Chem 317 - Set 5 extra problem solutions

Chem 317 - Set 5 extra problem solutions - 1. Design an...

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HO NH 2 NH 2 N O NH O 1. Design an experiment using amine basicity to determine if a substituent Z is electron-donating or electron-withdrawing by induction only or by resonance and induction. Describe what you should observe in your experiment for all possibilities of Z. Inductive effects could be tested by putting substituent Z on C-2 of ethanamine: a. Which is the stronger base? b. Which is the stronger base? or C D or NH 2 NH 2 Z NH 2 Z Z NH 2 NH 2 A The OH group is electron withdrawing by induction, weakening the basicity of 2-aminoethanol. B E The lone pair of electrons on N cannot be parallel to the carbonyl pi bond, so the compound is not chemically an amide! The N has the basicity of a regular amine. The second structure alone has resonance donation of the lone pair from N to the carbonyl carbon. 2. For the following, answer the question and briefly explain: Comparing D to C tests the inductive effect of Z, as meta substituents can exert only an inductive effect. If Z is electron-donating by induction, D will be a stronger base than C; if Z is
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This homework help was uploaded on 04/09/2008 for the course CHEM 317 taught by Professor Kantorowski during the Fall '08 term at Cal Poly.

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Chem 317 - Set 5 extra problem solutions - 1. Design an...

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