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Alcohols and esterification? - October 26th 2009, 12:44 AM

Hey everyone... Gotta quick question for you. I just cannot figure out the answer to this.

Why do primary alcohols react faster then secondary alcohols during the esterification process? (the formation of esters)

Any help is much appreciated!
   
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Re: Alcohols and esterification? - October 26th 2009, 04:39 AM

I suppose that it may have to do with the 3-D organization of the molecules. For a secondary alcohol, the -OH group may be harder for the other reactant to get to, whereas for a primary alcohol, the -OH group is much easier. If you try to think about the angles for the bonds, the primary alcohol's -OH group would have a larger angle and so it'd be easier for the other reactant to bind to.
Another reason, which builds upon the idea above, is that there would be a difference in the energy barrier to overcome, that is, the secondary alcohol would have a higher energy barrier. Lastly, for a secondary alcohol, such as isopropyl alcohol, HC-OH part of the molecule may produce a somewhat less stable intermediate product.
   
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Re: Alcohols and esterification? - November 2nd 2009, 02:44 PM

^ I disagree - It's pretty much a matter of sterics, secondary alcohols are bigger and therefore it's harder for them to undergo nucleophilic attack.
   
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