of triphenylmethyl radical hexaphenylethane

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter23: Amines
Section: Chapter Questions
Problem 23.67P
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The triphenylmethyl radical is an unusual persistent radical present in
solution in equilibrium with its dimer. For 70 years the dimer was thought
to be hexaphenylethane, but in 1970, NMR data showed it to be A.

a.) Why is the triphenylmethyl radical more stable than most other
radicals?
b.) Use curved arrow notation to show how two triphenylmethyl radicals
dimerize to form A.
c.) Propose a reason for the formation of A rather than hexaphenylethane.
d.) How could 1H and 13C NMR spectroscopy be used to distinguish
between hexaphenylethane and A ?

of
triphenylmethyl radical
hexaphenylethane
Transcribed Image Text:of triphenylmethyl radical hexaphenylethane
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