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Chapter 7: Q62P (page 392)

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.

Short Answer

Expert verified

The mechanisms for the desired products are given.

(a)

(b)

Step by step solution

01

Mechanisms for first three products.

At first the product 2 is formed by elimination, E1 reaction. The leaves to form a secondary carbocation. Then the elimination product is forms with the loss of the adjacent proton. In the second step the nucleophilic addition of methoxy group to the double bond produces the first product 1. Then in the last step the nucleophilic addition occurs again but in the reverse direction to produce the third product 3.

02

Mechanisms for part b

At first the second product 1 is formed by SN 1 reaction. Then the bond of cyclobutane is cleaved and removed methoxy group and formed the product 2. Then by the elimination reaction the product 3 is formed.

(b)

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Most popular questions from this chapter

Question: Give systematic (IUPAC) names of the following alkenes.

(a)

(b)

(c)

(d)

(e)

(f)

Write a mechanism that explains the formation of the following product. In your mechanism, explain the cause of the rearrangement, and explain the failure to form the Zaitsev 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.

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)

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).
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