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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Textbook Question
Chapter 15, Problem 15.20P
Write the products of the following sequences of reactions. Refer to your reaction roadmaps to see how the combined reactions allow you to “navigate” between the different
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Convert 2-pentanol into 2,3-dibromopentane. Draw structures of the starting material (2-pentanol) and final product
(2,3-dibromopentane), and show the two reactions needed for this synthesis. Include the structure of the intermediate
compound, and the reagents and conditions for each reaction. Then explain why 1,2-dibromopentane would not be a
significant product of this synthesis.
Starting with benzene and using any other reagents of your choice, design a synthesis for the following compound:
COOH
NO₂
COOH
The target molecule above can be prepared by treating benzene with some reagent or combination of the reagents listed below. Give
the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than
one correct solution, provide just one answer.
A
Mel, AlCl3
B
KMnO4, NaOH, heat
(followed by
H3O+ workup)
C
HCI, Zn
D
E
F
(CH3)2CHCI, AICI 3
HNO3, H2SO4
Fuming H2SO4
How would you synthesize the following substances from benzaldehyde and reagents from the table? In general, the fewer the steps, the better the synthesis. You should not need
more than four steps.
Use letters from the table to list reagents in the order used (first at the left) with no commas.
Example: cag
Reagents
a
CH2=0
f 1. CH3MgBr / dry ether
2 H3O+
j 1. P(C6H5)3
2. BuLi
b
O
g
Dess-Martin periodinane
KA
Br2
in CH2Cl2
C
(C6H5)3P+-CH2
h
1. NaBH4
1. PBг3
2. H3O+
d
m
NH + acid
i
1. BH3/THF
NaNH2/NH3
2. H2O2 / NaOH
e
CrO3/H3O+
n
Mg/ dry ether
a)
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Chapter 15 Solutions
Organic Chemistry
Ch. 15.1 - Explain how these Grignard reagents would react...Ch. 15.1 - Recalling the reactions of alcohols from Chapter...Ch. 15.2 - Prob. 15.3PCh. 15.2 - Show how to prepare each Gilman reagent in Example...Ch. 15.2 - Predict the product of the following reaction.Ch. 15.2 - Show how the following compound could be prepared...Ch. 15 - Complete these reactions involving lithium...Ch. 15 - Show how to convert 1-bromopentane to each of...Ch. 15 - Prob. 15.9PCh. 15 - Show how to prepare each compound from the given...
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Show how the following compound can be prepared in...Ch. 15 - Prob. 15.15PCh. 15 - Show how spiro[2.2]pentane can be prepared in one...Ch. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - We now continue the introduction of organic...Ch. 15 - Write the products of the following sequences of...Ch. 15 - Using your old and new reaction roadmaps as a...Ch. 15 - Using your old and new reaction roadmaps as a...Ch. 15 - Using your old and new reaction roadmaps as a...Ch. 15 - Using your old and new reaction roadmaps as a...Ch. 15 - Prob. 15.25PCh. 15 - Gilman reagents are versatile reagents for making...
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