ORGANIC CHEMISTRY W/OWL
9th Edition
ISBN: 9781305717527
Author: McMurry
Publisher: CENGAGE C
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Question
Chapter 20.SE, Problem 47AP
Interpretation Introduction
a) LiAlH4, then H3O+
Interpretation:
The product produced when p-methylbenzoic acid is treated with LiAlH4 and then with H3O+ is to be predicted.
Concept introduction:
To predict:
The product produced when p-methylbenzoic acid is treated with LiAlH4 and then with H3O+.
Interpretation Introduction
b) N-Bromosuccinimide in CCl4
Interpretation:
The product produced when p-methylbenzoic acid is treated with N-bromosuccinimide in CCl4 is to be predicted.
Concept introduction:
N-bromosuccinimide in CCl4 is used for introducing a Br in the benzyl carbon.
To predict:
The product produced when p-methylbenzoic acid is treated with N-bromosuccinimide in CCl4.
Interpretation Introduction
c) CH3MgBr in ether, then H3O+
Interpretation:
The product produced when p-methylbenzoic acid is treated with CH3MgBr and then with H3O+ is to be predicted.
Concept introduction:
Grignard reagents will react with the carboxyl hydrogen to yield
To predict:
The product produced when p-methylbenzoic acid is treated with CH3MgBr and then with H3O+.
Interpretation Introduction
d) KMnO4, H3O+
Interpretation:
The product produced when p-methylbenzoic acid is treated with KMnO4 in the presence of H3O+ is to be predicted.
Concept introduction:
When treated with KMnO4 in the presence of H3O+, the side chain in
To predict:
The product produced when p-methylbenzoic acid is treated with KMnO4 in the presence of H3O+.
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3. Arrange the different acids in Exercise B # 2 from the strongest (1) to the weakest acid
(10).
1.
2.
(strongest)
3.
4.
5.
6.
7.
8.
9.
10
10.
(weakest)
Name
Section
Score
Date
EXERCISE B
pH, pOH, pка, AND PKD CALCULATIONS
1. Complete the following table.
Solution
[H+]
[OH-]
PH
РОН
Nature of Solution
A
2 x 10-8 M
B
1 x 10-7 M
C
D
12.3
6.8
2. The following table contains the names, formulas, ka or pka for some common acids. Fill
in the blanks in the table. (17 Points)
Acid Name
Formula
Dissociation reaction
Ka
pka
Phosphoric acid
H₂PO₁
H3PO4
H++ H₂PO
7.08 x 10-3
Dihydrogen
H₂PO
H₂PO
H+ HPO
6.31 x 10-6
phosphate
Hydrogen
HPO₁
12.4
phosphate
Carbonic acid
H2CO3
Hydrogen
HCO
6.35
10.3
carbonate or
bicarbonate
Acetic acid
CH,COOH
4.76
Lactic acid
CH₂CHOH-
COOH
1.38 x 10
Ammonium
NH
5.63 x 10-10
Phenol
CH₂OH
1 x 10-10
Protonated form
CH3NH3*
3.16 x 10-11
of methylamine
Indicate whether it is true that Co(III) complexes are very stable.
Chapter 20 Solutions
ORGANIC CHEMISTRY W/OWL
Ch. 20.1 - Give IUPAC names for the following compounds:Ch. 20.1 - Draw structures corresponding to the following...Ch. 20.2 - Prob. 3PCh. 20.2 - The Ka for dichloroacetic acid is 3.32 Ă— 10-2....Ch. 20.3 - Calculate the percentages of dissociated and...Ch. 20.4 - Which would you expect to be a stronger acid, the...Ch. 20.4 - Dicarboxylic acids have two dissociation...Ch. 20.4 - The pKa of p-cyclopropylbenzoic acid is 4.45. Is...Ch. 20.4 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.6 - Prob. 11PCh. 20.6 - How might you carry out the following...Ch. 20.7 - Prob. 13PCh. 20.7 - Prob. 14PCh. 20.8 - Cyclopentanecarboxylic acid and...Ch. 20.8 - Prob. 16PCh. 20.SE - Prob. 17VCCh. 20.SE - Prob. 18VCCh. 20.SE - The following carboxylic acid can’t be prepared...Ch. 20.SE - Electrostatic potential maps of anisole and...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Prob. 23MPCh. 20.SE - Predict the product(s) and provide the complete...Ch. 20.SE - Acid-catalyzed hydrolysis of a nitrile to give a...Ch. 20.SE - Prob. 26MPCh. 20.SE - Naturally occurring compounds called cyanogenic...Ch. 20.SE - 2-Bromo-6, 6-dimethylcyclohexanone gives 2,...Ch. 20.SE - Naturally occurring compounds called terpenoids,...Ch. 20.SE - In the Ritter reaction, an alkene reacts with a...Ch. 20.SE - Give IUPAC names for the following compounds:Ch. 20.SE - Prob. 32APCh. 20.SE - Prob. 33APCh. 20.SE - Prob. 34APCh. 20.SE - Prob. 35APCh. 20.SE - Prob. 36APCh. 20.SE - Prob. 37APCh. 20.SE - Prob. 38APCh. 20.SE - Calculate the Ka's for the following acids: (a)...Ch. 20.SE - Thioglycolic acid, HSCH2CO2H, a substance used in...Ch. 20.SE - Prob. 41APCh. 20.SE - Prob. 42APCh. 20.SE - How could you convert butanoic acid into the...Ch. 20.SE - How could you convert each of the following...Ch. 20.SE - How could you convert butanenitrile into the...Ch. 20.SE - How would you prepare the following compounds from...Ch. 20.SE - Prob. 47APCh. 20.SE - Using 13CO2 as your only source of labeled carbon,...Ch. 20.SE - Prob. 49APCh. 20.SE - Which method-Grignard carboxylation or nitrile...Ch. 20.SE - Prob. 51APCh. 20.SE - Prob. 52APCh. 20.SE - Propose a structure for a compound C6H12O2 that...Ch. 20.SE - Prob. 54APCh. 20.SE - How would you use NMR (either 13C or 1H) to...Ch. 20.SE - Prob. 56APCh. 20.SE - A chemist in need of 2,2-dimethylpentanoic acid...Ch. 20.SE - Prob. 58APCh. 20.SE - Prob. 59APCh. 20.SE - Prob. 60APCh. 20.SE - Prob. 61APCh. 20.SE - Prob. 62APCh. 20.SE - Prob. 63APCh. 20.SE - The following pKa values have been measured....Ch. 20.SE - Identify the missing reagents a-f in the following...Ch. 20.SE - Propose a structure for a compound, C4H7N, that...Ch. 20.SE - Prob. 67APCh. 20.SE - The 1H and 13C NMR spectra below belong to a...Ch. 20.SE - Propose structures for carboxylic acids that show...Ch. 20.SE - Carboxylic acids having a second carbonyl group...
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