test III key_223_fall 07

test III key_223_fall 07 - 1 Chemistry 223 Organic...

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Chemistry 223 Organic Chemistry II Test III_ key November 14, 2007 Dr. Latifa Chahoua (6 pt)1. Provide the IUPAC names for the following molecules. a) b) c) a) 2,4-hexanediamine b) N -ethylaniline c) Methyl-2-aminobutanoate (10 pt) 2. Circle the major product of these two reactions. Explain why and provide a mechanism for its formation. a) Assuming that the Ph is bulkier than CH 3 CO in this reaction. This statement is helpful after you choose the α hydrogen. If you remove the α hydrogen close to the Ph, the anion formed is stabilized by resonance with the benzene ring that leaves you with compound A or B . Since we assumed that Ph is bulkier than the CH 3 CO, then A will be the major compound. NaOCH 3 CH 3 OH Ph O Ph Ph Ph O O O Ph Ph Ph A B C H H - OCH 3 Ph O - CH 3 OH Ph O Ph O Ph O - H Ph O Ph OH H b) The carbonyl group in the starting material has two kinds of α hydrogens: the methyl and the isopropyl and are of almost of equal acidity. LDA is bulky base, therefore the least hindered α hydrogen is going to be removed in preference and that is the methyl hydrogen. The major product is the E .
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This note was uploaded on 04/08/2008 for the course CHEM 223 taught by Professor Chahoua during the Fall '07 term at Wake Forest.

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test III key_223_fall 07 - 1 Chemistry 223 Organic...

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