Why is there a need to use excess acid in the dehydration of alcohols? My instructor said that excess acid is necessary to minimize the ether formation via the competing SN2 mechanism, but I'm not sure how this works.
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asked Jul 29, 2017 at 15:13
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1$\begingroup$ Acid is catalyst so I don't see here any meaning in "excess" $\endgroup$– MithoronCommented Jul 29, 2017 at 15:39
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1$\begingroup$ @Mithoron Well, excess sulphuric acid would obviously assist in dehydration. Probably, it would even make dehydration faster than etherification. $\endgroup$– JanCommented Aug 19, 2017 at 15:00
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1 Answer
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Alcohols generally are very poor acids and have pka's in the range of 16-17.
Hence, if the medium is only slightly acidic, only some alcohols will protonate, after which the unprotonated oxygen (of ROH) will attack the generated carbocation, following which the H+ ion will leave making H+ act as a catalyst, resulting in the formation of ether.
But, if the solution is highly acidic, we would be generating the carbocation in full and there would be no nucleophile left to attack the carbocation.
We need to maintain the optimum pH as substitution reactions are generally favoured over elimination reactions especially in the case of primary and secondary alcohols.
