Pearson eText Organic Chemistry -- Instant Access (Pearson+)
8th Edition
ISBN: 9780135213711
Author: Paula Bruice
Publisher: PEARSON+
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Question
Chapter 9, Problem 80P
(a)
Interpretation Introduction
Interpretation:
Among the given reactions, the reaction takes place more rapidly has to be identified.
Concept Introduction:
The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.
The configuration of the product is inverted relative to the configuration of the reactant.
Steric effect is the effect due to the groups occupies a certain volume of space.
Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.
(b)
Interpretation Introduction
Interpretation:
Among the given reactions, the reaction takes place more rapidly has to be identified.
Concept Introduction:
The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.
(c)
Interpretation Introduction
Interpretation:
Among the given reactions, the reaction takes place more rapidly has to be identified.
Concept Introduction:
The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism. The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.
The configuration of the product is inverted relative to the configuration of the reactant.
Steric effect is the effect due to the groups occupies a certain volume of space.
Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.
(d)
Interpretation Introduction
Interpretation:
Among the given reactions, the reaction takes place more rapidly has to be identified.
Concept Introduction:
The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism.
The stronger base is always a better nucleophile in an aprotic solvent.
Protic solvent are polar solvent molecules which have hydrogen bonded to oxygen to nitrogen.
The stronger base is always a better nucleophile in an aprotic solvent.
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Draw the anti-Markovnikov product of the hydration of this alkene.
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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
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P
0.0
-0.5
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-2.0
H.PO,
-2.3+
-3 -2
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2
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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
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Oxidation stale, N
Chapter 9 Solutions
Pearson eText Organic Chemistry -- Instant Access (Pearson+)
Ch. 9.1 - Prob. 3PCh. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.1 - Prob. 8PCh. 9.2 - Prob. 9PCh. 9.2 - Prob. 10PCh. 9.2 - Prob. 11PCh. 9.2 - Prob. 12PCh. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 15P
Ch. 9.2 - Prob. 17PCh. 9.3 - Prob. 18PCh. 9.4 - Prob. 19PCh. 9.5 - Draw the configuration(s) of the substitution...Ch. 9.5 - Which of the following reactions take place more...Ch. 9.7 - Prob. 22PCh. 9.7 - Prob. 23PCh. 9.7 - Prob. 24PCh. 9.7 - Prob. 25PCh. 9.8 - Four alkenes are formed from the E1 reaction of...Ch. 9.8 - If 2-fluoropentane could undergo an E1 reaction,...Ch. 9.8 - Prob. 28PCh. 9.8 - Propose a mechanism for the following reaction:Ch. 9.9 - Prob. 30PCh. 9.9 - What percentage of the reaction described in...Ch. 9.10 - Prob. 33PCh. 9.10 - Prob. 35PCh. 9.11 - Why do cis-1-bromo-2-ethylcyclohexane and...Ch. 9.11 - Which isomer reacts more rapidly in an E2...Ch. 9.11 - Prob. 38PCh. 9.12 - Prob. 39PCh. 9.12 - Prob. 40PCh. 9.12 - Prob. 41PCh. 9.12 - Explain why only a substitution product and no...Ch. 9.12 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 9.13 - Prob. 44PCh. 9.13 - Prob. 45PCh. 9.13 - What products will be obtained from the El...Ch. 9.13 - Prob. 47PCh. 9.13 - Prob. 48PCh. 9.13 - Prob. 49PCh. 9.13 - Why is a cumulated diene not formed in the...Ch. 9.13 - What product is obtained when the following...Ch. 9.13 - What products are formed from the following...Ch. 9.14 - Prob. 54PCh. 9.14 - Prob. 55PCh. 9.14 - Prob. 56PCh. 9.14 - Prob. 58PCh. 9.14 - Under which of the following reaction conditions...Ch. 9.15 - A small amount of another organic product is...Ch. 9.15 - What is the best way to prepare the following...Ch. 9.15 - Prob. 62PCh. 9.15 - What products (including stereoisomers, if...Ch. 9.16 - After a proton is removed from the OH group, which...Ch. 9.16 - Prob. 65PCh. 9.17 - Prob. 66PCh. 9 - Prob. 1PCh. 9 - Methoxychlor is an insecticide that was intended...Ch. 9 - Prob. 67PCh. 9 - Prob. 68PCh. 9 - Prob. 69PCh. 9 - Prob. 70PCh. 9 - Prob. 71PCh. 9 - Prob. 72PCh. 9 - Starting with cyclohexene, how can the following...Ch. 9 - Prob. 74PCh. 9 - The pKa of acetic acid in water is 4.76. What...Ch. 9 - Prob. 76PCh. 9 - Prob. 77PCh. 9 - Prob. 78PCh. 9 - Prob. 79PCh. 9 - Prob. 80PCh. 9 - Prob. 81PCh. 9 - Prob. 82PCh. 9 - Draw the major product obtained when each of the...Ch. 9 - Prob. 84PCh. 9 - a. Indicate how each of the following factors...Ch. 9 - Prob. 86PCh. 9 - A chemist wanted to synthesize the...Ch. 9 - Prob. 88PCh. 9 - Prob. 89PCh. 9 - Prob. 90PCh. 9 - Prob. 91PCh. 9 - Starting with an alkyl halide, how could the...Ch. 9 - Indicate which species in each pair gives a higher...Ch. 9 - Prob. 94PCh. 9 - Rank the following from most reactive to least...Ch. 9 - For each of the following alkyl halides, indicate...Ch. 9 - Prob. 97PCh. 9 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 9 - Prob. 100PCh. 9 - When the following compound undergoes solvolysis...Ch. 9 - cis-1-Bromo-4-tert-butylcyclohexane and...Ch. 9 - Draw the substitution and elimination products.Ch. 9 - tert-Butyl chloride undergoes solvolysis in both...Ch. 9 - Prob. 105PCh. 9 - Prob. 106PCh. 9 - In which solventethanol or diethyl etherwould the...Ch. 9 - Prob. 108PCh. 9 - Two bromoethers are obtained from the reaction of...Ch. 9 - Prob. 110PCh. 9 - Prob. 111PCh. 9 - Prob. 112PCh. 9 - Which of the following hexachlorocyclohexanes is...Ch. 9 - Explain why the rate of the reaction of...Ch. 9 - Prob. 115PCh. 9 - Two elimination products are obtained from the...Ch. 9 - Draw the structures or the product of the obtained...Ch. 9 - How could you prepare the following compounds from...Ch. 9 - cis-4-Bromocyclohexanol and...Ch. 9 - Prob. 120PCh. 9 - Propose a mechanism for the following reaction:Ch. 9 - Prob. 122PCh. 9 - Prob. 123PCh. 9 - Prob. 124PCh. 9 - Prob. 125PCh. 9 - Predict the product for the following reaction and...Ch. 9 - Prob. 127PCh. 9 - Prob. 128PCh. 9 - When equivalent amounts of methyl bromide nod...Ch. 9 - Prob. 130PCh. 9 - The reaction of chloromethane with hydroxide ion...
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