Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 8, Problem 9E

(a)

Interpretation Introduction

Interpretation: The curved arrow to show electron movement in the first carbocation rearrangement should be drawn.

Concept introduction: Carbocation is a general term employed for a postively charged carbon irrespective of valency of carbon. In carbocation, carbon is bonded to 3 atoms or groups and has only sextet of electrons so it behaves as an electron-deficient species. It is sp2 hybridized with a vacant p orbital and has a planar geometry.

The order of relative stability of various possible carbocation species is as follows:

  Organic Chemistry: A Guided Inquiry, Chapter 8, Problem 9E , additional homework tip  1

Some special carbocation may attain stability via ring explosion. This also occurs since five-membered rings are more stable than strained three or four-membered ring.

(b)

Interpretation Introduction

Interpretation: The curved arrow to show electron movement in the second carbocation rearrangement should be drawn.

Concept introduction: Carbocation is a general term employed for a postively charged carbon irrespective of valency of carbon. In carbocation, carbon is bonded to 3 atoms or groups and has only sextet of electrons so it behaves as an electron-deficient species. It is sp2 hybridized with a vacant p orbital and has a planar geometry.

The order of relative stability of various possible carbocation species is as follows:

  Organic Chemistry: A Guided Inquiry, Chapter 8, Problem 9E , additional homework tip  2

(c)

Interpretation Introduction

Interpretation: The force that drives this rearrangement should be illustrated.

Concept introduction: Carbocation is a general term employed for a postively charged carbon irrespective of valency of carbon. In carbocation, carbon is bonded to 3 atoms or groups and has only sextet of electrons so it behaves as an electron-deficient species. It is sp2 hybridized with a vacant p orbital and has a planar geometry.

The order of relative stability of various possible carbocation species is as follows:

  Organic Chemistry: A Guided Inquiry, Chapter 8, Problem 9E , additional homework tip  3

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Draw the products of the reaction shown. Electron flow is indicated with curved arrows.
Draw the products of the reaction shown. Electron flow is indicated with curved arrows.

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Organic Chemistry: A Guided Inquiry

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Organic Chemistry: A Guided Inquiry
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ISBN:9780618974122
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