As shown in the following equation, when (R)-1-deuterio-1-butanamine is diazotized with nitrous acid in water, the alcohol

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As shown in the following equation, when (R)-1-deuterio-1-butanamine is diazotized with nitrous acid in water, the alcohol product formed has the S configuration (D = 2H).D T H CH3CHCH NH HNO HO (R)-1-deuterio-1-butanamine HO D "H CHCHCH3

(a) Give the stereochemical configuration of the diazonium ion formed as an intermediate in this reaction. Draw its structure.

(b) What mechanism for reaction of the diazonium ion with water is consistent with the stereochemical result in the preceding equation?

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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