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 6E
Interpretation Introduction

Interpretation: The most likely hydride shift that will occur for each of the below carbocations should be depicted with curved arrow and reason behind lowered potential energy for thus newly formed carbocation should be explained.

  Organic Chemistry: A Guided Inquiry, Chapter 8, Problem 6E , additional homework tip  1

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 6E , additional homework tip  2

Whenever possibility to attain lower energy by rearrangement is there then hydride or alkyl shift may occur and results in more stable carbocation. This type of rearrangement is highly favorable in polar solvents.

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함 H Follow the curved arrows and draw the product of this reaction. . You do not have to consider stereochemistry.
a) Draw the ring-flip isomer of the molecule from question (b) Show which of the two is favored in the equilibrium between them, and explain why, showing all possible forms of strain in each of the isomers. (c) What is the stereochemical relationship between the two isomers? (d) Draw another stereoisomer of the molecule and show all the strains it contains.(strains is the most important one in this questuon!!!)
Predict the product(s) OR starting material of the following reactions. Remember hydride shifts are possible if/when a more stable carbocation can exist (depending on reaction mechanism)! Put only the organic molecules in the boxes.

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Organic Chemistry: A Guided Inquiry

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