Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 22.SE, Problem 37AP
Identify all the acidic hydrogens (pKa < 25) in the following molecules:
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Structure
pK,
K.
Name
NH;
CHCH,-O
2.20 (СО,Н)
9.31 (NH,)
6.3 X 10-3
4.9 x 10-10
Phenylalanine
CO,H
7.11 x 10-3
6.34 x 10-8
2.148
* 7.198
Phosphoric acid*
(hydrogen phosphate)
НО — Р— Он
12.375
4.22 X 10-13
OH
(1.5)
6.78
3 x 10-2
1.66 x 10-7
HP-
он
Phosphorous acid
(hydrogen phosphite)
OH
1.12 x 10-3
3.90 x 10-6
2.950
Phthalic acid
(benzene-1,2-dicarboxylic acid)
5.408
cO,H
Piperazine
(perhydro- 1,4-diazine)
5.333
9.731
4.65 x 10-6
1.86 X 10-10
11.125
7.50 x 10-12
Piperidine
1.12 x 10-2
2.29 x 10-11
-co,H
1.952 (СO,Н)
10.640 (NH,)
Prolinc
+H
4.874
1.34 x 10-5
Propanoic acid
CH,CH,CO,H
H,C=CHCO,H
4.258
5.52 x 10-5
Propenoic acid
(аcrylic acid)
10.566
2.72 x 10-11
Propylamine
CH;CH,CH,NII;
5.20
6.3,X 10-6
Pyridine
(azine)
Pyridine-2-carboxylic acid
(picolinic acid)
(1.01) (CO,H)
5.39 (NH)
9.8 x 10-2
4.1 x 10-6
co,H
HO,C
Pyridine-3-carboxylic acid
(nicotinic acid)
2.03 (CO,H)
4.82 (NH)
9.3 x 10-3
1.51 x 10-s
NH+
1.4 (POH) (u = 0.1)
3.44 (OH) (1p. = 0.1)
6.01 (POH) (u = 0.1)
8.45 (NH) (u =…
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
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