Ochem Question (Acid/Base)

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Hi guys,

I'm needing some help understanding the answer to this question.

SO I sort of understand their explanation....But I'd like to figure out why my original rationale was wrong.

My original rationale was that since NaOH is a STRONG BASE it would like to dissociate itself and hence in reaction B would prefer to shift right.

And in Reaction C since carboxylic acid is a Weak Acid it doesn't really want to go forward as much into the product side and hence favors the reactant side.

Can anyone explain to me why this way of thinking is wrong?

Thank you!

 

[iq DAT]

I will suggest a different approach to this question. You and the explanation are correct in thinking acid base terms for options a and d. Going from stronger to a weaker acid or base will drive the equilibrium to the right. I would then switch to a more organic chemistry mindset to see if b or c is the correct answer. Option c a carboxylic acid hydrogen forming a C-H bond in the ester. This is a relatively favorable process, which will make the ester more stable. Option b breaks off a hydrogen from ethane (not very likely) to add it to the OH of NaOH and form water.

Try to get rid of the Na+ and write a more "organic chemistry" type reaction and I think you will get a better idea of what is happening. You will notice that c) has carbanion in the products and b) has a carbanion in the reactants.

 

[LetsGetSocial]

Thank you for the explanation! Makes sense 🙂