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How can 1-bromo-2-methylcyclohexane be transformed into 1-methylcyclohexene via an E2 elimination reaction? What are the necessary conditions and reagents needed for this transformation to occur?

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ago by (610 points)
To transform 1-bromo-2-methylcyclohexane into 1-methylcyclohexene via an E2 elimination reaction, you will need a strong, non-bulky base to facilitate the elimination of the bromine atom and the formation of the double bond. The necessary conditions and reagents for this transformation are as follows:1. Reagent: A strong, non-bulky base, such as potassium tert-butoxide  t-BuOK  or sodium ethoxide  NaOEt . These bases will favor the E2 elimination reaction over other possible side reactions.2. Solvent: A polar aprotic solvent, such as dimethyl sulfoxide  DMSO  or tetrahydrofuran  THF , is suitable for this reaction. These solvents can dissolve both the starting material and the base, and they do not interfere with the reaction.3. Temperature: The reaction should be carried out at a moderately elevated temperature, such as 50-80C, to promote the E2 elimination reaction and ensure a good yield of the desired product.4. Reaction time: The reaction should be allowed to proceed for a sufficient amount of time, typically a few hours, to ensure complete conversion of the starting material to the desired product.The overall reaction can be summarized as follows:1-bromo-2-methylcyclohexane + strong base  e.g., t-BuOK or NaOEt   1-methylcyclohexene + bromide ion  e.g., KBr or NaBr Under these conditions, the strong base will deprotonate the -hydrogen  the hydrogen atom on the carbon adjacent to the bromine-bearing carbon  in an anti-periplanar fashion, leading to the formation of a double bond between the - and -carbons and the elimination of the bromine atom. This results in the formation of 1-methylcyclohexene as the major product.
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