EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393630817
Author: KARTY
Publisher: W.W.NORTON+CO. (CC)
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Chapter 11, Problem 11.30P
Interpretation Introduction

Interpretation:

The complete, detailed mechanism account for the given reaction is to be drawn.

Concept introduction:

The given alkene undergoes an electrophilic addition reaction via carbocation rearrangement. Electrophilic addition of a Bronstead acid across a carbon-carbon double bond is susceptible to carbocation rearrangement. A carbocation rearrangement transforms the less stable carbocation into a more stable carbocation to attend greater stability via 1, 2-hydride shift or 1, 2-methyl shift. The carbocation rearrangement is followed by the coordination step to form a neutral product.

The carbocation stabilized by resonace is more stable.

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Under aqueous basic conditions, nitriles will react to form a neutral organic intermediate 1 that has an N atom in it first, and then they will continue to react to form the final product 2: NC H₂O он- H₂O 1 2 OH Draw the missing intermediate 1 and the final product 2 in the box below. You can draw the two structures in any arrangement you like. Click and drag to start drawing a structure.
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Assign these C-NMR and H-NMR Spectrum

Chapter 11 Solutions

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M

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How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY