=O Br A (b) H₂N. (c) HO3S. Br Br A A 1 Br
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Organic Chemistry - Standalone book

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