An abbreviated mechanistic description for DCC-mediated amide bond formation is

Question

An abbreviated mechanistic description for DCC-mediated amide bond formation is illustrated as Path A. An alternative pathway for this process has been proposed as well, illustrated in Path B. In this alternative pathway, a second molecule of acid 1 out-competes the amine 4 for the pivotal activated acyl derivative 3, leading to a transient symmetrical anhydride 7 (with discharge of 6). In Path B, anhydride 7 then is the active electrophile that reacts with amine 4 to give the observed amide product 5 with regeneration of one molecule of acid 1. Assuming that only Path A were operational, what amide product(s) would you anticipate if the reaction were run with 1 equiv. of the racemic amine 9, and a limiting amount (0.1 equiv.) of the chiral diimide 10? Select one: Chiral amide 1 la only. Chiral amide 11 b only. An equal mix of 11a and 11b(= racemic mix). An unequal mix of 11a and 11b.

Explanation / Answer

c) An equal mixture of 11a) and 11b) racemic mixture.

product 11a) show R configuration , 11b) show S configuration.it is 50% inversion and 50% retension of configuration.

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