Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 9, Problem 9.55P
Interpretation Introduction
Interpretation: A step wise, detailed mechanism for the given reaction is to be stated.
Concept introduction: Alcohols undergo dehydration reaction in the presence of strong acids like
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AG/F-2° V
3. Before proceeding with this problem you may want to glance at p. 466 of your textbook
where various oxo-phosphorus derivatives and their oxidation states are summarized.
Shown below are Latimer diagrams for phosphorus at pH values at 0 and 14:
-0.93
+0.38
-0.50
-0.51 -0.06
H3PO4 →H4P206 →H3PO3 →→H3PO₂ → P → PH3
Acidic solution
Basic solution
-0.28
-0.50
3--1.12
-1.57
-2.05 -0.89
PO HPO H₂PO₂ →P → PH3
-1.73
a) Under acidic conditions, H3PO4 can be reduced into H3PO3 directly (-0.28V), or via the
formation and reduction of H4P206 (-0.93/+0.38V). Calculate the values of AG's for both
processes; comment.
(3 points)
0.5
PH
P
0.0
-0.5
-1.0-
-1.5-
-2.0
H.PO,
-2.3+
-3 -2
-1
1
2
3
2
H,PO,
b) Frost diagram for phosphorus under acidic
conditions is shown. Identify possible
disproportionation and comproportionation processes;
write out chemical equations describing them. (2 points)
H,PO
4
S
Oxidation stale, N
4. For the following complexes, draw the structures and give a d-electron count of the
metal:
a) Tris(acetylacetonato)iron(III)
b) Hexabromoplatinate(2-)
c) Potassium diamminetetrabromocobaltate(III)
(6 points)
2. Calculate the overall formation constant for [Fe(CN)6]³, given that the overall formation
constant for [Fe(CN)6] 4 is ~1032, and that:
Fe3+ (aq) + e
= Fe²+ (aq)
E° = +0.77 V
[Fe(CN)6]³ (aq) + e¯ = [Fe(CN)6] (aq) E° = +0.36 V
(4 points)
Chapter 9 Solutions
Organic Chemistry-Package(Custom)
Ch. 9 - Draw all constitutional isomers having molecular...Ch. 9 - Prob. 9.2PCh. 9 - Give the IUPAC name for each compound.Ch. 9 - Problem 9.3 Give the structure corresponding to...Ch. 9 - Prob. 9.5PCh. 9 - Name CH33COCH3, a gasoline additive commonly...Ch. 9 - Name each epoxide.
a. (two ways) b. c. (two...Ch. 9 - Problem 9.6 Rank the following compounds in order...Ch. 9 - Which mechanism is favored by the use of crown...Ch. 9 - Draw the organic product of each reaction.
Ch. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Problem 9.13 Draw the structure of each...Ch. 9 - What other alkene is also formed along with Y in...Ch. 9 - Prob. 9.17PCh. 9 - Explain how the reaction of CH32CHCHCl CH3 with...Ch. 9 - Prob. 9.19PCh. 9 - Draw the products of each reaction, indicating the...Ch. 9 - Problem 9.19 What is the major product formed...Ch. 9 - Prob. 9.22PCh. 9 - Prob. 9.23PCh. 9 - Problem 9.22 Draw the organic products formed in...Ch. 9 - Problem 9.23 Draw two steps to convert into each...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Draw the products of each reaction, and include...Ch. 9 - Draw the products formed when (S)-butan-2-ol is...Ch. 9 - Prob. 9.29PCh. 9 - Prob. 9.30PCh. 9 - Explain why the treatment of anisole with HBr...Ch. 9 - Prob. 9.32PCh. 9 - The cis and trans isomers of 2, 3-dimethyloxirane...Ch. 9 - Problem 9.36 Draw the product of each...Ch. 9 - 9.37 Name each compound depicted in the...Ch. 9 - Answer each question using the ball-and-stick...Ch. 9 - Prob. 9.37PCh. 9 - a. Draw the structure of 1, 2, and 3 alcohol with...Ch. 9 - Give IUPAC name for each alcohol. a....Ch. 9 - Name each ether and epoxide. a.b.c.d.Ch. 9 - Prob. 9.41PCh. 9 - Draw the eight constitutional isomers with...Ch. 9 - Rank each group of compounds in order of: a....Ch. 9 - Prob. 9.44PCh. 9 - 9.44 Why is the boiling point of higher than...Ch. 9 - Draw the organic products formed when CH3CH2CH2OH...Ch. 9 - Draw the organic products formed when 1-methyl...Ch. 9 - What alkenes are formed when each alcohol is...Ch. 9 - Prob. 9.49PCh. 9 - Prob. 9.50PCh. 9 - 9.48 Draw the products of each reaction and...Ch. 9 - Prob. 9.52PCh. 9 - 9.52 Draw a stepwise mechanism for the following...Ch. 9 - 9.53 Although alcohol V gives a single alkene W...Ch. 9 - Prob. 9.55PCh. 9 - Prob. 9.56PCh. 9 - Prob. 9.57PCh. 9 - When CH3CH2CH2CH2OH is treated with H2SO4 NaBr,...Ch. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.60PCh. 9 - Draw two different routes to each of the following...Ch. 9 - Prob. 9.62PCh. 9 - Prob. 9.63PCh. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.66PCh. 9 - Draw the products of each reaction. a.c. b.d.Ch. 9 - When each halohydrin is treated with, a product of...Ch. 9 - Prob. 9.69PCh. 9 - Devise a stepwise mechanism for the following...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Prepare each compound from CH3CH2CH2CH2OH. More...Ch. 9 - Prepare each compound from cyclopentanol. More...Ch. 9 - 9.72 Identify the reagents (a–h) needed to carry...Ch. 9 - Prob. 9.75PCh. 9 - 9.74 Treatment of with affords compound A and ....Ch. 9 - Prob. 9.77PCh. 9 - Prob. 9.78PCh. 9 - 9.77 Draw a stepwise, detailed mechanism for the...Ch. 9 - Dehydration of 1, 2, 2-trimethylcyclohexanol with...Ch. 9 - Prob. 9.81PCh. 9 - 9.80 Draw a stepwise mechanism for the following...Ch. 9 -
9.81 Aziridines are heterocycles that contain an...
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