September 16, 2019, 12:43:27 AM
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Topic: Alkene/Alcohol with Acid?  (Read 218 times)

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Offline sharbeldam

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Alkene/Alcohol with Acid?
« on: July 11, 2019, 07:34:53 PM »
(I know I have been asking alot, I promise Ill try not to ask again before september)

So this question is really confusing me, I have citronellol reaction (please look up the structure) with H2SO4/H2O, now citronellol has a double bond and an alcohol, so would the acid react with the double bond to give me diol product that will undergo an intramolecular reaction to give me a cyclic compound, or the acid would protonate the alcohol that already exists on the compound and dehydration will occur to give me another double bond (E2 dehydration since the alcohol is primary)?

Thanks alot in advance

Offline pgk

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Re: Alkene/Alcohol with Acid?
« Reply #1 on: July 12, 2019, 10:19:40 AM »
Whether dehydration or alcohol formation, it depends on the reaction conditions. E.g. excess of water favors alcohol formation, heat favors dehydration, high concentration and azeotrope conditions favor ether formation, on so on.

Offline hollytara

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Re: Alkene/Alcohol with Acid?
« Reply #2 on: July 12, 2019, 10:23:22 AM »
Absolutely correct - all depends on concentration of H2SO4 and temperature. 

Dilute H2SO4, low T - addition to alkene to make second OH
Concentrated H2SO4, high T - elimination of OH to form second alkene

Offline rolnor

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Re: Alkene/Alcohol with Acid?
« Reply #3 on: July 12, 2019, 10:28:05 AM »
I think you will get cyclization, addition of ROH to the double bond.

Offline sharbeldam

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Re: Alkene/Alcohol with Acid?
« Reply #4 on: July 12, 2019, 11:35:03 AM »
I honestly love this site and love you all, thanks alot <3

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