STERIC EFFECTS IN ORGANIC CHEMISTRY PART I SOME CHEMISTRY OF DI-T-BUTYLKETENE PART II ALKALINE HYDROLYSIS OF SUBSTITUTED METHYL BENZOATES

STERIC EFFECTS IN ORGANIC CHEMISTRY PART I SOME CHEMISTRY OF DI-T-BUTYLKETENE PART II ALKALINE HYDROLYSIS OF SUBSTITUTED METHYL BENZOATES

1967 | LEEGWATER, Arie, 1940-
This dissertation, titled "Steric Effects in Organic Chemistry: Part I Some Chemistry of Di-t-Butylketene; Part II Alkaline Hydrolysis of Substituted Methyl Benzoates," was completed by Arie Leegwater in 1967 under the supervision of Dr. Melvin S. Heeman at The Ohio State University. The work focuses on two main areas: the chemistry of di-t-butylketene and the alkaline hydrolysis of substituted methyl benzoates. Part I explores the chemistry of di-t-butylketene, a highly reactive molecule with a cumulative system of olefin and carbonyl double bonds. The study includes the preparation of di-t-butylketene and its reactions with various reagents such as formaldehyde, acetaldehyde, and acetone. The research also investigates the addition of reactive reagents to di-t-butylketene and preliminary photochemical investigations. The results show that di-t-butylketene is relatively unreactive compared to other ketenes, requiring extreme conditions for reaction. However, it can undergo nucleophilic addition under certain conditions, such as the Lewis acid-catalyzed addition of formaldehyde to produce α,α-di-t-butyl-β-propiolactone. The study also considers the potential of di-t-butylketene as a precursor to compounds useful in kinetic and equilibrium studies. Part II examines the alkaline hydrolysis of substituted methyl benzoates. The research includes the preparation of various acids and esters, their structures, and the experimental procedures for hydrolysis. The study analyzes the kinetic data of the hydrolysis reactions, revealing the relative rates of hydrolysis for different esters. The results contribute to the understanding of steric effects in organic chemistry, particularly in the context of reaction mechanisms and the influence of substituents on reaction rates. The dissertation provides a comprehensive analysis of the chemistry of di-t-butylketene and the hydrolysis of substituted methyl benzoates, highlighting the importance of steric effects in organic reactions.This dissertation, titled "Steric Effects in Organic Chemistry: Part I Some Chemistry of Di-t-Butylketene; Part II Alkaline Hydrolysis of Substituted Methyl Benzoates," was completed by Arie Leegwater in 1967 under the supervision of Dr. Melvin S. Heeman at The Ohio State University. The work focuses on two main areas: the chemistry of di-t-butylketene and the alkaline hydrolysis of substituted methyl benzoates. Part I explores the chemistry of di-t-butylketene, a highly reactive molecule with a cumulative system of olefin and carbonyl double bonds. The study includes the preparation of di-t-butylketene and its reactions with various reagents such as formaldehyde, acetaldehyde, and acetone. The research also investigates the addition of reactive reagents to di-t-butylketene and preliminary photochemical investigations. The results show that di-t-butylketene is relatively unreactive compared to other ketenes, requiring extreme conditions for reaction. However, it can undergo nucleophilic addition under certain conditions, such as the Lewis acid-catalyzed addition of formaldehyde to produce α,α-di-t-butyl-β-propiolactone. The study also considers the potential of di-t-butylketene as a precursor to compounds useful in kinetic and equilibrium studies. Part II examines the alkaline hydrolysis of substituted methyl benzoates. The research includes the preparation of various acids and esters, their structures, and the experimental procedures for hydrolysis. The study analyzes the kinetic data of the hydrolysis reactions, revealing the relative rates of hydrolysis for different esters. The results contribute to the understanding of steric effects in organic chemistry, particularly in the context of reaction mechanisms and the influence of substituents on reaction rates. The dissertation provides a comprehensive analysis of the chemistry of di-t-butylketene and the hydrolysis of substituted methyl benzoates, highlighting the importance of steric effects in organic reactions.
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