[onenameless]

I have a question here that shows the following attached.

Now i know the product is an ester, but the naming confused me a bit so here's what i tried to fiddle out:

O-benzylcarboxy ethanoic acid.

Is this correct?

[nj_bartel]

benzoic acid is the parent

salicylic acid is the common name

[macman104]

The base compound is benzoic acid.  So, we name the acetal group, so it becomes:

2-acetoxybenzoic acid

This is aspirin.

[nj_bartel]

2-hydroxybenzoic acid, that isn't aspirin 

[macman104]

2-hydroxybenzoic acid, that isn't aspirin 

He's asking for the name of the ester formed, aspirin

[onenameless]

Thank you 

[nj_bartel]

2-hydroxybenzoic acid, that isn't aspirin 

He's asking for the name of the ester formed, aspirin

Oh lordy.  I don't know why I can't manage to read through a whole question before I answer it muchless correct someone 

[aldoxime_amine]

Isn't that diagram highly misleading? The H of the alcohol and and the OH of the acid, should be present in the water...

[nj_bartel]

Not sure I understand completely what you're saying... But equilibrium for that specific carboxylic acid favors being protonated in water.

[aldoxime_amine]

What i am saying is that, in the esterification reaction, in the water formed, the oxygen belongs to the carboxylic acid.

[cliverlong]

My understanding of the esterification process between a carboxyl (acid) and a hydroxyl (Alcohol) group is that the carboxyl loses an OH and the alcohol just loses an H - contrary to the mechanism for an (Bronsted-Lowry) acid-base reaction - where the acid loses an H⁺. Water is eliminated in formation of ester bond.

Why? The lone pairs of electrons on the oxygen of the alcohol are attracted to the delta-negative carbon in the carboxyl (nucleophilic) group. This mechanism is more apparent when reacting an acyl-chloride (-COCl) with an alcohol, as HCl is eliminated. The presence of Cl in acyl chloride makes C in COCl more negative - and the source for the H in the elimiated HCl must have been the hydroxyl group, OH, in the alcohol.

Clive

[sjb]

My understanding of the esterification process between a carboxyl (acid) and a hydroxyl (Alcohol) group is that the carboxyl loses an OH and the alcohol just loses an H - contrary to the mechanism for an (Bronsted-Lowry) acid-base reaction - where the acid loses an H⁺. Water is eliminated in formation of ester bond.

Why? The lone pairs of electrons on the oxygen of the alcohol are attracted to the delta-negative carbon in the carboxyl (nucleophilic) group. This mechanism is more apparent when reacting an acyl-chloride (-COCl) with an alcohol, as HCl is eliminated. The presence of Cl in acyl chloride makes C in COCl more negative - and the source for the H in the elimiated HCl must have been the hydroxyl group, OH, in the alcohol.

True, there are isotopic labelling studies (using ¹⁸O, for instance) which show that the mechanism is as you propose. There is no guarantee that this mechanism operates all the time though.

S