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Topic: Mechanism with cat H2SO4  (Read 286 times)

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Offline kimmy123

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Mechanism with cat H2SO4
« on: November 01, 2021, 02:27:48 PM »
I am having trouble with a mechanism that asks to convert a five-membered ring into a six-membered ring using catalytic H2SO4.
I first begin with lone pair on the O (of OH) grabbing one H from H2SO4. Then the H2O leaves leaving behind a + sign. A bond on the ring then breaks to attach to the carbon, forming the six-membered ring. However, afterwards, I am unsure how to proceed.

Offline rolnor

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Re: Mechanism with cat H2SO4
« Reply #1 on: November 01, 2021, 03:15:57 PM »
 An you draw the scheme+mechanisms you have figured out?

Offline kimmy123

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Re: Mechanism with cat H2SO4
« Reply #2 on: November 01, 2021, 03:25:06 PM »
An you draw the scheme+mechanisms you have figured out?

Offline rolnor

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Re: Mechanism with cat H2SO4
« Reply #3 on: November 02, 2021, 05:33:46 AM »
Your mechanism is wrong in some places, if you look at the ketone carbonyl in the final product, where can this be found in the startingmaterial? Look at the carbon connected to the hydroxymethyl carbon in the startingmaterial.

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