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Chapter 7: 16P (page 356)

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).

Short Answer

Expert verified

Methanol acts as nucleophile and attacks the carbocation which neutralizes the positive charge on carbocation. But, oxygen acquires positive charge, and positive charge on electronegative atom is unstable.

Attack of methanol as nucleophile

Step by step solution

01

Attack of methanol as a nucleophile on carbocation:

Methanol acts as nucleophile and attacks the carbocation which neutralizes the positive charge on carbocation. But, oxygen acquires positive charge, and positive charge on electronegative atom is unstable.

Attack of methanol as nucleophile

02

Proton abstraction by methanol and formation of product:

In the second step, to neutralize positive charge on oxygen, methanol acts as base and abstracts proton, which neutralizes the positive charge on oxygen and forms the required product.

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Most popular questions from this chapter

Propose mechanisms for the following reactions. Additional products may be formed, but your mechanism only needs to explain the products shown.

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

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

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)

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).
See all solutions

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