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Unformatted text preview: CHEMISTRY 151.001L Fall 2006 Problem Set 6 1. One of the challenges in chapter 6 is being able to reorient molecules in your mind. For each of the pairs below, complete the drawing at the right by adding the two missing substituents at their correct positions to create the SAME molecule and the enantiomer and/or diastereomer. a. CH 2 CH 3 H 3 C H F H F same molecule enantiomer H F b. H F CH 2 CH 3 CH 3 H CH 2 CH 3 same molecule H CH 2 CH 3 enantiomer 2. Label each molecule as chiral, achiral or achiral/meso. Label each asymmetric carbon as R or S. H CH 3 HOH 2 C HO OCH 3 O CH 3 OCH 2 CH 3 H Cl Cl H 3 C H 3 C H 3 C CH 3 CH 3 H 3 C NH 2 CH 3 Br OH HO CHM 151 (HLS); Problem Set 6 2 3. Identify the following pairs of molecules as enantiomers, diastereomers, or the same molecule. Would a 50:50 mixture of each of the following pairs be optically active? a. H 3 C CH 2 OH H OH HO H CH 2 OH HO H CH 3 OH H _____________________ b. HO H HO H _____________________ c. CO 2 H Br H CH 3 H Br CO 2 H H Br CH 3 H Br _____________________ d. Br H 3 C H CN CN H Br CH 3 _____________________ 4. It has been shown that when Z-4-methyl-2-pentene is treated first with perbenzoic acid followed by ammonia, the major product is a 1/1 mixture of (2R, 3R)-2-amino-4-methyl-3-pentanol and its (2S, 3S) enantiomer. Is this process, the overall addition of H 2 N-OH across the double bond, net " syn " or net " anti "? Justify your answer with appropriate structures....
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