EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
6th Edition
ISBN: 9781305687875
Author: Gilbert
Publisher: CENGAGE LEARNING - CONSIGNMENT
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Chapter 9.3, Problem 11E
(a)
Interpretation Introduction
Interpretation: Based on Hammond’s postulate the greater selectivity for bromination Vs chlorination of an
Concept Introduction : Hammond’s postulate can be described as the transition state of reaction matches with the reactants or products and with its energy.
(b)
Interpretation Introduction
Interpretation: Based on Hammond postulate, the fact of the relative reactivity of C-H bonds of an alkane for free radical chain halogenation to be 3° > 2°> 1º needs to be explained.
Concept Introduction :
Hammond’s postulate can be described as the transition state of reaction matches with the reactants or products and with its energy.
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7) You want to synthesize 3-methyl-2-pentene from 2-chloro-3-methylpentane. Which reagent
would you use?
a. HCI, heat
b. NH:(aq), 25°C
c. CH:CO2NA, CH:CO2H, heat
d. CH3CH2ONA, CH3CH2OH, heat
e. CН:CH2ОН, heat
3. Write the structure of the alkene X, that forms the compound below, when treated with ozone (O3)
and Zn and Acetic Acid or (CH3)2S workup. X=?
X+ (1) Ozone + (2) Zn, Acetic Acid
CH
CCH
H20, H2SO4
H9SO4
CH3
Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov
regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called
an enol. The enol immediately rearranges to a more stable ketone via tautomerization.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
Hjö:
-CH3
-CH3
H3O*
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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