Second Review Exam -- Organic Chemistry, CHEM November *A*
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1 Second Review Exam -- Organic Chemistry, CEM November *A* 1. What are the reagents and conditions necessary to complete the following reaction?? C 3 C 3 C 3 C 2 + Zn, B. 2, Ni (catalyst) 2, light, light 2. Which of these choices correctly describes the positions of the isopropyl and hydroxyl groups in the most stable conformation of cis-4-isopropylcyclohexanol: isopropyl equatorial, O equatorial B. isopropyl axial, O axial isopropyl equatorial, O axial isopropyl axial, O equatorial 3. Which of the following alkanes has the lowest boiling point? B. 4. Which of the following statements is NOT true? Any molecule with a stereocenter must have a stereoisomer. B. Every meso compound is achiral. Any molecule containing tetrahedral stereocenters must be chiral. Every chiral compound has an enantiomer. 5. What is the percentage of R enantiomer in a sample that has the enantiomeric excess (optical purity) of 60% of the S enantiomer? 20% B. 30% 40% 60%
2 6. What is the relationship between the following structures? C 3 O 3 C O 3 C O O C 3 Same compound B. Enantiomers Diastereomers Structural isomers 7. Which of he following is the slowest-reacting leaving group? O B. CF 3 SO 3 2 O 8. Which of the following statements is NOT true about a reaction represented by the following energy reaction coordinate diagram: energy reaction coordinate This diagram can represent any S N 2 reaction. B. This diagram can represent any E2 reaction. This diagram can represent any exothermic reaction. This diagram can represent any endothermic reaction 9. Which of the following solvents will accelerate S N 2 reactions between methyl iodide and KO the most? DMSO B. water petroleum ether acetic acid
3 10. Which of the following represents a gauche conformation? C 2 5 C 2 5 C 2 5 C2 5 B. C 2 5 C 2 5 C 2 5 C What is the UPAC name of the compound shown? O cis-1-chloro-2-hexanol B. cis-1-chloro-2-cyclohexanol trans-2-chlorocyclohexanol cis-2-chlorocyclohexanol 12. Which of the following is NOT a product of the reaction shown? + 2 hυ B.
4 13. What is the UPAC name of the compound shown? O C 3 C 3 (2S,3R,4R)-3,4-dichloro-3-bromo-pentanol B. (2R,3S,4R)-3-bromo-3,4-dichloro-2-pentanol (1R,2S,3R)-3-bromo-3,4-dichloro-1-methyl-pentanol (2R,3S,4S)-3-bromo-3,4-dichloro-2-pentanol 14. Which of the following is a meso compound? B. 15. What is the relationship between the following two compounds? Structural isomers B. Not related Geometric isomers Same 16. Which of the following compounds reacts FASTEST in S N 1 reactions? (C 3 ) 3 CO B. (C 3 ) 3 C (C 3 ) 3 CN 2 (C 3 ) 3 C
5 17. Which of the following statements is TRUE about the reaction shown? O C OC 3 O - The product is achiral. B. O- is acting as a base. The reaction happens with racemization. The reaction happens with retention of configuration. 18. What is the UPAC name of the compound shown below? C 3 C(C 3 ) 3 C2C3 4-Ethyl-2,2-dimethylpentane B. 2,2,4-Trimethylhexane 2-Ethyl-4,4-dimethylpentane 1-tert-butyl-2-ethylpropane 19. Which of these molecules does NOT have a plane of symmetry? F F O C3C2 C C3 C3 O O C3 B.
6 20. What is the relationship between the structures shown? O O O C C C C C 2 C 3 C 3 C 3 O C 2 C 3 Same compound B. Enantiomers Diastereomers Structural isomers 21. Which of these statements is not true for a meso compound? The specific rotation is 0. B. There is at least one plane of symmetry. A single molecule is superposable on its mirror image. The stereochemical labels, R and S, must be the same for all stereocenters. 22. What is the major organic product of the following reaction? C3C2O? 25, second order C3 OC2C3 3 C C3 B. OC2C3 3 C C3
7 23. Which of the following compounds would undergo an S n 2 reaction most RAPDLY? 1-chloropentane B. 2-chloro-2-methylbutane 2-chloropentane Neopentyl chloride 24. n the substitution reaction of C 3 with O-, doubling the concentration of both the substrate and the nucleophile leads to No change B. Doubling of the rate Tripling of the rate Quadrupling of the rate 25. What is the major product of the following reaction? + C3S ----->? B. SC3 SC3
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