Question

Omeprazole is a racemate of the molecule below and is marketed under the name Prilosec. It is used in the treatment of Gastrointestinal Reflux Disease (GERD). Identify which nitrogen atom in omeprazole is least basic, and justify your choice. o N 5 N (a) Provide an electron pushing mechanism for this reaction: NaOET (b) In the reaction above, what side product could form if Name was used instead of NaOEt? Draw it out

Answer 1

O 3 1 Nitrogen 1 s2 are basic in nature as these nitrogens are of byridine type their lone pair of election are in spa orbital and as the Lone bair are not part of the aromatic sextet (ore) Since the basicity and nucleophilicity of the nitrogen atom are based on the ato avallability of lone pair of Nitrogen atom Im the nitrogen atom given number 3 is of pyrollic type in this nitrogen atom the lone pair of electron are not as Free as in the byridine type nitrogen given ho. IS 2 Im N-3 the Nitrogen lone pair are bort of the aromatic ring system (bre) So- Nitrogen- 3 is least basic. Naoet Naoet H Oet & Na PS st la + И Erol -Product this reaction is known as claisen Condensation reaction to give ß keto ester from estes molecule Ib Moome was used instead of NaOE & the most probabl of the reaction will by be- by product + Ndome -me + Naost Bybroduct This reaction is known as Transesterification.