Doctoral Dissertations

Abstract

"In order to investigate the possibility of resonance effects through a non-coplanar substituted acetylene, synthesis of bis-(2,5,8-trimethyl-l-naphthyl)-acetylene was attempted. Condensation of acetylene with 2,5,8-trimethyl-l-tetralone to yield an acetylenic glycol followed by dehydration and dehydrogenation was expected to yield the desired non-coplanar acetylene. Comparison of its ultraviolet spectrum with that of di-l-naphthyl-acetylene would have suggested the true nature of the acetylene pi cloud. The acetylene condensation was unsuccessful, however.

Substituted allenes, which contain one sp hybridized carbon atom, were then successfully synthesized for a similar analysis of potential resonance effects. A series of para-substituted 4-phenyl-2-methylbutadienoic acids were synthesized and their pKa's determined in water solution. The pKa's of the para-methyl, para-chloro and para-hydrogen substituted allenic acids were identical, indicating that resonance effects are not transmitted through the allene function"--Abstract, page iii.

Advisor(s)

Russell, Robert R.

Committee Member(s)

Wulfman, David S., 1934-2013
Hanna, Samir B.
Webb, William H.
Stoffer, James O.

Department(s)

Chemistry

Degree Name

Ph. D. in Chemistry

Publisher

University of Missouri at Rolla

Publication Date

1967

Pagination

vi, 76 pages

Note about bibliography

Includes bibliographical references (pages 71-74).

Rights

© 1967 Robert Andrew Steinkamp, All rights reserved.

Document Type

Dissertation - Open Access

File Type

text

Language

English

Subject Headings

Acetylene compounds
Allene
Cumulenes

Thesis Number

T 1986

Print OCLC #

5981356

Electronic OCLC #

908454838

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