Chem210-1 F08 Ex1 p01a

Chem210-1 F08 Ex1 p01a -...

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1. Provide an acceptable name for each of the compounds below (3 pts each) a) b) c) 2. The structure of the local anesthetic lidocaine is shown on the right: C CH 3 CH 2 -CH 3 CH 2 -CH 3 H Cl Cl H Cl Cl CH 3 CH 3 H N C O CH 2 N CH 2 H 3 C CH 2 CH 3 a) In which functional families could lidocaine be classified? (what functional groups are present in the lidocaine structure? - be sure to specify them all) (3 pts) b) Lidocaine is usually used in a salt form which could be obtained by reacting the molecule (with the structure above) with 1 equivalent of H-Cl. That reaction leads to the preferential protonation of only 1 of the two nitrogens in the lidocaine structure - the one with the greatest electron density. Which of the two nitrogens will get protonated (circle it), and WHY (you can provide several reasons, but you'll lose credit for any incorrect reasoning, and will get full credit only if your answer includes the most important reason). (6 points) 3-cyclopentyl-3-methylpentane
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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.

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