CHEM 125A: FRESHMAN ORGANIC CHEMISTRY II - Lecture 27 - Professor J. Michael McBride
Triphenylmethyl and an Introduction to Carbonyl Chemistry
Painstaking studies of his "hexaphenylethane" and its reactivity
convinced Gomberg that he had prepared the first trivalent carbon
compound, triphenylmethyl radical, the discovery of which marked the
emergence of fundamental organic chemistry in America. Isotopic labeling
could decide whether protonated cyclopropane plays a role in
Friedel-Crafts alkylation. C-13 NMR spectra of aldehydes and ketones
show how characteristic chemical shifts are established empirically. The
carbonyl group is thermodynamically stable but kinetically reactive.
Its acid- and base-catalyzed reactions often involve loss of α-proton to
form an enol or enolate intermediate. Carboxylic acids display four
fundamentally different reaction patterns. Acid-catalyzed hydrolysis of
acetals illustrates a multistep reaction mechanism involving the
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