The Effects of Electron-Donating and Electron-Withdrawing Groups on the Alkylation Sites of Para-Substituted Phenylacetones

Author

Abraham L. Faburada

Date of Award

8-1978

Degree Name

Master of Arts

Department

Chemistry

First Advisor

Dr. Don C. Iffland

Second Advisor

Dr. Donald C. Berndt

Third Advisor

Dr. Jochanan Stenesh

Access Setting

Masters Thesis-Open Access

Abstract

The dianions of phenylacetone and its para-substituted derivatives were generated using potassium hydride and n-butyl lithium in tetrahydrofuran. Methyl, ethyl, and n-butyl iodides were used to alkylate the dianions. The results of alkulation indicated that C₁ is preferentially attacked by the less active ethyl and n-butyl iodides. The results further show that terminal alkylation is enhanced by electron-donating groups at the para-position of the phenyl ring. The results are rationalized in terms of the difference in electron density at C₁ and at C₃ in the dianion, on the basis of resonance theory. The regio-selectivity of alkylation as a function of the alkylating agent's activity, and the factors which appear to dictate the fate of alkylation between carbon and oxygen in the ambident dianion are discussed.

Recommended Citation

Faburada, Abraham L., "The Effects of Electron-Donating and Electron-Withdrawing Groups on the Alkylation Sites of Para-Substituted Phenylacetones" (1978). Masters Theses. 2100.
https://scholarworks.wmich.edu/masters_theses/2100