Why are amides less easy to hydrolyze than esters?

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Why are amides less easy to hydrolyze than esters?

2006-09-07 11:19:22 · 3 answers · asked by openupthemic 3 in Science & Mathematics ➔ Chemistry

3 answers

There are a number of factors involved depending on the rest of the structure. The simplest way of looking at it is to think about how attractive the C=O carbon is too water molecules or nucleophiles. The O in esters is more electronegative than N in amides. That makes the C=O carbon in esters more "attractive" to water and other nucleophiles.

2006-09-07 13:10:14 · answer #1 · answered by Richard 7 · 0⤊ 0⤋

esters are more electronegative, so they're easier to hydrolize.

mmm...March's Orgo

2006-09-12 15:32:34 · answer #2 · answered by shiara_blade 6 · 0⤊ 0⤋

esters are shorter chains.

2006-09-07 18:24:39 · answer #3 · answered by voxninerbox 2 · 0⤊ 1⤋