In 1960, a group of chemists led by Prof. John D. Roberts at Caltech reported that when
Chapter 18, Problem 18.83(choose chapter or problem)
In 1960, a group of chemists led by Prof. John D. Roberts at Caltech reported that when chlorobenzene containing a 14C isotopic label at carbon-1 is treated with the very strong base potassium amide, a substitution product, aniline, is formed in which the isotopic label is equally distributed between carbon-1 and carbon-2 (Fig. P18.83, p. 943). This result was interpreted as evidence for a very interesting unstable intermediate called benzyne. Propose a mechanism for this substitution that accounts for the isotopic labeling result. (Hint: Think about a b-elimination reaction.)
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