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posted by  mickey1 on 11/3/2009 2:38:20 PM  |  status: Closed  |  Earned Karma: 35

stuck with ochem...rate lifesaver

Course Textbook Chapter Problem Needs by
Organic Chemistry N/A N/A N/A 11/4/2009 at 12:00:00 PM
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holla!

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posted by nomorephysics on 11/3/2009 3:18:22 PM  |  status: Live
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a)   
b)  There is steric hinderance by the methyl groups here that prevent the reaction from taking place.  The methyl groups block the lone pair on the nitrogen from reacting.
nomorephysics
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posted by sekushii on 11/3/2009 3:32:09 PM  |  status: Live
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a) -OH becomes a good leaving group by being activates by the thionyl chloride. Because it is a primary group, it can readily undergo Sn2 reactions, even with the base (pyridine).



b) 2,6-lutidine is so bulky that is cannot substitute the -OSOCl leaving group in an Sn2 reaction. Even though it has lone pairs on the N available for nucleophilic attack, the adjacent methyl groups hinder access of the activated alcohol.
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