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15 February, 21:18

Identify possible products of dehydrohalogenation of cis-1-bromo-2-methylcyclohexane

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  1. 15 February, 21:34
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    cis-1-bromo-2-methylcyclohexane on E2 reaction yield two different cycloalkenes. This is because cis-1-bromo-2-methylcyclohexane contains two different axial beta hydrogen atoms. Therefore, base can abstract both of them forming two different products.

    As shown below, the two axial beta hydrogens are specified as Ha and Hb.

    When base abstracts Ha proton then it produces 3-methylcyclohex-1-ene, which is a minor product.

    And when base abstracts Hb proton the product formed is 1-methylcyclohex-1-ene. This is a major product because it has tri-substituted double bond hence more stable according to Zaitsev rule.
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