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Predict the products of E1 elimination of the following compounds. Label the major products

Short Answer

Expert verified

(a)

(b)

(c)

Step by step solution

01

Explanation of part (a)

E1 elimination also known as unimolecular elimination, involves two steps—ionization and deprotonation. During ionization, carbocation intermediate is formed; and in deprotonation, a proton is lost by a carbocation. This happens in presence of base, which leads to formation of pi-bond in the molecule. In part (a), the given reactant undergoes E1 mechanism and forms Zaitsev product as major product. The carbocation formed in this E1 reaction is tertiary and will not rearrange.

Products obtained from E1 mechanism

02

Explanation of part (b)

E1 elimination also known as unimolecular elimination, involves two steps—ionization and deprotonation. During ionization, carbocation intermediate is formed; and, in deprotonation, a proton is lost by a carbocation. This happens in presence of base, which leads to formation of pi-bond in the molecule.

In part (b), the given reactant undergoes E1 elimination, and the carbocation produced in this reaction is secondary, and can either eliminate to give first two alkenes, or can rearrange by hydride shift to tertiary carbocation which produces last two products. Last two products are trisubstituted, but first product will certainly be the least.

Formation of products from E1 elimination of (1-bromoethyl)cyclohexane

03

Explanation of part (c)

The given reactant undergoes E1 elimination and the carbocation produced is secondary, and can either eliminate to give first alkene or can rearrange by methyl shift to give tertiary carbocation, which would produce last two products. The middle product is major as it is tetrasubstituted, versus disubstituted for last structure, and monosubstituted for first structure.

Formation of products from E1 elimination of given reactant

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Most popular questions from this chapter

When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsev product predominates.

  1. Draw the reaction, showing the major and minor products.
  2. When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results. For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl group cis. Use your models to draw a Newmanprojection of the transition state to show why this stereospecificity is observed.
  3. Use a Newman projection of the transition state to predict the major product of elimination of (2S,3R)-2-bromo-3-phenylbutane.
  4. Predict the major product from elimination of (2S,3S)-2-bromo-3-phenylbutane. This prediction can be made without drawing any structures, by considering the results in part (b).

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

For each reaction, decide whether substitution or elimination (or both) is possible, and predict the product you expect. Label the major products.

(a) 1 - bromo - 1 - methylcyclohexane + NaOH in acetone

(b) 1 - bromo - 1 - methylcyclohexane + triethylamine (Et3N:)

(c) chlorocyclohexane + NaOCH3 in CH3OH

(d) chlorocyclohexane + NaOC(CH3) in (CH3)3COH

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.

Determine the number of elements of unsaturation in the molecular formula C3H4. Give all three possible structures having this formula. Remember that

a double bond = one element of unsaturation

a ring = one element of unsaturation

a triple bond = two elements of unsaturation

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