Final - Chemistry 0320 Final Examination December 13, 2008...

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1 Chemistry 0320 Final Examination December 13, 2008 Name: _____________________________ 1. Provide an example that fits the following descriptions. (15 points) a) A Boc-protected amine. b) An activating group for electrophilic aromatic substitution. c) An α -amino acid. d) A terminal alkyne. e) A tertiary amine.
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2 2. Provide brief explanations for the following observations. Explanations will be most effective if structures are included in your answers. (40 points) a) The Diels-Alder reaction shown below gives only A and not B . b) β -keto ester C can be alkylated by MeI after deprotonation by NaOEt to provide D . Exposing ethyl acetate ( E ) to the same conditions results in no alkylation reaction. NMe 2 + O OEt Me 2 N OEt O not OEt O Me 2 N A B ! O OEt O 1. NaOEt 2. MeI O OEt O C D OEt O 1. NaOEt 2. MeI E no reaction
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3 c) Compound F undergoes S N 1 reactions much more quickly than compound G . d) Transesterification of ester
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This note was uploaded on 05/17/2010 for the course CHEM 0740 taught by Professor Professor during the Spring '10 term at Pittsburgh.

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Final - Chemistry 0320 Final Examination December 13, 2008...

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