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 24.22P
Interpretation Introduction
Interpretation:
Concept Introduction:
In catalytic allylic alkylation, a nucleophile, enolate of a doubly activated
Stereochemistry at the alkylation carbon is retained.
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Students have asked these similar questions
b) Optical isomers can often be formed during these reactions. For products A-H
indicate how many different optical isomers you expect to form for each
from these reactions (you do not have to indicate whether they are diastereomers/enantiomers).
c) In the preparation of substance D by ozonolysis, the second step is necessary treatment of the reaction
mixture with zinc in acetic acid. If we forgot this step, we would get substance V instead of substance D, which
would probably explode when isolated. What is the structure of substance V?
*24
X
1: ozone
V
e) What products do you expect to form if they react with alkene X: I - HBr in diethyl ether; II - Brl in methanol; III -
PhSCI in diethyl ether; IV - Selectfluor in methanol.
P
M
EtOH
NA
EtONa
PhSNa
EtOH E
H+
O
TsCl
Pyridín
F-
T2, Pd/C
G4
mCPBA
H₂SO4
10 %, H₂O
1: BH3
H◄
2: H₂O₂
ill
X
Br₂
cyclohexane
HCI
A
> В
B
HBr
warmth,
benzoylperoxid
1: ozone
2: Zn, ACOH
Mg
THF
с
D
D₂O
K
I + J
NaOH
Draw all the resonance forms of the sigma complex for nitration of bromobenzene at the ortho, meta, and para positions. Point out why the intermediate for meta substitution is less stable than the other two.
11) In electrophilic aromatic substitution reactions the nitro group is:
A) a m-director since it destabilizes the meta sigma complex more than the ortho, para.
B) a m-director since it destabilizes the meta sigma complex less than the ortho, para.
C) an o,p-director since it stabilizes the ortho, para sigma complex more than the meta.
D) an o,p-director since it stabilizes the ortho, para sigma complex less than the meta.
E) none of the above.
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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