Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 19.6, Problem 19.6P
Rank each set of compounds in order of increasing basicity.
- a. NaOH, NH3, CH3NH2, Ph-NH2
- b. aniline, p-methylaniline, p-nitroaniline
- c. aniline, pyrrole, pyridine, piperidine
- d. pyrrole, imidazole, 3-nitropyrrole
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Rank the compounds in each group in order of increasing basicity.
NH2
NH2
NH2
a. NH3
-NH2
-NH2
c.
O,N
CH3
b.
d. C3H;NH, (C6H5)2NH
-NH2
N'
H
H
Rank the compounds in each group in order of increasing acidity.
ÇI
Br
.COOH
„COOH
COOH
а.
COOH
COOH
COOH
CH
CF3
LOH
HO
HO
HO
HO
HO
b.
d.
CH
O,N
Br
O,N
O,N
`NO2
Rank the compounds in each group in order of increasing basicity.
NH2
NH2
NH2
a. NH3
-NH2
-NH2
c.
O,N
CH3
b.
d. CgHgNH2 (C,H5)2NH
-NH2
N.
H
H
C.
Arrange the follwoing in order of decreasing basicity.
OH-, CH3COOH, CH3CH2-, NH2-, NH3, Cl-
Chapter 19 Solutions
Organic Chemistry (9th Edition)
Ch. 19.2A - Prob. 19.1PCh. 19.2B - Prob. 19.2PCh. 19.2B - Give correct names for the following amines:Ch. 19.3 - Prob. 19.4PCh. 19.4 - Prob. 19.5PCh. 19.6 - Rank each set of compounds in order of increasing...Ch. 19.8A - Prob. 19.7PCh. 19.8C - Prob. 19.8PCh. 19.8C - Prob. 19.9PCh. 19.8D - a. Show how fragmentation occurs to give the base...
Ch. 19.10B - Propose a mechanism for nitration of pyridine at...Ch. 19.10B - Prob. 19.12PCh. 19.10C - Prob. 19.13PCh. 19.10C - Prob. 19.14PCh. 19.11 - Propose a mechanism to show the individual...Ch. 19.11 - Prob. 19.16PCh. 19.12 - Give the products expected from the following...Ch. 19.13 - Prob. 19.18PCh. 19.13 - Prob. 19.19PCh. 19.14 - Prob. 19.20PCh. 19.15 - Prob. 19.21PCh. 19.15 - Prob. 19.22PCh. 19.16 - Prob. 19.23PCh. 19.17 - Prob. 19.24PCh. 19.17 - Prob. 19.25PCh. 19.18 - Prob. 19.26PCh. 19.19 - Prob. 19.27PCh. 19.20A - Addition of one equivalent of ammonia to...Ch. 19.20A - Prob. 19.29PCh. 19.20B - Show how you would accomplish the following...Ch. 19.20C - Prob. 19.31PCh. 19 - For each compound, 1. classify the...Ch. 19 - Prob. 19.33SPCh. 19 - Within each structure, rank the indicated...Ch. 19 - In each pair of compounds, select the stronger...Ch. 19 - Which of the following compounds are capable of...Ch. 19 - Complete the following proposed acid-base...Ch. 19 - Predict the products of the following reactions:...Ch. 19 - Prob. 19.39SPCh. 19 - Show how m-toluidine can be converted to the...Ch. 19 - The mass spectrum of tert-butylamine follows shows...Ch. 19 - Prob. 19.42SPCh. 19 - The following drugs are synthesized using the...Ch. 19 - Prob. 19.44SPCh. 19 - Synthesize from benzene. (Hint: All of these...Ch. 19 - Propose mechanisms for the following reactions.Ch. 19 - Prob. 19.47SPCh. 19 - Prob. 19.48SPCh. 19 - Prob. 19.49SPCh. 19 - Show how you can synthesize the following...Ch. 19 - Prob. 19.51SPCh. 19 - The alkaloid coniine has been isolated from...Ch. 19 - A chemist is summoned to an abandoned...Ch. 19 - Pyrrole undergoes electrophilic aromatic...Ch. 19 - Prob. 19.55SPCh. 19 - Prob. 19.56SPCh. 19 - An unknown compound shows a weak molecular ion at...Ch. 19 - A compound of formula C11H16N2 gives the IR,...Ch. 19 - (A true story.) A drug user responded to an ad...Ch. 19 - Prob. 19.60SPCh. 19 - Prob. 19.61SPCh. 19 - Prob. 19.62SPCh. 19 - Prob. 19.63SPCh. 19 - Prob. 19.64SPCh. 19 - Prob. 19.65SP
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