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Chapter 4: Isomers: The Arrangement of Atoms in Space

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Page 184

Question:What is the configuration of the asymmetric centers in the following compounds?

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Page 149

Assign relative priorities to each set of substituents:

a. -Br -I -OH -CH3

b. -CH2CH2OH -OH -CH2Cl -CH=CH2

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Page 185

Question:

a. Draw all the isomers with molecular formula C6H12 that contain a cyclobutane ring. (Hint: There are seven.)

b. Name the compounds without specifying the configuration of any asymmetric centers.

c. Identify

1. constitutional isomers 2. Stereoisomers 3. cis鈥搕rans isomers 4. chiral compounds

5. achiral compounds 6. Meso compounds 7. Enantiomers 8. diastereomers

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Page 185

Question:A compound has a specific rotation of -39.0. A solution of the compound (0.187 g/100 mL) has an observed rotation of -6.52掳 when placed in a polarimetertube 10 cm long. What is the percent of each enantiomer in the solution?

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Page 185

Question: Draw structures for each of the following:

a.(S)-1-bromo-1-chlorobutane

b.(2R,3R)-2,3-dichloropentane

c.an achiral isomer of 1,2-dimethylcyclohexane

d.a chiral isomer of 1,2-dibromocyclobutane

e. two achiral isomers of 3,4,5-trimethylheptane

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Page 185

For each of the following structures, draw the most stable chair conformer.

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Page 185

Explain why the enantiomers of 1,2-dimethylaziridine can be separated even though one of the 鈥済roups鈥 attached to nitrogen is a lone pair.

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Page 185

A sample of (S)-(+)-lactic acid was found to have an enantiomeric excess of 72%. How much Risomer is present in the sample?

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Page 185

a. Using the wedge-and-dash notation, draw the nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane.

b. From the nine stereoisomers, identify one pair of enantiomers.

c. Draw the most stable conformer of the most stable stereoisomer.

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Page 185

What is the configuration of each of the asymmetric centers in the following compounds?

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