
Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 17.9, Problem 17.6P
Interpretation Introduction
Interpretation: It should be accounted for the observation that the given
Concept introduction:
Carboxylic acids contain a carbonyl attached to a hydroxyl group as shown below,
If
Decarboxylation of
The mechanism of thermal decarboxylation involves two processes,
- (i) Redistribution of electrons in a cyclic transition state.
- (ii) Cyclic transition state possesses keto-enol tautomerism.
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Record the amounts measured and
calculate the percent yield for Part 2
in the table below.
Dicyclopentadiene
measured in volume
Cyclopentadiene
measured in grams
0
Measured
Calculated
Mol
Yield
Mass (g) or Volume (mL)
Mass (g) or Volume (ml)
0.6
2.955
Part 2 Measurements and Results
Record the amounts measured and calculate the percent yield for Part 2 in the table below.
0.588
0.0044
2.868
0.0434
N/A
Table view List view
Measured
Calculated
Mol
$ Yield
Melting Point (C)
Mass (g) or Volume (ml)
Mass (g) or Volume (ml.)
Cyclopentadiene
0.1
0.08
0.001189
measured in volume
Maleic Anhydride
0.196
N/A
cis-norbornene-5,6-endo-
dicarboxylic anhydride
0.041
0.0002467
N/A
N/A
N/A
0.002
N/A
N/A
128
Draw the condensed structural formula and line-angle formula for each:
2,3-dimethylheptane
3-bromo-2-pentanol
3-isopropyl-2-hexene
4-chlorobutanoic acid
Record the IUPAC names for each of the structures shown below.
a)
b)
c)
OH
d)
OH
e)
Chapter 17 Solutions
Organic Chemistry, Loose-leaf Version
Ch. 17.2 - Prob. 17.1PCh. 17.4 - Which is the stronger acid in each pair?Ch. 17.4 - Prob. 17.3PCh. 17.7 - Prob. 17.4PCh. 17.8 - Prob. 17.5PCh. 17.8 - Prob. AQCh. 17.8 - Prob. BQCh. 17.8 - Prob. CQCh. 17.8 - Permethrin and Bifenthrin Pyrethrin is a natural...Ch. 17.9 - Prob. 17.6P
Ch. 17 - Write the IUPAC name of each compound, showing...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10PCh. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - On a cyclohexane ring, an axial carboxyl group has...Ch. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Complete each reaction.Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Show the reagents and experimental conditions...Ch. 17 - Prob. 17.23PCh. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - In each set, assign the acid its appropriate pKa.Ch. 17 - Low-molecular-weight dicarboxylic acids normally...Ch. 17 - Complete the following acid-base reactions. (a)...Ch. 17 - Prob. 17.29PCh. 17 - Prob. 17.30PCh. 17 - Excess ascorbic acid is excreted in the urine, the...Ch. 17 - Give the expected organic product when...Ch. 17 - Show how to convert trans-3-phenyl-2-propenoic...Ch. 17 - Show how to convert 3-oxobutanoic acid...Ch. 17 - Prob. 17.35PCh. 17 - Prob. 17.36PCh. 17 - Prob. 17.37PCh. 17 - When 4-hydroxybutanoic acid is treated with an...Ch. 17 - Fischer esterification cannot be used to prepare...Ch. 17 - Draw the product formed on thermal decarboxylation...Ch. 17 - Prob. 17.41PCh. 17 - Show how cyclohexanecarboxylic acid could be...Ch. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Write the products of the following sequences of...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Prob. 17.51PCh. 17 - Complete the following Fischer esterification...Ch. 17 - Prob. 17.53P
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