Question

O EtOCOET H N Eto EtOH 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+, 1, in your answer. • Do not draw organic or inorganic by-products. P [+

Answer 1

-O et + H₂N Eto Eto H Mechaniam Step 1 Nucleophilic attack + EtOH Forenom Et Et 01 H Out Intermediate -1 Step 2 Protomation Depuotomation OH Н H Etor 40 Ost Intermediate-2 O Et H Step 3 Intramolecular collapse of tetrahedal Center in Intermediate 00- *ОН H H to out Exo Intermediate-3 Step=4 Deprotonation 004 10 co Neutral product

Intermediate - 3 A 0H I-Z Et O
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