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? **Transcription for Educational Website:****Text:**3. (a) Amides are weak nucleophiles, but the amide drawn below can be deprotonated. One hydrogen is considerably more acidic than the other two. Draw resonance structures (using HO⁻ as the Brønsted-Lowry base) showing electron flow (with arrows) for both conjugate bases. Identify which location is the most acidic in the amide below.**Diagrams:****Diagram 1:**- The diagram shows a chemical structure of an amide.- The structure includes a carbonyl group (C=O) with the oxygen atom having two lone pairs of electrons.- The amide is attached to a nitrogen atom (N) with a lone pair of electrons and three hydrogen atoms.- The carbon atoms are labeled as C_A, C_B, and C_D, each bonded with hydrogen atoms indicated by 'H'.- The structure shows the typical bonding and lone pairs found in an amide group.**Diagram 2:**- A similar structure as Diagram 1, showing the same amide.- Again, the carbonyl group (C=O) is present, with the oxygen atom having two lone pairs.- The nitrogen atom (N) has a lone pair and is bonded to a carbon with three hydrogens.- The carbon atoms are marked as C_A, C_B, and C_D.**Note:** The diagrams emphasize the positioning of lone pairs and hydrogen atoms, crucial for understanding acidity and resonance in amides.

The deprotonation of amides can occur possible from two positions. The Bronsted-Lowry acid-base reactions are represented as: The resonance structure of B and C proton abstraction are given as:The acidic positions of amide are B and C. There are two resonance structures corresponding to proton abstraction from position B. One structure has negative charge on Carbon whereas other has negative charge on Oxygen atom. There are two resonance structures corresponding to proton abstraction from position C. One structure has negative charge on Nitrogen whereas other has negative charge on Oxygen atom. Since, out of Carbon and Nitrogen, negative charge is more stable on more electronegative element, i.e. Nitrogen. Hence, most acidic position of Amide is C (nitrogen) as the conjugate base is more stable. The protonation of amides can occur possible to two positions. The Bronsted-Lowry acid-base reactions are represented as: The resonance structure of C and E (carbonyl oxygen) protonation are given as:The basic positions of amide are Nitrogen and oxygen. There are two resonance structures corresponding to protonation of carbonyl oxygen whereas no resonance stabilization in case of protonation of nitrogen. . Hence, most basic position of Amide is E (oxygen) as the conjugate acid is more stable.