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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

Question: Draw five more compounds of formulaC4H6NOCl.

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

Show that the (S,S) enantiomer of this (R,R) diastereomer of 1-bromo-1,2-diphenylpropane also undergoes E2 elimination to give the cis diastereomer of the product. (We do not expect these achiral reagents to distinguish between enantiomers.)

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).

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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