Exam3-2009

Exam3-2009 - Name _ 1. (16 pts) Draw the...

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Name __________________________ 1. (16 pts) Draw the structures specified in parts a - g. a. An α , β -unsaturated aldehyde of molecular formula C 4 H 6 O c. N -Ethyl-3-hexanamine d. 4-Methylpyridine e. 3-Pyrrolecarboxylic acid f. 2,4-Dimethoxypyrimidine g. A secondary amine of molecular formula C 4 H 9 N. b. The enol and enolate derived from 2-acetylfuran O O H 3 O + OH - page 1 O O O or or O O O OH HN N CH 3 N H CO 2 H N N OCH 3 OCH 3 N H or N H H N or NH or and others
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2. (6 pts) The pKa values associated with the structures shown below are 9, 11, 15. Write the correct pKa value in the space below each compound. 3. (6 pts) The conjugate acids of the heterocycles listed below have pKa values of 1.10, 5.14, and 9.17. Write the correct pKa value in the space below each compound. pKa N N N N NH 2 4-Aminopyridine is protonated on the ring nitrogen rather than on the exocyclic amino group. Use resonance theory to explain this preferred site of protonation. N O O EtO O O O O pKa i. ii. iii. i ii. iii. Draw the structure of the enolate obtained when iii. is treated with sodium ethoxide. Show all reasonable resonance structures. Name __________________________ page 2 9 11 15 EtO O O EtO O O EtO O O 1.10 5.14 9.17 N NH 3 Protonated amino destabilized by electron withdrawing effect of C=N N NH 2 H N NH 2 H Stabilized by resonance
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5. (6 pts) When compound
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This note was uploaded on 03/30/2011 for the course MCMP 205 taught by Professor Staff during the Spring '08 term at Purdue.

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Exam3-2009 - Name _ 1. (16 pts) Draw the...

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