
Pearson eText Organic Chemistry -- Instant Access (Pearson+)
8th Edition
ISBN: 9780135213711
Author: Paula Bruice
Publisher: PEARSON+
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Textbook Question
Chapter 9, Problem 126P
Predict the product for the following reaction and write a mechanism to explain how it is formed.
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Draw structures of the following compounds and identify their role:
mCPBA
(MCPBA)
DMS
Py
9-BBN
LAH
Sia₂BH
TsCI
PCC
t-BuOK
LDA
MeLi
n-BuLi
DMSO
DMF
Sodium Borohydride
Lithium DiisopropylAmide
2
Using Luther's rule, calculate the reference potential of the Hg2+/Hg redox electrode.
DATA: Electrode potentials E° = 0,854 V y E 0,788 V
Hg2+/Hg
2+
Hg2/Hg
1) NaNH2 (excess)
1) NaNH2
CI CI
2) H₂O
2) Mel
1) 03
2) (CH3)2S
Na
NH3 (liquid)
1
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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- CI 1) n-BuLi 2) 1) 03 HH T&Cl 2) H₂O 2arrow_forwardHelp with a!arrow_forwardFor the following compound: HO -H Draw a mechanism for the tautomerization process under BASIC conditions: Mechanism A: H-O: H-OH H-O HH H-OO Mechanism B: H-Q Mechanism C: Θ OH H-O: Mechanism D: H-O H- H-OO C H-OO H- H- H-OO HH OH -H - HON H :OH H-Harrow_forward
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- For the following compound: HO H Draw a mechanism for the tautomerization process under BASIC conditions: Mechanism A: + H-O: H-OH₂ H Mechanism B: H-Ö: HO-H H-OO -H H HH H H HH H-O: H-OO H-OO -H H e -H : OH Θ Mechanism C: Θ A : OH H-O: H H H-O-H 0. Mechanism D: e.. : OH :0 H H-O-H H-O: H-OO :O H -H H H сём H 0 :0 + H Θ H H H-arrow_forwardFor the following compound: H OH Draw a mechanism for the tautomerization process under ACIDIC conditions: Mechanism A: Θ :OH O O-H HO 0: Mechanism B: :O-H e.. Θ :OH Mechanism C: H HO-H :0: Θ 0: H H e.. : OH 0: "Θ HH O. :OH :OH O-H O-H Mechanism D: :OH H-OH₂ :OH HO-H 0: © O-H H HH 0: HHarrow_forwardHelp w c!arrow_forward
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