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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

Propose mechanisms to account for the observed products in the following reactions. In some cases, more products are formed, but you only need to account for the ones shown here.

Propose mechanisms and draw reaction-energy diagrams for the following reactions. Pay particular attention to the structures of any transition states and intermediates. Compare the reaction-energy diagrams for the two reactions and explain the differences.

  1. 2-Bromo-2-methylbutane reacts with sodium methoxide in methanol to give 2-methylbut-2-ene (among other products).
  2. 2-Bromo-2-methylbutane reacts in boiling methanol to give 2-methylbut-2-ene (among other products).

When the following stereoisomer of 2-bromo-1,3-dimethylcyclohexane is treated with sodium methoxide, no E2 reaction is observed. Explain why this compound cannot undergo the E2 reaction in the chair conformation.

Show how you would convert (in one or two steps) 1-phenylpropane to the three products shown below. In each case, explain what unwanted reactions might produce undesirable impurities in the product.

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.
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