[arooga]

How many mmol of HCl would be required at the minimum to completely hydrolyze 2 mmol of methyl acetate?

I know for base-catalyzed hydrolysis of esters, each mole of ester hydrolyzed requires 1 mole of base.

According to the mechanism of acid-catalyzed hydrolysis of esters from this source, http://www.mhhe.com/physsci/chemistry/carey/student/olc/graphics/carey04oc/ref/ch20reactionsesters.html, is it safe to conclude that 2 moles of acid are required to hydrolyze each mole of ester?

Thank you

[Dan]

is it safe to conclude that 2 moles of acid are required to hydrolyze each mole of ester?

I'm afraid not. Can you explain how you came to this conclusion? Start with the absolute basics:

MeCOOMe + ^-OH ---> ?

and

MeCOOMe + H₃O⁺ ---> ?

and reconsider the problem.

[Arene]

The mechanism uses two moles of acid to catalyze the reaction I believe.

[Dan]

The mechanism uses two moles of acid to catalyze the reaction I believe.

You miss the point as well.

Complete the balanced equations I started. It is not actually necessary to know the mechanism is A_AC2 to answer the question - acid/base equilibria is the key. I think it's a bad question actually.

[Arene]

I guess I do. I would love to learn.

MeCOOMe + OH-  ---> MeCOO + MeOH

MeCOOMe + 2H3O+ --> MeCOOH + MeOH + H3O+

[Arene]

It looks like it is catalyzed by two hydronium, yet mechanistically one returns to solution. Is this reflected properly in the equations above?

[Dan]

Ok, careful with your balancing.

I guess I do. I would love to learn.

MeCOOMe + 2OH-  ---> MeCOOH + MeOH + OH-

This is not balanced (charges are 2- on the left and 1- on the right) - to make life easier, two hydroxides are not necessary.

MeCOOMe + 2H3O+ --> MeCOOH + MeOH + H3O+

Again, not balanced (charges) - two hydroniums are not required

[Arene]

thank you. I completely ignored the charges.