Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 12.9, Problem 17P
Interpretation Introduction

Interpretation: The products formed when both cis and trans-but-2-ene are treated with a peroxyacid followed by OH (in H2O) is to be drawn. An explanation corresponding to the fact that these reactions illustrate that anti dihydroxylation is stereospecific is to be stated.

Concept introduction: Addition of two hydroxyl groups on double bond to form 1,2-diol is known as dihydroxylation. In presence of peroxide, anti dihydroxylation takes place. This reaction occurs in two steps, epoxidation followed by ring opening with the OH.

Stereospecific reactions are those in which the stereochemistry of the reactant controls the stereochemistry of the product.

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Draw the products formed when both cis- and trans-but-2-ene are treated with a peroxyacid followed by −OH (in H2O). Explain how these reactions illustrate that anti dihydroxylation is stereospecific.
Draw the products formed when both cis- and trans-but-2-ene are treated with OsO4, followed by hydrolysis with NaHSO3 + H2O. Explain how these reactions illustrate that syn dihydroxylation is stereospecic.
Draw the products formed when both cis- and trans-but-2-ene are treated with OsO4, followed by hydrolysis with NaHSO3 + H2O. Explain how these reactions illustrate that syn dihydroxylation is stereospecific.

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Organic Chemistry (6th Edition)

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