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CH 310M/318M Spring 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Please circle the section in which you are registered ! POINTS MAY BE DEDUCTED IF YOU DON’T ! MWF 9:00 TTh 8:00 Graded Homework Problem #19 Deadline : 3:00 p.m., Monday, 4/28/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. When the S N 2 reaction mechanism occurs at a chiral center, complete inversion of the stereochemical configuration is observed. When the S N 1 reaction mechanism occurs at a chiral center, racemization is observed. The nucleophilic substitution reaction shown below occurs with complete retention of the stereochemical configuration! H 3 C O H Br H O OH a resonance hybrid - DRAW 1 IMPORTANT RESONANCE STRUCTURE!!! OH + H OH molecular formula = C 3 H 4 O 2 Br + a resonance hybrid - DRAW 1 IMPORTANT
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Unformatted text preview: RESONANCE STRUCTURE!!! H O H H H 3 C O H O H H O + H OH O H Br H O 1) NaOH, H 2 O 2) H 3 O + O H O H H O + Na Br The mechanism of this overall transformation is outlined in the reaction scheme given. Complete this mechanism by drawing curved arrows to show movement of electron pairs in each step. Draw structures of all important reaction intermediates in the large boxes. (The other product is also drawn in the large box if it DOES NOT react further.) BE SURE TO SHOW STEREOCHEMISTRY CLEARLY AND UNAMBIGUOUSLY in all of the structures that you draw! Two of the important reaction intermediates are resonance hybrids it is only necessary for you to draw one of the important contributing resonance structures....
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