ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
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Question
Chapter 11.4, Problem 9P
Interpretation Introduction
Interpretation:
The percentage inversion and the percentage racemization occurred when pure tosylate -2,2-dimethyl-1-phenyl-1-propanol reacted with acetic acid is interpreted.
Concept introduction:
The SN1 reaction occurs through carbocation intermediate. The planar achiral carbocation intermediate gives the racemic product.
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Which of the following reactions describes why AICI3 needs to stay dry in order for it to be used in a Freidel Crafts Acylation?
A) 2 AIC13 + 6H2O → 2 Al(OH)3 (s) + 3 Cl2(g) + 6H2(g)
B) AIC13 + 6H2O → [[Al(H2O)5 (OH)]+ H+ + 3 CI
C) AlCl3 +H2O → HAICI3* + OH¯
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The reaction of 1-
methylcyclopentene with
mercuric trifluoroacetate in
ethanol followed by reduction
with sodium borohydride gives
1-ethoxy-1-
methylcyclopentane.
The -OH peak in the IR shows
up at 1700 cm-1 as a sharp
peak.
(S)-2-bromohexane is the
product of the reaction of
(S)-2-hexanol with PBr3.
The 1H NMR spectrum of 1-
pentanol will show a peak for
the H atom of the -OH group
at 10 ppm delta.
A tosylate is a great protecting
group for an alcohol.
The Williamson ether synthesis
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alkyl halide.
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The bromination of trans-cinnamic acid in acetic acid to give a dibromide product is shown in the image. Upon completion, the
reaction mixture is cooled in an ice bath, the resulting crystals are isolated via filtration, and the crystals are then washed with
cold water.
COOH
Br₂
Acetic acid
trans-cinnamic acid
Br
Br
COOH
2,3-dibromo-
3-phenylpropanoic acid
Select the likely purpose of washing the crystals with cold water.
The cold water is used to remove excess Br₂.
The cold water is used to dissolve the dibromide product.
The cold water is used to precipitate trans-cinnamic acid from the acetic acid solvent.
The cold water is used to remove residual acetic acid, CH, COOH.
Chapter 11 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
Ch. 11.1 - Prob. 1PCh. 11.2 - Prob. 2PCh. 11.2 - Prob. 3PCh. 11.3 - Prob. 4PCh. 11.3 - Prob. 5PCh. 11.3 - Rank the following compounds in order of their...Ch. 11.3 - Organic solvents like benzene, ether, and...Ch. 11.4 - Prob. 8PCh. 11.4 - Prob. 9PCh. 11.4 - Prob. 10P
Ch. 11.5 - Rank the following substances in order of their...Ch. 11.5 - 3-Bromo-1-butene and 1-bromo-2-butene undergo SN1...Ch. 11.5 - Prob. 13PCh. 11.6 - Review the mechanism of geraniol biosynthesis...Ch. 11.7 - Prob. 15PCh. 11.7 - What alkyl halides might the following alkenes...Ch. 11.8 - Prob. 17PCh. 11.8 - Prob. 18PCh. 11.9 - Prob. 19PCh. 11.12 - Prob. 20PCh. 11.SE - Prob. 21VCCh. 11.SE - From what alkyl bromide was the following alkyl...Ch. 11.SE - Prob. 23VCCh. 11.SE - Prob. 24VCCh. 11.SE - Prob. 25MPCh. 11.SE - Prob. 26MPCh. 11.SE - Prob. 27MPCh. 11.SE - Prob. 28MPCh. 11.SE - Prob. 29MPCh. 11.SE - Prob. 30MPCh. 11.SE - Prob. 31MPCh. 11.SE - Prob. 32MPCh. 11.SE - Metabolism of S-adenosylhomocysteine (Section...Ch. 11.SE - Reaction of iodoethane with CN- yields a small...Ch. 11.SE - One step in the urea cycle for ridding the body of...Ch. 11.SE - Prob. 36MPCh. 11.SE - Prob. 37MPCh. 11.SE - Propose a mechanism for the following reaction, an...Ch. 11.SE - Prob. 39APCh. 11.SE - The following Walden cycle has been carried out....Ch. 11.SE - Prob. 41APCh. 11.SE - Which reactant in each of the following pairs is...Ch. 11.SE - Prob. 43APCh. 11.SE - Prob. 44APCh. 11.SE - Prob. 45APCh. 11.SE - Prob. 46APCh. 11.SE - Prob. 47APCh. 11.SE - Prob. 48APCh. 11.SE - Propose structures for compounds that fit the...Ch. 11.SE - What products would you expect from the reaction...Ch. 11.SE - Prob. 51APCh. 11.SE - Prob. 52APCh. 11.SE - Prob. 53APCh. 11.SE - Prob. 54APCh. 11.SE - Prob. 55APCh. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Prob. 58APCh. 11.SE - Prob. 59APCh. 11.SE - Ethers can often be prepared by SN2 reaction of...Ch. 11.SE - Show the stereochemistry of the epoxide (see...Ch. 11.SE - Prob. 62APCh. 11.SE - In addition to not undergoing substitution...Ch. 11.SE - The tosylate of (2R, 3S)-3-phenyl-2-butanol...Ch. 11.SE - Prob. 65APCh. 11.SE - Prob. 66APCh. 11.SE - Prob. 67APCh. 11.SE - Prob. 68APCh. 11.SE - Prob. 69APCh. 11.SE - (S)-2-Butanol slowly racemizes on standing in...Ch. 11.SE - Reaction of HBr with (R)-3-methyl-3-hexanol leads...Ch. 11.SE - Treatment of 1-bromo-2-deuterio-2-phenylethane...Ch. 11.SE - Prob. 73APCh. 11.SE - Prob. 74APCh. 11.SE - In light of your answer to Problem 11-74, explain...Ch. 11.SE - Prob. 76APCh. 11.SE - Compound X is optically inactive and has the...Ch. 11.SE - When a primary alcohol is treated with...Ch. 11.SE - Prob. 79APCh. 11.SE - Amines are converted into alkenes by a two-step...Ch. 11.SE - The antipsychotic drug flupentixol is prepared by...
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