Action Center 10 Stereochemistry 2

Action Center 10 Stereochemistry 2 - same meso compound or...

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Action Center Practice Problem – Stereochemistry 2 (Klein: Chapter 5) Sections Covered: 5.4-5.9 1. (–)-Menthol can be isolated from the peppermint plant and is responsible for the characteristic Favor and taste of peppermint. (–)-Menthol is optically active, its speci±c rotation [ α D ] = –58˚. The structure of (–)- menthol is shown below. The instructional lab purchase a bottle of menthol at a large discount. When the bottle arrived it was not labeled as (–)-menthol. A sample from this bottle gave an observed rotation of –12˚ at 20˚C. Calculate the %ee of the contents of the bottle labeled as just menthol. What percentage of (–)-menthol is in the container. 2. For the following pairs, label each set as either enantiomers, diastereoisomers, two conformations of the
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Unformatted text preview: same meso compound, or identical chiral molecules. A) OH OH D ) B) E ) Br Br C) HO OH F ) Br Br Br Br 3. Provide the stereochemical designations (R or S) for the indicated chiral centers in the following molecules. H CH 3 CH 2 CH 3 OH * OH H H HO CH 2 OH H O * * 4. The structure below is known by its common name, riesling acetal. Two of the stereoisomers of this compounds have been isolated as one of the many compounds leading to the aroma of wines as they age. The (+)-(1S, 6R, *S)-riesling acetal has a woody, fruity, and flowery note while the (–)-(1R, 6S, 8R)-riesling acetal has a slightly camphoraceous note. How many stereoisomers are possible for riesling acetal structure? O O...
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