ELOČOET H2N EtO 'N. H + ELOH 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. You do not have to consider stereochemistry. In cases where there is more than one answer, just give one. • Do not include counter-ions, e.g., Na", I", in your answer. Do not draw organic or inorganic by-products.

ELOČOET H2N EtO 'N. H + ELOH 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. You do not have to consider stereochemistry. In cases where there is more than one answer, just give one. • Do not include counter-ions, e.g., Na", I", in your answer. Do not draw organic or inorganic by-products.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Section21.SE: Something Extra

Problem 36MP: When 4-dimethylaminopyridine (DMAP) is added in catalytic amounts to acetic anhydride and an...

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