Record Details
Addition of hydrogen bromide to unsymmetrical olefins
ScholarsArchive at Oregon State University
| Field | Value |
|---|---|
| Title | Addition of hydrogen bromide to unsymmetrical olefins |
| Names |
Rogers, Charles Junior
(creator) Logan, A. V. (advisor) |
| Date Issued | 1957-08-22 (iso8601) |
| Note | Graduation date: 1953 |
| Abstract | In this investigation the addition of hydrogen bromide to 3-methylcyclohexene has been studied in order to see if the theory of hyperconjugation could be extended to include olefins of this type. Since the olefin has an equal number of hydrogens on both carbons carrying the double bond, a mixture of bromides was expected in the addition product. The bromides expected were cis-2- or trans-2-bromomethyl-cyclobexane or a mixture of the isomers and cis-3- or trans-3-bromomethylcyclohexane or a mixture or those isomers. An infrared method of analyzing the addition product was used. To use this method it was necessary to make up known mixtures of the compounds expected in the addition product. In order to prepare some of the isomeric bromides, trans-2- and trans-3-methylcyclohexanol were prepared. Then, because no good methods could be found in the literature for the conversion of isomeric alcohols to isomeric bromides, the alcohols were not used. Instead, the known mixtures for the infrared work were prepared from 2-bromo- and 3-bromo-methylcyclohexanes, both containing unknown amounts of the cis-trans isomers. The 3-methylcyclohexene used in the hydrogen bromide addition was prepared from 3-bromomethylcyclohexene and methylmagnesium iodide. The addition of hydrogen bromide was conducted at 0°C and at room temperature using glacial acetic acid as a solvent. The addition product was obtained in a very low yield and was very difficult to isolate. The product isolated was found to be about 70 per cent 3-bronomethylcyclohexane. Because of the low yield and isolation difficulties, no conclusions could be drawn regarding hyperconjugation. |
| Genre | Thesis/Dissertation |
| Topic | Alkenes |
| Identifier | http://hdl.handle.net/1957/51277 |
