Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 11, Problem 11.51P
Interpretation Introduction

Interpretation:

The three carbocation rearrangements in the synthesis of cholesterol from squalene as per Equation 11.38 are to be drawn using curved arrow notation.

Concept introduction:

Carbocations are prone to rearrangements. Generally, this rearrangement is driven by the formation of a more stable carbocation. There are three ways in which a carbocation rearrangement can occur – a 1, 2-hydride shift, a 1, 2-methyl shift, or a resonance rearrangement.

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The question is: "Draw the curved arrow mechanism for the reaction between pentan-2-one and (CH3)3O– in t-butanol to form an enolate. Draw all electrons and charges on both resonance structures. Then answer the question about the reaction." I got the initial arrows correct, but am not entirely sure what the carbanion intermediate would look like and then what the curved arrows would be to convert it to its final oxanion form
Complete the curved arrow notation and include the structure of the missing organic intermediate for the following steps of a nucleophilic aromatic substitution via an addition–elimination mechanism.
10) Consider the following alkene hydration reaction. он H2SO, H20 Given that the reaction is endergonic by 10 kcal/mol, complete the following. (a) Draw the intermediate(s) formed in the mechanistic pathway to the major product in the indicated space below. If there are multiple intermediates label them 1, 2, 3, 4, etc. (b) Sketch a reaction-energy profile for this reaction and clearly label staring material, product, intermediate(s), transition state(s), AG" and AG (of the rate determining step) on your plot. Progress of the reaction Draw and Label Intermediate(s) Below: Potential energy

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Organic Chemistry: Principles and Mechanisms (Second Edition)

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