Chem 35 Practice Problems 4.2.2008

Chem 35 Practice Problems 4.2.2008 - Chem 35 Practice...

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April 2, 2008 1. Ascorbic Acid a) Ascorbic acid (Vitamin C), which is drawn below, is actually a fairly strong organic acid (pKa ~ 4.17) despite the fact that it contains no carboxylic acid functionality. Which proton is most acidic, represented by the aforementioned pKa? Which proton is next most acidic? Rationalize your answer using arguments of acidity/basicity that you have learned. b). Identify all of the stereocenters in ascorbic acid above. Draw out all of the possible stereoisomers of this compound, and name each of the stereogenic centers R or S. 2. Identify the most basic pair of electrons (within each molecule) in the compounds shown below, and draw out the Lewis structure of their corresponding conjugate acids. N NH 2 O NH N H N O O - 3. Epoxides a). The epoxide shown in the center of the diagram below could hypothetically be formed via an intramolecular S N 2 reaction between the alcohol and alkyl bromide in either of the two starting compounds. However, one isomer reacts much faster than the other. Provide an explanation for
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This note was uploaded on 04/29/2008 for the course CHEM 35 taught by Professor Seto during the Fall '07 term at Brown.

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Chem 35 Practice Problems 4.2.2008 - Chem 35 Practice...

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