Preparation and sodium-ammonia reduction of some conjugated alkadienes

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Authors
Brane, Richard Daniel
Subjects
Alkadiene synthesis
Alkadiene reduction
Dehydration
Sodium-ammonia reduction
Birch reduction
Advisors
Cardenas, Carlos G.
Date of Issue
1967-05
Date
May 1967
Publisher
Monterey, California. U.S. Naval Postgraduate School
Language
en_US
Abstract
A series of alkadienes was prepared by the dehydration of unsaturated c7 and c8 alcohols. The dienes were separated by G .P.C. techniques and identified by their NMR and IR spectra. The UV data of the conjugated dienes was also recorded. The dehydration of 4-ethyl-l-hexen-4-ol gave three dienes, 4-ethyl-l, 3-hexadiene, 4-ethyl-l, 4-hexadiene and 3-ethyl-2, 4-hexadiene. The dehydration of 4-methyl-l-hexen-4-ol gave four dienes, 4-methyl-1, 4-hexadiene, 2-ethyl-1, 4-pentadiene, 4-methyl-l, 3-hexadiene and 3-methyl-2, 4-hexadiene. The dehydration of 4-octen-2-ol gave 1, 3-octadiene and 2, 4-octadiene in about equal amounts. The sodium-ammonia reduction products of 2, 5-dimethyl-2, 4-hexadiene, 1, 3-octadiene, and 2, 4-octadiene were determined. The reduction of 2, 5-dimethyl-2, 4-hexadiene gave both the symmetrical and unsymmetrical olefin as reduction products. One reduction of 1, 3-octadiene gave 2-octene. The other reductions of 1, 3-octadiene and 2, 4-octadiene gave mixtures of olefins as their monomeric products.
Type
Thesis
Description
Series/Report No
Department
Department of Material Science and Chemistry
Organization
Naval Postgraduate School
Identifiers
NPS Report Number
Sponsors
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Format
Citation
Distribution Statement
Approved for public release; distribution is unlimited.
Rights
This publication is a work of the U.S. Government as defined in Title 17, United States Code, Section 101. Copyright protection is not available for this work in the United States.
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