Chem. 262 Notes 4

Chem. 262 Notes 4 - 3-methylcyclohexene from that of...

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Experiment 4: Alcohols undergo elimination reactions to yield alkenes. As a result of the loss of water that occurs, this type of elimination reaction is termed a dehydration reaction which is carried out in a highly acidic media. The direction of elimination is governed by Zaitsev’s rule 1. Illustrate the mechanism of dehydration of 2-methylcyclohexanol, showing how both possible products are formed. 2. (a) What is the ratio of 1-methylcyclohexene to 3-methylcyclohexene? (b) Which one is the major product and why? The experimental ratio of 1-methylcyclohexene to 3-methylcyclohexene is 13% to 87%. The major product is 1-methylcyclohexene because of Zaitzev’s Rule. 3. Proton NMR can be used to differentiate between the two isomers in this experiment. Give two major peak differences in the NMR spectra that can be used to distinguish a sample of pure
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Unformatted text preview: 3-methylcyclohexene from that of 1-methylcyclohexene. The two peaks that could differentiate 1-methylcyclohexene and 3-methylcyclohexene would be the methyl group on the carbon ring that the methyl on 1-methylcyclohexene will encounter deshielding from the neighboring pi bond on the ring. This does not happen for 3-methylcyclohexene. The methyl group for 1-methylcyclohexen would be further downfield. Also, the two pi-bonded hydrogens of the ring in 3-methylcyclohexene would be closer together downfield. The pi-bond proton furthest from the methyl group would have a higher chemical shift because it is located further away from the shielding hydrogens of the methyl....
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This note was uploaded on 05/20/2011 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

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