Custom eBook for Organic Chemistry
Custom eBook for Organic Chemistry
2nd Edition
ISBN: 9798214171104
Author: Straumanis
Publisher: Cengage Custom
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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.

  Custom eBook for Organic Chemistry, 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:

  Custom eBook for Organic Chemistry, 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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Done 11:14 ⚫ worksheets.beyondlabz.com 5 (a). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 6 5 (b). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 7 6. Are there any differences between the spectra you obtained in Beyond Labz and the predicted spectra? If so, what were the differences? <
2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

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