When an aqueous solution of (R)-2-butanol is treated with a catalytic amount of H2SO4, slow racemization of the alcohol occurs. Explain the result by showing all the steps in the mechanism for this process, including the observation that only a catalytic amount of acid is needed.

When an aqueous solution of (R)-2-butanol is treated with a catalytic amount of H2SO4, slow racemization of the alcohol occurs. Explain the result by showing all the steps in the mechanism for this process, including the observation that only a catalytic amount of acid is needed.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter17: Alcohols And Phenols

Section17.SE: Something Extra

Problem 71AP: A problem often encountered in the oxidation of primary alcohols to acids is that esters are...

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Concept explainers

Diol

In chemistry there are so many chemical compounds that have a hydroxyl group but a chemical compound having two hydroxyl groups (-OH) is termed as a diol. It also implies the presence of two alcohols whereas polyols contain two or more than two hydroxyl groups (-OH). Glycol or 1,2-diol is an aliphatic diol that has two alcohol groups on adjacent carbon atoms. In industries, the most commonly used diol is ethylene glycol.

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When an aqueous solution of (R)-2-butanol is treated with a catalytic amount of H2SO4, slow
racemization of the alcohol occurs. Explain the result by showing all the steps in the mechanism for this
process, including the observation that only a catalytic amount of acid is needed.

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