hydrolyse of compounds

[gin]

I would like to ask about which of these compounds hydrolyse at the fastest and slowest rate?

 

1.Acid chloride

2.Amide

3.Anhydride

4.Ester

 

I'm not sure if its ester or anhydride hydrolyses at slowest rate.

 

Thanks

[big314mp]

Draw the resonance structures of the Anhydride and the ester, and look to see which has more positive charge on the carbonyl compound. The more positive the carbonyl carbon, the more reactive the species.

 

Draw the resonance for the amide too.