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Unformatted text preview: [(1-ethyl-1-methylpropyl)cyclopentane] cis-1,1,2,3-tetramethylcyclopropane 3-ethyl-7-methylnonane amine amide aromatic The amine nitrogen is more basic (circled above); the major factor: the e l e c t r o n d e n s i t y o f t h e a m i d e n i t r o g e n i s l o w e r a t n i t r o g e n b e c a u s e o f d e l o c a l i z a t i o n t o t h e c a r b o n y l o x y g e n and (to a lesser extent) because of delocalization into the adjacent benzene ring. To a lesser extent, inductive bond polarization also contributes: the alkyl group substituents on the amine nitrogen donate electron density (increasing basicity); the carbonyl oxygen withdraws electron density (by bond polarization) to further decrease basicity there. Finally, anyone may be asked to change seats at any time during the exam - if asked to do so, please move to the new seat location as expeditiously as possible....
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This note was uploaded on 02/28/2012 for the course CHEM 210-1 taught by Professor Trzupek during the Fall '08 term at Northwestern.
- Fall '08