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Predict all the alkenes that would be formed by dehydrohalogenation of the following halides with sodium ethoxide in ethanol and identify the major alkene:

  • (i) - 1-Bromo-1-methylcyclohexane
  • (ii) - 2-Chloro-2-methyl butane
  • (iii) - 2,2,3-Trimethyl-3-bromopentane

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11 Months agoGrade
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ApprovedApproved Tutor Answer11 Months ago

Dehydrohalogenation is a reaction where a hydrogen halide is removed from an alkyl halide, typically resulting in the formation of alkenes. When using sodium ethoxide in ethanol, the reaction favors the formation of alkenes through an elimination mechanism. Below are the predicted alkenes for each halide provided.

1. 1-Bromo-1-methylcyclohexane

This compound can undergo elimination to form:

  • 1-Methylcyclohexene
  • 3-Methylcyclohexene

Major Alkene: 1-Methylcyclohexene is the major product due to less steric hindrance.

2. 2-Chloro-2-methylbutane

For this halide, the possible alkenes formed are:

  • 2-Methylbutene
  • 2,3-Dimethylbutene

Major Alkene: 2-Methylbutene is favored as it is more stable due to hyperconjugation.

3. 2,2,3-Trimethyl-3-bromopentane

This compound can yield the following alkenes:

  • 2,3-Dimethyl-2-pentene
  • 2,3-Dimethyl-3-pentene

Major Alkene: 2,3-Dimethyl-2-pentene is the major product because it is more substituted and thus more stable.

In summary, the major alkenes formed from the dehydrohalogenation of the given halides are 1-Methylcyclohexene, 2-Methylbutene, and 2,3-Dimethyl-2-pentene, respectively.