Date of Award
2008
Document Type
Honors Thesis (Open Access)
Department
Colby College. Chemistry Dept.
Advisor(s)
Dasan M. Thamattoor
Second Advisor
Jeffrey L. Katz
Third Advisor
Phil Shevlin
Abstract
This thesis is the first report of reactions of atomic carbon with acid chlorides. Carbon is known to react with phosgene to afford dichlorocarbene. We report a similar reaction with carbon and acid chlorides, generating alkylchlorocarbenes. We examine both the nature of the carbene products generated through deoxygenation and the general reactivity of carbon with the acid chlorides. We report two ways in which carbon reacts with acid chlorides. First, as expected from prior work with phosgene, carbon deoxygenates the carbonyl group yielding alkylchlorcarbenes, which rearrange as expected. Second, carbon abstracts the chlorine, and generates the acyl radical, which, in the case of pivaloyl chloride and isobutyryl chloride decarbonylates and a free radical chain reaction mechanism generates the alkyl halide. The reaction of isobutyryl chloride and carbon demonstrates that both the deoxygenation and chlorine abstraction mechanisms compete, as there is a 2:1 ratio of the two processes, respectively.
Keywords
Carbon, Chlorides, Acids, Fullerenes, Reaction
Recommended Citation
Herrick, Daniel B., "Reactions of Atomic Carbon with Acid Chlorides" (2008). Honors Theses. Paper 240.https://digitalcommons.colby.edu/honorstheses/240
Copyright
Colby College theses are protected by copyright. They may be viewed or downloaded from this site for the purposes of research and scholarship. Reproduction or distribution for commercial purposes is prohibited without written permission of the author.