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Topic: Does the mechanism look right?  (Read 661 times)

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Offline sharbeldam

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Does the mechanism look right?
« on: September 03, 2020, 07:31:25 PM »
I mean after the 1,4 addiction, i could get ketone and then the diol could form acetal (protecting group) which would prevent me from reaching my final product right?

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Offline phth

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Re: Does the mechanism look right?
« Reply #1 on: September 03, 2020, 11:55:57 PM »
No,
The diol reacts with the ketone after the Gliman reaction (this is correct). Both steps are separate reactions. The ketone turns into a ketal (a base stable protecting group). Practice The mechanism then check the answerhttps://www.google.com/search?q=ketal+ethylene+glycol+mechanism&rlz=1C1CHBF_enUS901US901&oq=ketal+ethylene+glycol+mechanism&aqs=chrome..69i57j33l3.6020j0j7&sourceid=chrome&ie=UTF-8

Offline kriggy

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Re: Does the mechanism look right?
« Reply #2 on: September 04, 2020, 01:37:27 AM »
Activating primary alcohols in this manner is not feasble AFAIK (ie. forcing the water to leave like this). If you want to make your product you need a compound that is going to be electrophilic at the carbon. This means synthon like

C+H2-CH2-OH

can you think of any compounds that could reaact like this?

Offline sharbeldam

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Re: Does the mechanism look right?
« Reply #3 on: September 04, 2020, 04:26:15 AM »
Thank you!! i should get acetal in the end yes
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