Does the total number of carbons in an ester affect its Kc of hydrolysis?

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The discussion centers on a research experiment involving the equilibrium constants (Kc) of various esters in the presence of water and concentrated HCl. The experiment revealed that esters with a higher number of carbon atoms exhibited lower Kc values, although the relationship was not strictly proportional. The researcher seeks to understand the underlying reasons for this trend and whether it could be a coincidence. Participants in the discussion question the accuracy of the Kc measurements and suggest considering the possibility of confusion with reaction kinetics. The conversation emphasizes the need for clarity in distinguishing between equilibrium constants and kinetic factors in chemical reactions.
nnoor
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Hello!

I am currently writing a research paper. I performed an experiment whereby I left 5 esters of different overall number of carbons (methyl benzoate, ethyl acetate, ethyl formate being 3 examples) in presence of water and concentrated HCl to reach equilibrium (in 9 days). I then titrated the solution against NaOH and did subsequent calculations to derive the equilibrium constant (Kc) values of each ester. What I found was rather interesting: the more carbons an ester has, the lower the Kc value, though not proportionally so. The experiment was done under standard conditions.

My question is, is there any particular reason or justification as to why this is so? Or was this rather just a fluke?

I appreciate any ideas of suggestions you have. Thank you!
 
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Are you sure you have measured Kc, and not reaction kinetics?

It is not to say that your observation is wrong.
 
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