Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Question
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
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In the partial mechanism for the formation of cholesterol from squalene (Equation 11-38, p. 593), the steps for
the following transformation were not shown explicitly. As indicated, the transformation involves three carbocation
rearrangement steps. Draw each step and its curved arrow notation explicitly.
H
H
CH3
CH3 CH
CH3
H
CH3
Three carbocation
H
CH3
rearrangements
HO
НО
В
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
Help me
Chapter 11 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 11 - Prob. 11.1PCh. 11 - Prob. 11.2PCh. 11 - Prob. 11.3PCh. 11 - Prob. 11.4PCh. 11 - Prob. 11.5PCh. 11 - Prob. 11.6PCh. 11 - Prob. 11.7PCh. 11 - Prob. 11.8PCh. 11 - Prob. 11.9PCh. 11 - Prob. 11.10P
Ch. 11 - Prob. 11.11PCh. 11 - Prob. 11.12PCh. 11 - Prob. 11.13PCh. 11 - Prob. 11.14PCh. 11 - Prob. 11.15PCh. 11 - Prob. 11.16PCh. 11 - Prob. 11.17PCh. 11 - Prob. 11.18PCh. 11 - Prob. 11.19PCh. 11 - Prob. 11.20PCh. 11 - Prob. 11.21PCh. 11 - Prob. 11.22PCh. 11 - Prob. 11.23PCh. 11 - Prob. 11.24PCh. 11 - Prob. 11.25PCh. 11 - Prob. 11.26PCh. 11 - Prob. 11.27PCh. 11 - Prob. 11.28PCh. 11 - Prob. 11.29PCh. 11 - Prob. 11.30PCh. 11 - Prob. 11.31PCh. 11 - Prob. 11.32PCh. 11 - Prob. 11.33PCh. 11 - Prob. 11.34PCh. 11 - Prob. 11.35PCh. 11 - Prob. 11.36PCh. 11 - Prob. 11.37PCh. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - Prob. 11.40PCh. 11 - Prob. 11.41PCh. 11 - Prob. 11.42PCh. 11 - Prob. 11.43PCh. 11 - Prob. 11.44PCh. 11 - Prob. 11.45PCh. 11 - Prob. 11.46PCh. 11 - Prob. 11.47PCh. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - Prob. 11.50PCh. 11 - Prob. 11.51PCh. 11 - Prob. 11.52PCh. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - Prob. 11.55PCh. 11 - Prob. 11.56PCh. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - Prob. 11.59PCh. 11 - Prob. 11.60PCh. 11 - Prob. 11.61PCh. 11 - Prob. 11.1YTCh. 11 - Prob. 11.2YTCh. 11 - Prob. 11.3YTCh. 11 - Prob. 11.4YTCh. 11 - Prob. 11.5YTCh. 11 - Prob. 11.6YTCh. 11 - Prob. 11.7YTCh. 11 - Prob. 11.8YTCh. 11 - Prob. 11.9YTCh. 11 - Prob. 11.10YTCh. 11 - Prob. 11.11YTCh. 11 - Prob. 11.12YTCh. 11 - Prob. 11.13YTCh. 11 - Prob. 11.14YT
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