Kaplan Orgo question - esterification & hydrogen bonding

[Vicodin_]

From kaplan orgo book Ch.9 practice question, #15

Why would extensive hydrogen bonding of water augment nucleophilic substitution reaction (esterification)? I thought more hydrogen bonding to carboxylic acid would hinder the molecule interfere with the reaction.

Thanks!

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[theonlytycrane]

It's similar to how acid would protonate the carbonyl oxygen and make the electrophilic carbon more positive, except to a lesser extent (through only hydrogen bonding).

 

[MDHopefulIA]

Hydrogen bonding with water would not interfere the nucleophilic addition mechanism a. carboxylic acids undergo nucleophilic substitution because remember there is usually a leaving group (my book says nucleophilic addition in the answer) b. because the nucleophilic attack is on the carbonyl carbon, not the carbonyl oxygen or OH (both are where the hydrogen bonding is occurring) c. the hydrogen bonding with the water could, in effect, pull that carbonyl oxygen and OH and their respective electron density with the hydrogen bonding by creating those intermolecular attractions b/w them and the water , thus making the carbonyl carbon more electrophilic and positive as theonlytycrane said and more susceptible to nucleophilic attack.