hw 4 - N-protonated N H H 3 C OCH 3 O Tetrahedral...

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Last Name: UTEID: First Name: SCORE: KEY Deadline for CH310N HW 4, Due: Oct 10 3:00 PM Mechanism: Provide a mechanism for the following transformation. Show all important flows of electrons, charges and intermediates. Where indicated, (in the structure-n-a- box)- draw the intermediates. OCH 3 O H + H 3 C OCH 3 O H Show the nucleophilic attack by piperidine Show the loss of methanol and the formationof the amide Protonate the ester HN H 3 C OCH 3 O N O +CH 3 OH + TsOH (cat) heat HN piperidine H 3 C OCH 3 OH Tetrahedral intermediate with
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Unformatted text preview: N-protonated N H H 3 C OCH 3 O Tetrahedral intermediate with O-protonated N H H Intramolecular proton transfer N O + CH 3 OH O 3 S A) B) C) O CH 3 Retrosynthesis: Each of the following-unsaturated ketones can be produced from an aldol condensation-dehydration reaction. Provide the starting material(s) for the preparation of each compound. O O O H H 3 C O CH 3 O H O CH 3 CHO O CH 3...
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This note was uploaded on 10/20/2011 for the course CH 310 N taught by Professor Blocknack during the Fall '08 term at University of Texas.

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hw 4 - N-protonated N H H 3 C OCH 3 O Tetrahedral...

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