1. Mechanisms and synthesis will be important parts of Exams 2, 3, and the final (and Chem228). Provide mechanisms for the following showing all intermediates, formal charges, and using arrows to show electron flow. a. HO DH NaH H. H D" "D Br THE b/ Br a mixture of -OTs is a tosylate, an aryl sulfonate leaving group NaBr structural OTs -Br isomers are formed Br C. он HBr

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 57AP: All attempts to isolate primary and secondary nitroso compounds result solely in the formation of...
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1. Mechanisms and synthesis will be important parts of Exams 2, 3, and the final (and Chem228). Provide
mechanisms for the following showing all intermediates, formal charges, and using arrows to show electron
flow.
а. но.
DH
NaH
H.
D
"D
Br
THE
b/
Br-
a mixture of
-OTs is a tosylate, an aryl
sulfonate leaving group
NaBr
structural
OTs
Br
isomers
are formed
Br
C.
OH
HBr
.CI
HO
-OH
H CH3
H20
H CH3
H OTf
Br
е.
NaBr
-CH3 CF3CO2H
H
`CH3
cat. H2SO4
f.
H3C X
H3C
ОН
Transcribed Image Text:1. Mechanisms and synthesis will be important parts of Exams 2, 3, and the final (and Chem228). Provide mechanisms for the following showing all intermediates, formal charges, and using arrows to show electron flow. а. но. DH NaH H. D "D Br THE b/ Br- a mixture of -OTs is a tosylate, an aryl sulfonate leaving group NaBr structural OTs Br isomers are formed Br C. OH HBr .CI HO -OH H CH3 H20 H CH3 H OTf Br е. NaBr -CH3 CF3CO2H H `CH3 cat. H2SO4 f. H3C X H3C ОН
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