Date of Award
Union College Only
Bachelor of Science
This project proposes a means for determining whether certain photochemical solvolysis reactions proceed by an SN1 or SN2 type mechanism. The method uses optically active substrates to determine whether the displacement reaction occurs with racemization or retention of configuration. This paper deals with the synthesis of optically active benzyl-α-d alcohol from which various appropriate substrates required for the study can be prepared. Benzaldehyde---d is first prepared by the Stephens reduction of benzonitrile using stannous chloride and deuterium chloride. The optically active alcohol is then prepared by the reduction of thebenzaldehyde-d with optically active isobornyloxymagnesium bromide.
Anes, John Crest, "Synthesis of benzyl-beta-d alcohol for use in studies of photolytic solvolysis reactions" (1969). Honors Theses. 1790.