POW-318-5-key - (this intermediate will loose H 2 O) + H...

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Last Name: UTEID: First Name: SCORE: KEY POW 5 CH 318N Due October 5, 2009 Mechanism: Provide a mechanism for the following transformation. Show all important flows of electrons, charges and intermediates. Where indicated, (in the structure boxes)- draw the intermediates. CH 3 O HOCH 2 CH 2 OH CH 3 H 2 O/ H 3 O + (catalytic) O CH 2 H 2 C O CH 3 O H HO OH CH 3 OH O OH CH 3 OH O OH CH 3 OH Neutral Hemiacetal Tetrahedral Intermediate O OH CH 3 OH 2 Protonated ketone intermediate First Step Hint: this is a loss of a proton Protonated Hemiacetal
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Unformatted text preview: (this intermediate will loose H 2 O) + H Hint: next step is the nucleophilic attack of ethylene glycol-use one of the oxygen atoms Hint: this is a proton transfer- H H H continue on next page O OH CH 3 CH 3 O CH 2 H 2 C O CH 3 O CH 2 H 2 C O-H 2 O Carbocation intermediate Hint: this is an intramolecular ring closure Protonated Acetal-H Product: acetal H Hint: this is a loss of a proton...
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POW-318-5-key - (this intermediate will loose H 2 O) + H...

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