Amides are weak nucleophiles but their conjugate bases are string nucleophiles. The amide drawn below can be deprotonated in four possible locations, labeled A-D but two are considerably more acidic than the others. Draw the two different Bronsted Lowery acid/base reactions (using HO- as the BL base) showing the deprotonation at these two locations. Draw all RS with arrows for both conjugate bases but no hybrids. Based on your resonance analysis which location is the most acidic in the molecule? Why is it most acidic? Amides can also be protonated by a strong acid in two different locations. Draw two different conjugate acids for the amide above as well as RS with arrows for each. Based on your resonance analysis which atom is the most basic in an amide?

Amides are weak nucleophiles but their conjugate bases are string nucleophiles. The amide drawn below can be deprotonated in four possible locations, labeled A-D but two are considerably more acidic than the others. Draw the two different Bronsted Lowery acid/base reactions (using HO- as the BL base) showing the deprotonation at these two locations. Draw all RS with arrows for both conjugate bases but no hybrids. Based on your resonance analysis which location is the most acidic in the molecule? Why is it most acidic? Amides can also be protonated by a strong acid in two different locations. Draw two different conjugate acids for the amide above as well as RS with arrows for each. Based on your resonance analysis which atom is the most basic in an amide?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter20: Acidity And Pka Of Phenols

Section: Chapter Questions

Problem 9E

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