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Chem 222 Chapter 5 homework

Chem 222 Chapter 5 homework - R-3-bromo-3-methylcyclohexane...

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Chem 222 Chapter 5 Homework 1. Assign R or S stereochemistry to stereocenters in the following molecules: CH 3 H Cl F a. Br H 3 CO Cl CH 3 H 3 C H CH 2 F Cl Cl H O OH H CH 3 b. c. d. e. 2. Consider the structure of the (-)-lyxose below. It’s specific rotation is -13.8º. H HO H HO OH H CH 2 OH CHO a) What functional groups are present? b) How many stereocenters are in the molecule? c) How many stereoisomers are possible? d) Label the stereocenters as R or S e) Draw the enantiomer of (-)-lyxose f) Predict the specific rotation of the enantiomer. g) Draw a diastereomer of (-)-lyxose. h) Are any optically inactive diastereomers of (-)-lyxose possible? If there are draw them. 3. Which of the following are meso compounds? Cl Cl Cl Cl H H a. b. c. OH H H HO CH 2 OH CH 2 OH CH 2 OH OH H H HO H HO OH H CH 2 OH d. 4. Draw structures of the following molecules using both perspective drawings and Fischer projection formulae. (a) ( R )-2-chloropropane (b) ( S )- 2-methyl-3-bromohexane (c) (3R,5 S )-3,5-dimethylheptane (d) (
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Unformatted text preview: R )-3-bromo-3-methylcyclohexane. 5. In the radical monochlorination of the molecule below at the positions labeled with an asterisk (*), (a) If more than one stereoisomer is formed at each position indicate if they are in equal or unequal amounts? (b) assign R or S stereochemistry to each chiral center of the product. CH 2 CH 3 CH 2 CH 2 Cl Cl H * * * 6. What is the relationship between the two compounds below (diastereomers, enantiomers, constitutional isomers, identical compounds)? Draw Newman projection formulae to represent the compounds in a staggered conformation. Br Br H H Br H Br H and 7. Indicate whether each of the following structures represents ( R )-2-chlorobutane or ( S )-2-chlorobutane. Cl H 3 CH 2 C H CH 3 Cl H H 3 C H Cl CH 3 H a) b) c)...
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