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CHEM 313
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Chem 313, Problem Set #1, 2010 1. Determine whether or not the following amino acids are D or L, Also state the stereochemistry of each stereocenter as either R or S. CO 2 H I (S) H2N H H2N CO 2 (R) HO 2 NH 2 R (D) S (L) R (L) NH2 CF 3 HO 2 NH 2 (S) HO2C NH 2 H3C (S) (R) O (R) HO (R) SH O NH 3 S (L) side chain R R (D) side chain S R (L) 2. Explain the pKa trends for the following sets of molecules: H H H H H H pKa ~ 50 pKa ~ 15 N N pKa ~ 9 pKa ~ 5 N N N N H H Cyclopentane vs cyclopentadiene. 3 This question asks why the sp hybridize35H atom of the molecule on the right (cyclopentadiene) is way more acidic - 10 times! The cyclopentane is a general alkyl- anion that is not stabilized by anything. The cyclopentadiene upon losing an H becomes 2 sp hybridized and the lone pair interacts with the double bonds generating an aromatic species. The second part asks why the pyridinium is more acidic then the 4- dimethylaminopyridinium. Something stabilizes the conjugate acid on the right relative to the pyridinium. Both are in the same hybridization, have octets, and are aromatic. Therefore it must be resonance. N N N
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