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Exam 2

by: Nadelyn Pichardo
Nadelyn Pichardo
SUNY Oswego

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About this Document

Study sheet made for exam 2. Covers all of the subjects that were tested during this exam.
organic chemistry
Fehmi Damkaci (P)
Study Guide
Chemistry, organic, Chemistry
50 ?




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This 11 page Study Guide was uploaded by Nadelyn Pichardo on Friday July 15, 2016. The Study Guide belongs to CHE 331 at State University of New York at Oswego taught by Fehmi Damkaci (P) in Fall 2015. Since its upload, it has received 12 views. For similar materials see organic chemistry in Chemistry at State University of New York at Oswego.

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Date Created: 07/15/16
1. Give a complete IUPAC name for each compound below, including designation of  stereochemistry, including designation of stereochemistry if it is specifically shown. a) b)  2. Describe the difference between structure A and structure B using appropriate  terminology. Predict which would be more stable. 3. Which functional group is present in the following molecule? a. d. b. e. c. f. 4. What type of alcohol is this? a. 5. What is the major product of the following reaction? 8. ? 6. 7. 11. 14. 10. 12. 13. 15. 16. A 17. 18. B 19. C 20. D 21. E 22. The spatial orientation of the atoms of a molecule is called it’s what? a. Constitution c. Handedness b. Configuration d. Composition 23. An object that has no element of symmetry is called what? a. Tetrahedral c. Symmetric b. Achiral d. Asymmetric 24. Stereoisomers differ from each other in what respect? a. Composition c. Configuration b. Constitution d. Steric hindrance 25. Which of the following must be true for an optically active compound? a. The molecular configuration is achiral b. The molecular configuration is chiral c. The compound is racemic mixture of enantiomers d. The molecular configuration must have two or more stereogenic centers 26. Enantiomers are? a. Stereoisomers having non­identical mirror image configurations b. Stereoisomers that do not have non­identical mirror image configurations c. Stereoisomers having a mirror plane of symmetry d. Achiral stereoisomers e. 27. Which conformation if cyclohexane has a C  axis of symmetry? 3 a. Boat c. Chair b. Twist boat d. Envelop 28. The following compound has how many stereogenic centers? 29. a. 0 c. 2 b. 1 d. 3 30. Hydration, by oxymercuation, of 3­methyl­1­butene gives 3­methyl­2­butanol. What is the observed rotation of this product, using a 20% solution in ethanol in a 1dm  polarimeter cell? Assume the specific rotation of the pure (S)­enantiomer to be +16º a. +3.2 c. 180 (+ or ­) b. ­3.2 d. 0 31. Which of the following is (R)­3­hexanol? 32. 33. Which two Fischer formulas represent a pair of enantiomers?  34. 35. Consider the Fischer projection formula for (S)­2­chlorobutane. Which of the following  changes does not convert this structure to the (R)­enantiomer?  a. rotation 180º in the plane of  c. exchanging the two vertical  the paper (or screen) substituents (i.e. top and  b. flipping the structure over (a  bottom) 180º rotation out of the  d. exchanging the two  plane) horizontal substituents (i.e.  right and left) 36. Which of the following represents (E)­3, 6­dichloro­6­methyl­3­heptene?  37. 38. Designate the CIP priority order of the following C H ­ gr5up11 (Lowest < Highest  priority order) I CH (3H ) 2 4 II (CH ) C3 3–   I2I C H CH(3H 7–   IV (3H ) CHCH CH –3 2 2 2 a.   b. I < II < III < IV d. I < IV < II < III c. IV < III < II < I e. III < II < IV < I 39. Which of the following compounds has two stereogenic centers (asymmetric carbons)? 40. 41. Which of the following compounds is (S)­4­chloro­1­methylcyclohexene?  42. 43. Which two of the following compounds represents a pair of enantiomers?  44. 45. Which of the following is properly classified as a meso compound? 46. 47. When HOBr adds to 4­methylcyclopentene, how many new stereogenic centers are  formed?  a. 1 c. 3 b. 2 d. 4 48. Which of the following isomeric dienes is chiral?  a. 2,3­pentadiene c.  2­methyl­1,3­butadiene b. 3­methyl­1,2­butadiene  d. none, all are achiral 49. Which two of the following compounds are diastereomers? 50. 51. Two equivalents of bromine add to one equivalent of 1, 7­octadiene.   How many stereoisomeric tetrabromides will be formed?  a. 1. c. 3 b. 2 d. 4 52. Two equivalents of OsO 4hydroxylate one equivalent of 1, 5­cyclooctadiene.   How many stereoisomeric cyclooctane­1, 2, 5, 6­tetraols will be formed?  a. 1 c. 3 b. 2 d. 4 53. The optically active bromohydrin (1R, 2R)­2­bromocyclohexanol reacts with base to  produce cyclohexene oxide (C H 6)10 c. the observed optical rotation  b.  the observed optical rotation  does not change sign    Whichchanges sign wing statements is true? d. the product is achiral 54. Which of the following sugars has the configuration (2S, 3R, 4R)? 55. 56.  How many stereogenic carbon centers are there in morphine, structure shown below? 57. 58. Pure (S)­2­butanol has a specific rotation of +13.52 degrees.  You have made and purified a sample that has a calculated specific rotation of +6.76  degrees.  What can you conclude about this sample? a. the sample has completely  c. 50% of the sample has  racemized racemized b. 50% the sample has  d. 75% of the sample has  rearranged into a meso  racemized isomer 59. How many stereoisomers of (CH ) CH3 2CHCH CH (OH) C22Br are possible? 60.  If two isomers have been classified correctly as epimers, they may also be called...? a. Diastereomers c. tautomers b. enantiomers  d. conformers 61. The drawing shows that cis­1, 2­dichlorocyclohexane is chiral. Efforts to resolve this compound fail. Why?  62. a.  The cis and Trans isomers rapidly interconvert. b.  The compound is actually a meso structure. c. The chair conformers rapidly interconvert producing a racemic mixture. d. Methods for resolving alkyl chlorides are not available. 63. Which of the following statements must be true for two pure chiral isomers? a. they must be enantiomers c. they must be stereoisomers b.  they must be diastereomers d. they must be optically active 64. Which two of the following compounds are identical? 65. The structural formula on the right is that of camphor. Which of the following statements  is correct?  66. a. This compound has two stereogenic centers and exists as a pair of enantiomers. b.  This compound is achiral. c. This compound has three stereogenic centers and exists as a pair of enantiomers  and a meso isomer. d. This compound does not have an enantiomer 67. Which of the following statements is true for a pair of diastereomers? a.  They will have identical physiological properties.  b.  They will have specific rotations of opposite sign. c. they will have identical chemical properties (e.g. reactivity) d.  They will have different physical properties. 68. Which of the following descriptive terms would never be applied to a pair of  stereoisomers? a.  Enantiomers c. Diastereomers b.  Tautomers d. Epimers 69. What kind of reagent would be needed to resolve a racemic amine, such as 2­ aminobutane? a. The pure optically active amine to serve as a template for crystallization. b. An achiral carboxylic acid to give a racemic mixture of amine salts. c.  An enantiomerically pure chiral carboxylic acid to give a diastereomeric mixture  of amine salts. d. A racemic chiral carboxylic acid to give a complete mixture of isomeric amine  salts. 70. What common symmetry elements if any are found in the stable chair conformer of trans­ 1, 4­dichlorocyclohexane? a. A single mirror plane and a C  r2tational axis. b.  A C  3otational axis but no mirror plane. c.  Two orthogonal mirror planes and a C  ro2ational axis. d. A single C  2otational axis but no mirror plane. 71. What common symmetry elements if any are found in the stable chair conformer of trans­ 1, 2­dichlorocyclohexane? a. A single mirror plane and a C  rot2tional axis. b. A single mirror plane and a C  rot3tional axis. c.  Two orthogonal mirror planes and a C  rotat2onal axis. d. A single C  r2tational axis but no mirror plane. 72. Reaction of 3­methyl­1, 4­cycloheptadiene with excess perbenzoic acid (C H CO H)  6 5 3 forms a diepoxide product. How many stereoisomers, counting enantiomers, are expected from this reaction? a. 4 (two pairs of enantiomers) b. 4 (two meso compounds and a pair of enantiomers) c.  5 (two pairs of enantiomers and a meso compound) d.  6 (two pairs of enantiomers and two meso compounds) 73.  The antimalarial alkaloid quinine, C H N20 24is2o2tically active.    An ethanol solution of 8g quinine in 100mL displays a rotation of ­13.6º in a 1dm  polarimeter tube.   What is the specific rotation of quinine? a. ­85º c. ­43º b.  ­170º d. ­26º 74. A C H7O14ptically active alcohol is oxidized by Jones' reagent to an optically inactive  (achiral) ketone. Which of the following compounds meets these facts? 75. 76. Which of the following compounds has a prochiral methylene group (i.e. the hydrogen  atoms are diastereotopic)? a. propane , CH CH CH c. 2­methylpropene ,  3 2 3 b. cyclopropane , (CH ) 2 3 CH =2(CH ) 3 2 d. ethanol , CH CH3OH 2 77. The thermal electrocyclic closure of (2E, 4Z, 6E)­2, 4, 6­octatriene gives which of the  following? a. cis­5,6­dimethyl­1,3­cyclohexadiene b. trans­5,6­dimethyl­1,3­cyclohexadiene c. cis­3,6­dimethyl­1,4­cyclohexadiene d. cis­3,6­dimethyl­1,4­cyclohexadiene 78. The Cope rearrangement, [3, 3]­sigmatropic shift, of meso­3, 4­dimethyl­1, 5­hexadiene  gives which of the following? a. 1,7­octadiene c. (2E,6Z)­2,6­octadiene b. (2Z,6Z)­2,6­octadiene d. (2E,6E)­2,6­octadiene 79. Which is the expected product from the following Diels­Alder reaction? 80. Which of the following structures represents a chiral compound? 81. 82. Which of the following compounds has an S configuration? 83. How should the following structure of polypropylene be classified? 84. Which of the following C H 8i16mers is thermodynamically most stable? 85. Which of the following statements is not an essential feature of an optically active  compound? a. The molecules of an optically active compound will be dissymmetric or  asymmetric. b. The molecules of an optically active molecule must have at least one stereogenic  site. c. An optically active compound's molecular configuration will not be identical with its mirror image. d.  An optically active compound will have at least one stereoisomer. 86. Which of the following statements is not correct? a.  A pair of enantiomeric compounds will have the same melting point. b. A pair of enantiomeric compounds will have the same solubility in ethanol. c. A pair of enantiomeric compounds will have exactly the same functional groups. d. A pair of enantiomeric compounds will have identical optical rotations. 87. Which of the structures on the right, if any, represents syndiotactic polyacrylonitrile?   88. 89. How many stereoisomers having this constitution are possible? 90.   a. 2 c. 6 b. 4 d. 8 91.  Which of the following is (2R, 3S)­2, 3­pentanediol? 92. 1. a) (3S,4E)­2,3­dimethyl­1,4­hexadiene b) 6,6­dimethyl­1,4­cyclooctadiene 2. The two structures are conformations of 1,3­butadiene, which differ only by rotation around  the C2­C3 single bond. The trans­like conformation should be more stable. (Called s­trans,  where s­ means a single bond conformation) 6. B 7.D 8. C 9B 10A 11C 12D 13D 14B 15B 16A 17C 18C 19D 20A 21C 22A 23C 24A 25D 26C 27B 28D 29C 30B 31C 32C 33A 34C 35D 36B 37A 38D 39B 40C 41A 42D 43B 44B 45C 46D 47A 48C 49A 50D 51B 52A 53C 54B 55D 56C 57D 58B


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