HW13Key - OCH 2 CH 3 1 NaOEt EtOH 2 H 3 O H O O H OEt Propose a mechanism for the overall transformation shown above As usual use curved arrows to

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Graded Homework Problem #13 – Answer Key Deadline : 3:00 p.m., Thursday, 3/31/07 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. One of the steps involved in an early synthesis of cholesterol involved the crossed Claisen condensation reaction shown below. Please note that the “squiggly” bond in the product indicates that the new chiral center created in the reaction is formed having both possible stereochemical configurations H O + O H
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Unformatted text preview: OCH 2 CH 3 1) NaOEt, EtOH 2) H 3 O + H O O H + OEt Propose a mechanism for the overall transformation shown above. As usual, use curved arrows to show movement of electron pairs, and draw structures for all important reaction intermediates. If an intermediate is a resonance hybrid, it is only necessary to draw the most important contributing resonance structure. H O H O H OCH 2 CH 3 H O O H H OEt H O H O O OCH 2 CH 3 H OEt H O O H OEt H OEt H O H H H H O O H H O H H...
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This note was uploaded on 04/30/2008 for the course PHY 317L taught by Professor Ritchie/lang during the Fall '08 term at University of Texas at Austin.

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