Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 24, Problem 24.30P
Interpretation Introduction
Interpretation:
The coupling reaction and the staring material to form the given product has to be identified.
Concept Introduction:
Stille coupling uses a tin reagent (
Stille coupling gives conjugated dienes or alkenyl aryl system.
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Acyl transfer (nucleophilic substitution at carbonyl) reactions
proceed in two stages via a "tetrahedral intermediate." Draw
the tetrahedral intermediate as it is first formed in the
following reaction.
CH3OH
H3C
CI
•
•
•
•
You do not have to consider stereochemistry.
Include all valence lone pairs in your answer.
Do not include counter-ions, e.g., Na+, I", in your
answer.
In cases where there is more than one answer, just
draw one.
41. Zaitsev’s rule states that:
the alkene with less alkyl substituents is the major product in base-induced elimination reactions
the more highly substituted carbocation is formed as the intermediate rather than the less highly substituted one
the alkene with more alkyl substituents is the major product in base-induced elimination reactions
the less highly substituted carbocation is formed as the intermediate rather than the more highly substituted one
Do hydration reactions like this one have Markovnikov and anti-Markovnikov products? I know that for addition of halides on alkene double bonds, there are Markovnikov products becasue of 1,2-halide/methyl shifts, but there usually aren't shifts in hydration reactions.
Essentially, would the Markovnikov/major product for this reaction have a hydroxy group attached to the tertiary carbocation and the anti-Markovnikov/minor product for this reaction have a hydroxy group attached to the adjacent secondary carbocation?
Chapter 24 Solutions
Organic Chemistry
Ch. 24.3 - Prob. 24.1PCh. 24.3 - Prob. 24.2PCh. 24.4 - Prob. 24.3PCh. 24.5 - Show how the following compound can be prepared...Ch. 24.5 - Prob. 24.5PCh. 24.5 - Prob. 24.6PCh. 24.6 - Prob. 24.7PCh. 24 - Prob. 24.8PCh. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Treatment of cyclohexene with iodobenzene under...Ch. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - The aryl diene undergoes sequential Heck reactions...Ch. 24 - Heck reactions take place with alkynes as well as...Ch. 24 - Prob. 24.16PCh. 24 - The following transformation involves a series of...Ch. 24 - Show the sequence of Heck reactions by which the...Ch. 24 - Prob. 24.19PCh. 24 - Write the steps that are critical in the following...Ch. 24 - Prob. 24.21PCh. 24 - Prob. 24.22PCh. 24 - Prob. 24.23PCh. 24 - Show how the following compound could be prepared...Ch. 24 - It is typically very difficult to do a...Ch. 24 - The compound eutypine is an antibacterial agent...Ch. 24 - Prob. 24.27PCh. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - Prob. 24.30PCh. 24 - Prob. 24.31PCh. 24 - Prob. 24.32PCh. 24 - Prob. 24.33PCh. 24 - The following transformation can be accomplished...Ch. 24 - Prob. 24.35PCh. 24 - Prob. 24.36PCh. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - E. J. Coreys 1964 total synthesis of...Ch. 24 - Prob. 24.40P
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