Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Question
Chapter 23.1, Problem 1P
Interpretation Introduction
Interpretation:
The structural formulas for the given compounds are to be drawn.
Concept Introduction:
>The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of the organic compound is correctly interpreted from the name.
>The number in the name of the organic compounds defines the position for attachment of the
From the word root, suffix, and the numbers in the name of the organic compound, the structural formula can be determined easily.
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PROBLEM 23.26 Draw the mechanism
for the formation of phenol from
bromobenzene and sodium hydroxide
shown in the first reaction. Suppose,
instead, that the deuterium-labeled
bromobenzene shown in the second
reaction were used. What percentage
of the product would you expect to
contain the deuterium atom? Explain.
Br
d
1. NaOH, A
2. H₂O, HCI
OH
6
Br
D
1. NaOH, A
2. H₂O, HCI
22.1 Which of the compounds shown below has the fewest a-
hydrogens?
(a)
H
여
(b)
(c)
(d)
MeO
22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone
is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an
acetoacetic ester synthesis (Section 19.6).
5
3
6
CH₂O
CI
acetoacetic
ester
synthesis
HC
7
MeO
MeO
1
8
2-Methoxynaphthalene
Nabumetone
(a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at
carbon 5 or 7.
(b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum-
etone is completed.
Chapter 23 Solutions
Organic Chemistry - Standalone book
Ch. 23.1 - Prob. 1PCh. 23.3 - Problem 23.2 One of the hydroxybenzoic acids is...Ch. 23.4 - Prob. 3PCh. 23.5 - Prob. 4PCh. 23.6 - Problem 23.5 The compound shown was required for...Ch. 23.8 - Prob. 6PCh. 23.8 - Prob. 7PCh. 23.9 - Prob. 8PCh. 23.9 - Prob. 9PCh. 23.10 - Prob. 10P
Ch. 23.12 - Prob. 11PCh. 23 - The IUPAC rules permit the use of common names for...Ch. 23 - Prob. 13PCh. 23 - Prob. 14PCh. 23 - Prob. 15PCh. 23 - Prob. 16PCh. 23 - Prob. 17PCh. 23 - Prob. 18PCh. 23 - Prob. 19PCh. 23 - Prob. 20PCh. 23 - Prob. 21PCh. 23 - Prob. 22PCh. 23 - Prob. 23PCh. 23 - Prob. 24PCh. 23 - Prob. 25PCh. 23 - Prob. 26PCh. 23 - Choose the reaction in each of the following pairs...Ch. 23 - Pentafluorophenol is readily prepared by heating...Ch. 23 - Prob. 29PCh. 23 - Treatment of p-hydroxybenzoic acid with aqueous...Ch. 23 - Prob. 31PCh. 23 - Prob. 32PCh. 23 - Treatment of 2,4,6-tri-tert-butylphenol with...Ch. 23 - Prob. 34PCh. 23 - Prob. 35PCh. 23 - Prob. 36DSPCh. 23 - Prob. 37DSPCh. 23 - Prob. 38DSPCh. 23 - Prob. 39DSP
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