#85 Which of the following types of compounds is the MOST basic?
A) Primary alcohols B) Esters C) Secondary amines D) Tertiary thiols
#26 asked, "The most stable hydrogen-bond between amides extends from the.." and the answer was "the carbonyl oxygen to the H on N." I chose B when working on #85, primarily because I remembered reading in the explanation for #26 that the carbonyl oxygen of an amide forms the strongest hydrogen bond because the N of the amide donates electrons through resonance pushing out electrons on the O, making O a better electron donor. Why doesn't the same hold true for #85 in regards to esters? I was also confused by the fact that the explanation for #85 says that esters have no lone pairs to readily donate to a proton.
A) Primary alcohols B) Esters C) Secondary amines D) Tertiary thiols
#26 asked, "The most stable hydrogen-bond between amides extends from the.." and the answer was "the carbonyl oxygen to the H on N." I chose B when working on #85, primarily because I remembered reading in the explanation for #26 that the carbonyl oxygen of an amide forms the strongest hydrogen bond because the N of the amide donates electrons through resonance pushing out electrons on the O, making O a better electron donor. Why doesn't the same hold true for #85 in regards to esters? I was also confused by the fact that the explanation for #85 says that esters have no lone pairs to readily donate to a proton.