CHEM 2323 Handout #5 - Stereochemistry.doc

CHEM 2323 Handout #5 - Stereochemistry.doc - CHEM 2323...

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Unformatted text preview: CHEM 2323 Organic Chemistry I Handout #4 – Stereochemistry 1. Is the molecule shown below chiral or achiral? (CH3)3CCH(CH3)2 2. Is the molecule shown below chiral or achiral? CH3CH2CH(CH3)CH2CH3 3. Is the molecule shown below chiral or achiral? 4. Is the molecule shown below chiral or achiral? 5. Is the molecule shown below chiral or achiral? 6. Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound? 7. Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound? 8. Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound? 9. Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound? 10. Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound? 11. Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound? 12. Label each asymmetric carbon in the compound below as R or S. 13. Label each asymmetric carbon in the compound below as R or S. 14. Label each asymmetric carbon in the compound below as R or S. 15. Label each asymmetric carbon in the compound below as R or S. 16. Draw the structure of (2R,3S)-2,3-dichloropentane. Take particular care to indicate three-dimensional stereochemical detail properly. 17. Draw the structure of any diastereomer of (2S, 3R)-2,3-dichloropentane. Take particular care to indicate three-dimensional stereochemical detail properly. 18. Draw the structure of the meso form of 1,3-dichlorocyclopentane. Take particular care to indicate three-dimensional stereochemical detail properly. 19. How many asymmetric carbons are present in the compound below? 20. Can the molecule shown below be properly described as a meso compound? (CH3)2CHCH2CH3 21. Can the molecule shown below be properly described as a meso compound? 22. Draw the structure of (1R, 2S, 3S)-1,2-dibromo-3-ethylcyclohexane. Take particular care to indicate stereochemistry properly. 23. __________ are isomers which have the same bonding sequence but differ in the orientation of their atoms in space. 24. Which of the statements below correctly describes an achiral molecule? A) The molecule has a nonsuperimposable mirror image. B) The molecule exhibits optical activity when it interacts with plane-polarized light. C) The molecule has an enantiomer. D) The molecule might be a meso form. E) None of the above 24. Which of the following statements correctly pertains to a pair of enantiomers? A) They rotate the plane of polarized light by exactly the same amount and in opposite directions. B) They rotate the plane of polarized light by differing amounts and in opposite directions. C) They rotate the plane of polarized light by differing amounts and in the same direction. D) The have different melting points. E) They have the same melting point, but they have different boiling points. 25. Stereoisomers which are not mirror image isomers are __________. 26. A mixture of equal amounts of two enantiomers __________. A) is called a racemic mixture B) is optically inactive C) implies that the enantiomers are meso forms D) both A and B E) none of the above 27. Can a molecule be chiral if it contains no asymmetric carbons? Explain briefly. 28. If the absolute configuration at an asymmetric carbon does not change during the course of a reaction, the reaction is said to occur with __________ of stereochemistry. 29. Which of the following statements is (are) true for the compound (R)-2-butanol? A) This compound is chiral. B) This compound is optically active. C) This compound has an enantiomer. D) all of the above E) none of the above 30. Which of the following statements is (are) true for the compound (3R, 4R)-3,4-dimethylhexane? A) This compound is chiral. B) The enantiomer of this compound is (3S, 4S)-3,4-dimethylhexane. C) This compound is a diastereomer of (3R, 4S)-3,4-dimethylhexane. D) all of the above E) none of the above 31. Which of the following terms correctly describe(s) the structural relationship between cis-1,3-dimethylcyclopentane and trans-1,3-dimethylcyclopentane? A) enantiomers B) diastereomers C) geometric isomers D) both A and C E) both B and C 32. Does the molecule shown below contain asymmetric carbon atoms? Is this molecule chiral? 33. Draw the Fischer projection of (S)-2-hydroxybutanoic acid, CH3CH2CH(OH)COOH. 34. How many diastereomers are there of the molecule shown below? A) 0 B) 1 C) 2 D) 3 E) 6 35. How many diastereomers are there of the molecule shown below? A) 0 B) 1 C) 2 D) 3 E) 6 36. How many enantiomers are there of the molecule shown below? A) 0 B) 1 C) 2 D) 3 E) 6 37. If possible, draw the structure of the enantiomer of the molecule shown below. 38. If possible, draw the structure of any diastereomer of the molecule shown below. 39. What term describes the structural relationship between (E)- and (Z)-2-pentene? A) not isomers B) constitutional isomers C) enantiomers D) diastereomers E) conformers 40. What term describes the structural relationship between cis-1,2-dimethylcyclopentane and trans-1,2-dimethylcyclopentane? A) not isomers B) constitutional isomers C) enantiomers D) diastereomers E) conformers 41. What term describes the structural relationship between cis-1,2-dimethylcyclopentane and trans-1,3-dimethylcyclopentane? A) not isomers B) constitutional isomers C) enantiomers D) diastereomers E) conformers 42. What term describes the structural relationship between (2R,3R,4S)-2,3,4-trichloroheptane and (2S,3S,4R)-2,3,4-trichloroheptane? A) not isomers B) constitutional isomers C) enantiomers D) diastereomers E) conformers 43. Provide a Fischer projection of (2R,3R,4S)-2,3,4-trichloroheptane. 44. Which of the following configurations corresponds to the structure below? A) (4R, 5R) B) (4R, 5S) C) (4S, 5R) D) (4S, 5S) 45. Use the following three structures to answer the questions below. 46. The relationship between I and II is: A) same compound B) enantiomers C) diastereomers D) constitutional isomers 47. The relationship between I and III is: A) same compound B) enantiomers C) diastereomers D) constitutional isomers 48. Which of the structures above are meso structures? A) I B) II C) III D) II & III E) None of the previous ...
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