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Chapter 7: Q 28P (page 369)

Predict the elimination products of the following reactions and label the major products.

  1. Cis-1-bromo-2-methylcyclohexane +in
  2. Trans-1-bromo-2-methylcyclohexane +in

Short Answer

Expert verified

a.

Major Minor

b.

Major

Step by step solution

01

Explanation of part (a)

For E2 elimination to occur, the hydrogen and leaving group, bromine must have trans-diaxial orientation. The cis-isomer has methyl in equatorial position, the NaOCH3 can remove a hydrogen from either C-2 or C-6, giving a mixture of alkenes where the most highly substituted isomer is the major product (Zaitsev product).

Major Minor

02

Explanation of part (b)

Trans-isomer has methyl in the axial position at carbon-2, so no elimination can occur at C-2. The only possible orientation for elimination reaction to occur is toward C-6. Thus, only one alkene is possible which is not more substituted.

Major

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Most popular questions from this chapter

Finish Solved Problem 7-3 by showing how the rearranged carbocations give the four products shown in the problem. Be careful when using curved arrows to show deprotonation and/or nucleophilic attack by the solvent. The curved arrows always show movement of electrons, not movement of protons or other species.

Give the substitution and elimination products you would expect from the following reactions.

  1. 3-bromo-3-ethylpentane heated in methanol
  2. 1-iodo-1-phenylcyclopentane heated in ethanol
  3. 1-bromo-2-methylcyclohexane + silver nitrate in water (forces ionization)

Question: Draw five more compounds of formulaC4H6NOCl.

Show what happens in step-2 of the example if the solvent acts as a nucleophile (forming a bond to carbon) rather than as a base (removing a proton).

(a) Design an alkyl halide that will give only 2,4-diphenylpent-2-ene upon treatment with potassium tert-butoxide (a bulky base that promotes E2 elimination).

(b) What stereochemistry is required in your alkyl halide so that only the following stereoisomer of the product is formed?
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