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Chemistry, 31.01.2020 17:03, jamarstand
Reactions of a primary or secondary amine with diethyl carbonate under controlled conditions gives a carbamic ester. write a detailed mechanism for this reaction (shown above) which proceeds in 4 steps, including proton transfer steps. then draw intermediate 3 in the window provided.
the mechanism is detailed as follows:
step 1: nucleophilic attack to yield zwitterion intermediate 1.
step 2: protonation/deprotonation (i. e. "proton transfer") of zwitterion 1 to yield intermediate 2.
step 3: intramolecular collapse of tetrahedral center in intermediate 2 to yield charged intermediate 3.
step 4: deprotonation of intermediate 3 to yield neutral product.
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