Br Br2 Br (minor) HNO3, H2SO4 (major) NON2

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter20: Carboxylic Acids And Nitriles
Section20.SE: Something Extra
Problem 27MP: Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen...
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When N.N-dimethylaniline is treated with bromine, no catalyst is required (why not?), and ortho and nara
educts are observed. Yet when N,N-dimethylaniline is treated with a mixture of nitric and sulfuric acid
only the meta product is observed after a neutralizing reaction workup. Explain these results-draw
mechanistic details, including intermediates, to support your explanation.
Br2
Br
+
Br
HNO3, H2SO4
(minor)
(major)
NO2
Transcribed Image Text:When N.N-dimethylaniline is treated with bromine, no catalyst is required (why not?), and ortho and nara educts are observed. Yet when N,N-dimethylaniline is treated with a mixture of nitric and sulfuric acid only the meta product is observed after a neutralizing reaction workup. Explain these results-draw mechanistic details, including intermediates, to support your explanation. Br2 Br + Br HNO3, H2SO4 (minor) (major) NO2
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