(a) Give a curved-arrow mechanism for the reaction shown in Fig. P11.70. Be sure your mechanism indicates...

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(a) Give a curved-arrow mechanism for the reaction shown in Fig. P11.70. Be sure your mechanism indicates the role of the weak acid ammonium chloride.

(b) Why does the reaction of an aziridine require this weak acid?

(c) The pKa of ammonium ion is 9.25; the conjugate-acid pKa of an aziridine is about 7; and the pKa of HN3 is 4.2. A student has suggested that dilute (0.01 M)HCl should be an even better catalyst. Critique this suggestion.CNH + Nat N3 + HO sodium azide (see Table 9.1, p. 385) an aziridine Figure P11.70 NHCH, 50 C NH "N3 + NaOH

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Organic Chemistry

ISBN: 9781936221349

6th Edition

Authors: Marc Loudon, Jim Parise

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