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POW-310-7-Key - O H H Protonated Hemi-acetal...

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Last Name: UTEID: First Name: SCORE: KEY Deadline for POW 310-7: Mar 9, 2009 3:00 PM 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. H 3 O + 2 o Carbocation Protonated acetal (or ketal) Hint: this is a nucleophilic attack of water upon the carbocation H 2 O H ~ H note: this symbol can be used to indicateproton transf ers Protonated Hemi-acetal Structure (protonated on hydroxyl oxygen) #1 H 3 C C H 2 CH 3 O H 3 C C H 2 CH 3 O O H 3 C C H 2 CH 3 O O O CH 2 CH 2 OH H 3 C C H 2 CH 3 HO H O CH 2 CH 2 OH H 3 C C H 2 CH 3 HO O CH 2 CH 2 H 3 C C H 2 CH 3 OH H 3 C C H 2 CH 3 O O
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Unformatted text preview: O H H Protonated Hemi-acetal Structure (protonated on ether oxygen) Continued on next page #2 #3 #4 Hint: this is a ring opening step OH CH 2 H 2 C HO + Neutral Ketone Final Product H 3 C C H 2 CH 3 O O CH 2 CH 2 OH H 3 C C H 2 CH 3 O H Protonated Hemi-acetal Structure (protonated on ether oxygen) same structure as in #4 H O CH 2 CH 2 OH H 3 C C H 2 CH 3 O H 2 o Carbocation (resonance stabilized) H H this is the loss of neutral ethylene glycol #4 #5 this is the loss of a proton...
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