Publication Date

1983

Document Type

Dissertation/Thesis

First Advisor

Miller, F. M. (Fred Mathias), 1905-1992

Degree Name

M.S. (Master of Science)

Legacy Department

Department of Chemistry

LCSH

Alcohols; Mercury compounds; Acetic acid

Abstract

The addition reactions of acetic acid to acetylenic alcohols in the presence of mercury(II) acetate have been studied. In this reaction, acetylenic alcohols, when refluxed in acetic acid and catalytic amount of mercury(II) acetate, gave α-acetoxy ketone. ... Tertiary acetylenic alcohols, such as 2-methyl-3-butyn-2-ol, were found to react more rapidly and more completely than secondary or primary acetylenic alcohols, while saturated tertiary alcohol under the same reaction conditions was found to be less reactive than secondary or primary saturated alcohols. 2-Hydroxy-2-methyl-3- butanone, 2-butyn-l-ol, 3-butyn-l-ol, allyl alcohol, 1- hexyne, 2-methoxy-2-methyl-3-butyne were also treated in the same manner. The reactions of 2-methyl-3-butyn-2-ol were also carried out separately in methanol or nitro- ethanol in presence of mercury(II) acetate and trace of p-toluenesulfonic acid. Comparison of the results obtained suggest the neighboring hydroxyl group participate in the formation of the α-acetoxy ketone by attacking the mercurinium complex to form an epoxide ring. Opening this epoxide ring, either by the attack of acetic acid or by rupture to a carbocation, leads to the acetoxy ketone.

Comments

Bibliography: pages 43-46.

Extent

46 pages

Language

eng

Publisher

Northern Illinois University

Rights Statement

In Copyright

Rights Statement 2

NIU theses are protected by copyright. They may be viewed from Huskie Commons for any purpose, but reproduction or distribution in any format is prohibited without the written permission of the authors.

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