ORGANIC CHEMISTRY CHEM 2210 SECOND REVIEW EXAM FALL *A*
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1 ORGANI EMISTRY EM 2210 SEOND REVIEW EXAM ALL *A* 1. What is the IUPA name of the compound shown? O A. cis-1-chloro-4-cyclohexanol B. cis-4-chlorocyclohexanol. trans-1-chloro-4-cyclohexanol trans-4-chlorocyclohexanol 2. Which of the following is NOT a product of the reaction shown? 3 2 ( 3 ) 2 2 Light A. 2 2 ( 3 ) 2 B. 3 2 ( 3 ) 2. 3 ( 3 ) Give the IUPA name of : Br O 3 3 A. (2R,3S,4S)-3-bromo-3,4-dichloro-2-pentanol B. (1R,2R,3R)-2-bromo-2,3-dichloro-1,3-dimethyl-propanol. (1R,2S,3R)-2-bromo-1,2-dichloro-1,3-dimethyl-3-propanol (2R,3S,4R)-3-bromo-3,4-dichloro-2-pentanol
2 4. Which of the following compounds is chiral? A. B.. 5. Which of the following compounds reacts the ASTEST as a substrate in an S N 1 reaction? A. ( 6 5 ) 3 O B. ( 6 5 ) 3 I. ( 6 5 ) 3 S ( 6 5 ) 3 6. Which of the following statements is true about the following reaction? 2 2 O O 3 O - S N 2 A. The product will have R configuration. B. The product will not have a stereocenter.. The product will have S configuration. The reaction will happen with racemization. 7. Which of the following is the most stable conformation of cis-1,3-dimethylcyclohexane? A. B
3 8. Which of these cycloalkanes shows cis-trans isomerism? A. B.. 9. Which of the following is (2R,3R)-2,3-diaminobutane? N 2 2 N N 2 A. B. N 2 2 N. 2 N N N Which of the following is the most stable carbocation having the molecular formula 4 9 +? 2 A. 3 3 B Which of these structures is NOT the product of the following reaction? 3 Br O - 3 O A. B O O Which of the following sets of reagents and conditions will complete the following reaction? +?? A. 2, Ni or Pt catalyst B. aqueous, heat. 3, light 2, light
4 13. Which of the following compounds has a meso stereoisomer? O A O B onsider the following molecule: ( 3 ) 2 Br If Br and 3 group switch their places, what would the relationship between the new molecule and the one above be? A. onstitutional isomers B. Same compound. Enantiomers Diastereomers 15. Which of the following structures is the LEAST stable? 2 3 A. B
5 16. Which of the following conditions are suitable for the synthesis of 2,2-dimethylbutane? I. 3 2 Br with Li, then ui, then ( 3 ) 3 -Br II. ( 3 ) 3 2 -Br with Li, then ui, then 3 Br III. ( 3 ) 3 -Br with Li, then ui, then 3 2 Br A. I and II only B. I and III only. II and III only II only 17. A particular sample of compound Z containing a mixture of the R and S enantiomers has a specific rotation of degrees. The specific rotation of the pure S enantiomer of compound Z is 50.0 degrees. What is the % optical purity of this sample, and how much of the S enantiomer is present? A. 70%, 30% S B. 30%, 35% S. 30%, 65% S 35%, 70% S 18. Which of the following is a feature of an E2 reaction? A. The rate of reaction depends on the concentration of base. B. It is a two step process.. It goes via a reactive intermediate. It is faster in more polar solvents. 19. What is the name of the compound shown? A. 2-ethyl-4,5-dimethylhexane B. 5-ethyl-2,3-dimethylhexane. 3,5,6-trimethylheptane 2,3,5-trimethylheptane
6 20. What will be the major product(s) of the following reaction? 3 32O + I >? 25 I 3 I 3 3 I II III A. I only B. II only. III only Equal amounts of I and II 21. The reaction of 2-methylbutane with chlorine in the presence of UV light will yield compounds (including stereoisomers) of molecular formula 5 11, of which are optically active. The total number of fractions that can be isolated by distillation is. A. 4, 2, 4 B. 6, 4, 4. 6, 4, 2 4, 4, What is the relationship between the structures shown? A. Enantiomers B. Diastereomers. Same compound Structural isomers 23. Molecule A is the enantiomer of molecule B. Molecule B is a stereoisomer of molecule but NOT its mirror image. What is the relationship between A and? A. Same compound B. Enantiomers. Diastereomers onstitutional isomers
7 24. Which of the following statements about the relative stabilities of the structures shown is TRUE? 3 3 I II 3 3 A. II has more steric strain. B. II has more torsional strain.. I has more steric strain. I has more torsional strain. 25. While studying the reaction [RBr] [ 3 ONa] Relative Rate below, a chemist obtained the rate data shown at right. What is the mechanism of this reaction? Br + 3 ONa -----> O 3 + NaBr A. SN1 B. SN2. E1 E2
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