EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
6th Edition
ISBN: 9781305687875
Author: Gilbert
Publisher: CENGAGE LEARNING - CONSIGNMENT
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Chapter 9.3, Problem 6E
Interpretation Introduction
Interpretation: By using curved arrow to symbolize the flow of electron, the mechanism for the propagation steps that converts isopropyl benzene into the corresponding monobromide is to be shown and two possible termination steps for the process are to be described.
Concept introduction: Free radicals are uncharged molecules having an unpaired valence electron.These are typically highly reactive and short-lived molecules.
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Give the substitution and elimination products for the following reactions, showing the configuration of each product. It develops all the steps of the reaction mechanisms.
(a) In an acid-catalyzed hydration, one of the following 10 carbon alkynes is expected to produce a single
hydration product? Select the correct alkyne and draw the structure of the hydration product that is formed from
this alkyne.
(I) 2-decyne; (II) 3-decyne; (III) 4-decyne; (IV) 5-decyne; (V) none of these will give a single hydration
product.
(b) The reaction shown below gives Compound X as the major product. The mass spectrum of X is shown.
Br2, H20
Compound X
100 -
MS-IW-5644
80
60
40 -
20 -
20
40
60
80
100
120
140
160
180
200
220
m/z
Considering the reactions of alkynes and the MS data, de duce which of following structures corresponds to X:
Br
Br
HO,
IV
V
I
II
II
Support your answer with a reaction mechanism for fomation of X and identification of relevant peaks in the
mass spectrum.
12
Relative Intensity
How is the mechanism for oxymercuration/demercuration reactions of alkenes understood?
How are the (Markovnikov) products predicted and what reagents would you need to use to incorporate this reaction into a multistep synthesis strategy.
Finally, what makes this a potentially more useful way to synthesize alcohols from alkenes than simple acid hydration?
Chapter 9 Solutions
EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
Ch. 9.2 - Prob. 1ECh. 9.2 - Prob. 2ECh. 9.2 - Prob. 3ECh. 9.2 - Prob. 4ECh. 9.2 - Prob. 5ECh. 9.2 - Prob. 6ECh. 9.2 - Prob. 7ECh. 9.2 - Prob. 8ECh. 9.2 - Prob. 9ECh. 9.2 - Prob. 10E
Ch. 9.2 - Prob. 11ECh. 9.2 - Prob. 12ECh. 9.2 - Prob. 13ECh. 9.2 - Prob. 14ECh. 9.2 - Prob. 15ECh. 9.2 - Prob. 16ECh. 9.2 - Prob. 17ECh. 9.2 - Prob. 18ECh. 9.2 - Prob. 19ECh. 9.2 - Prob. 20ECh. 9.2 - Prob. 21ECh. 9.2 - Prob. 22ECh. 9.2 - Prob. 23ECh. 9.2 - Prob. 24ECh. 9.3 - Prob. 1ECh. 9.3 - Prob. 2ECh. 9.3 - Prob. 3ECh. 9.3 - Prob. 4ECh. 9.3 - Prob. 5ECh. 9.3 - Prob. 6ECh. 9.3 - Prob. 7ECh. 9.3 - Prob. 8ECh. 9.3 - Prob. 9ECh. 9.3 - Prob. 10ECh. 9.3 - Prob. 11ECh. 9.3 - Prob. 12ECh. 9.3 - Prob. 13ECh. 9.3 - Prob. 14E
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