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Organic Chemistry 4th Edition By Janice Smith Test Bank
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Organic Chemistry 4th Edition By Janice Smith Test Bank
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WITH ANSWERS
Organic Chemistry 4th Edition By Janice Smith Test Bank
Chapter 5: Stereochemistry
| 1. | What is the main carbohydrate in the seeds and roots of plants? |
| A) Starch B) Glucose C) Cellulose D) Glycogen |
| 2. | Which of the following statements about starch and cellulose is true? | |
| A) | Starch and cellulose are not stereoisomers. | |
| B) | In cellulose, the O atom joins two rings using one equatorial and one axial bond. | |
| C) | In starch, the O atom joins two rings using two equatorial bonds. | |
| D) | In cellulose, the O atom joins two rings using two equatorial bonds. | |
| 3. | Which of the following statements about constitutional isomers if not true? | |
| A) | They have different IUPAC names. | |
| B) | They always have the same functional groups. | |
| C) | They have different physical properties. | |
| D) | They have different chemical properties. | |
| 4. | Which of the following statements about stereoisomers is not true? | |
| A) | Stereoisomers have identical IUPAC names except for a prefix like cis or trans. | |
| B) | Stereoisomers differ in configuration. | |
| C) | Stereoisomers always have the same functional groups. | |
| D) | Stereoisomers differ only in their structural formula. | |
| 5. | What is the relationship between the following two compounds?
|
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| A) | Stereoisomers | C) | Identical | |
| B) | Constitutional isomers | D) | Not isomers, different compounds | |
| 6. | What is the relationship between the following two compounds?
|
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| A) | Constitutional isomers | C) | Stereoisomers | |
| B) | Identical | D) | Not isomers, different compounds | |
| 7. | What is the relationship between the following two compounds?
|
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| A) | Constitutional isomers | C) | Stereoisomers | |
| B) | Identical | D) | Not isomers, different compounds | |
| 8. | What is the relationship between the following two compounds?
|
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| A) | Constitutional isomers | C) | Identical | |
| B) | Stereoisomers | D) | Not isomers, different compounds | |
| 9. | Which of the following is the definition of chirality? | |
| A) | The existence of a molecule with a mirror image. | |
| B) | The existence of a molecule with a carbon atom that has four different substituents. | |
| C) | The existence of a molecule that is superimposable on its mirror image. | |
| D) | The existence of a molecule that is not superimposable on its mirror image. | |
| 10. | Which of the following statements is not true? | |
| A) | A molecule that is superimposable on its mirror image is said to achiral. | |
| B) | A molecule that is not superimposable on its mirror image is said to be chiral. | |
| C) | A molecule that is superimposable on its mirror image is said to be chiral. | |
| D) | A carbon atom bonded to four different groups is a stereogenic center. | |
| 11. | Which of the following statements is true? | |
| A) | Enantiomers are mirror images that are not superimposable. | |
| B) | A molecule that is superimposable on its mirror image is chiral. | |
| C) | A chiral molecule usually contains a plane of symmetry. | |
| D) | An achiral molecule does not contain a plane of symmetry. | |
| 12. | Which of the following statements is true? | |
| A) | Achiral molecules usually contain a plane of symmetry. | |
| B) | With one tetrahedral stereogenic center, a molecule may or may not be chiral. | |
| C) | With two or more stereogenic centers, a molecule is always chiral. | |
| D) | Chiral molecules usually contain a plane of symmetry. | |
| 13. | Which of the following is the correct definition for a pair of enantiomers? | |
| A) | A pair of stereoisomers that have a plane of symmetry. | |
| B) | A pair of stereoisomers that are not mirror images of each other. | |
| C) | A pair of stereoisomers that are not superimposable mirror images of each other. | |
| D) | A pair of stereoisomers that are superimposable mirror images of each other. | |
| 14. | Which of the following molecules has a plane of symmetry?
|
| A) I B) II C) III D) IV |
| 15. | Which of the following statements is true? | |
| A) | The presence of a plane of symmetry makes a molecule chiral. | |
| B) | An achiral molecule must have one or more stereogenic centers. | |
| C) | All molecules that have stereogenic centers are chiral. | |
| D) | Stereoisomers that are not superimposable on their mirror image are enantiomers. | |
| 16. | Which of the following molecules are chiral?
I. cis-1,3-Dibromocyclohexane II. 1-Bromo-1-methylcyclohexane III. trans-1-Bromo-3-methylcyclohexane IV. cis-1-Bromo-3-methylcyclohexane |
| A) I, II B) II, III C) I, IV D) III, IV |
| 17. | Which of the following molecules are chiral?
I. 2-Chlorobutane II. 3-Bromopentane III. 1-Bromo-2-methylpropene IV. 2-Bromo-3-methylbutane |
| A) I, II B) I, IV C) II, III D) III, IV |
| 18. | Which of the following molecules are achiral?
|
| A) II, III B) I, II C) I, IV D) III, IV |
| 19. | Which of the following molecules are chiral?
|
| A) II, III B) I, II C) I, IV D) III, IV |
| 20. | How many stereogenic centers are present in ephedrine, a bronchodilator and decongestant?
|
| A) 0 B) 1 C) 2 D) 3 |
| 21. | How many stereogenic centers are present in the following compound?
|
| A) 0 B) 1 C) 2 D) 3 |
| 22. | How many stereogenic centers are present in fructose, a simple sugar?
|
| A) 1 B) 2 C) 3 D) 4 |
| 23. | How many stereogenic centers are present in the following compound?
|
| A) 1 B) 2 C) 3 D) 4 |
| 24. | How many stereogenic centers are present in menthol?
|
| A) 1 B) 2 C) 3 D) 4 |
| 25. | How many stereogenic centers are present in the following compound?
|
| A) 1 B) 2 C) 3 D) 4 |
| 26. | How many stereogenic centers are present in the following molecule?
|
| A) 1 B) 2 C) 4 D) 5 |
| 27. | How many stereoisomers are possible for a molecule with formula CH3CHBrCH(OH)CH3? |
| A) 1 B) 2 C) 3 D) 4 |
| 28. | How many stereoisomers can be drawn for a molecule with formula CH3CH(OH)CH(OH)CH3? |
| A) 1 B) 2 C) 3 D) 4 |
| 29. | What is the total number of possible stereoisomers for the following molecule?
|
| A) 2 B) 4 C) 6 D) 8 |
| 30. | How many isomers can be drawn (constitutional and stereoisomers) for dimethycyclopropane? |
| A) 2 B) 3 C) 4 D) 6 |
| 31. | How many chiral stereoisomers can be drawn for dimethycyclopropane? |
| A) 1 B) 2 C) 3 D) 4 |
| 32. | How many stereogenic centers are present in gabapentin, used clinically to treat seizures and certain types of chronic pain?
|
| A) 0 B) 1 C) 2 D) 3 |
| 33. | How many stereogenic centers are present in the following compound?
|
| A) 0 B) 1 C) 2 D) 3 |
| 34. | Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.
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| A) | III > I > II > IV | C) | III > II > IV > I | |
| B) | I > II > IV > III | D) | III > IV > II > I | |
| 35. | Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.
|
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| A) | I > II > III > IV | C) | II > I > III > IV | |
| B) | II > I > IV > III | D) | I > II > IV > III | |
| 36. | Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.
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| A) | I > III > IV > II | C) | IV > III > I > II | |
| B) | III > IV > I > II | D) | IV > I > III > II | |
| 37. | Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.
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| A) | I > II > IV > III | C) | IV > I > II > III | |
| B) | IV > II > I > III | D) | III > II > I> IV | |
| 38. | Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system.
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| A) | IV > III > I > II | C) | III > IV > I > II | |
| B) | IV > I > III > II | D) | II > I > III > IV | |
| 39. | Which of the following compounds has a plane of symmetry?
|
| A) I and II B) II and III C) II, III and IV D) III and IV |
| 40. | Which of the following structures has a different configuration from the other three?
|
| A) I B) II C) III D) IV |
| 41. | Which of the following structures has a different configuration from the other three?
|
| A) I B) II C) III D) IV |
| 42. | Which of the following structures has the S configuration?
|
| A) Only I B) Only II C) Only I and II D) I, II and III |
| 43. | Which of the following structures has the R configuration?
|
| A) Only I B) Only II C) Only I and II D) I, II and III |
| 44. | Which of the following structures has the R configuration?
|
| A) Only I B) Only II C) Only I and II D) I, II and III |
| 45. | Which of the following is the definition for a pair of diastereomers? | |
| A) | A pair of stereoisomers with stereogenic centers which is not chiral. | |
| B) | A pair of stereoisomers that are superimposable mirror images of each other. | |
| C) | A pair of stereoisomers that are not superimposable mirror images of each other. | |
| D) | A pair of stereoisomers that are not mirror images of each other. | |
| 46. | What is the relationship between the following compounds?
|
| A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical |
| 47. | What is the relationship between the following compounds?
|
| A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical |
| 48. | What is the relationship between the following compounds?
|
| A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical |
| 49. | What is the relationship between the following compounds?
|
| A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical |
| 50. | What is the relationship between the following compounds?
|
| A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical |
| 51. | What is the relationship between the following compounds?
|
| A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical |
| 52. | What is the relationship between the following compounds?
|
| A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical |
| 53. | What is the relationship between the following compounds?
|
| A) Constitutional isomers B) Diastereomers C) Enantiomers D) Identical |
| 54. | Which of the following statements about meso compounds is not true? | |
| A) | A meso compound generally has a plane of symmetry. | |
| B) | A meso compound and its mirror image are identical. | |
| C) | A meso compound is achiral. | |
| D) | A meso compound is chiral. | |
| 55. | Which of the following compounds is a meso compound? | |||
| A) | (2R, 3S)-dichlorobutane | C) | (2R, 3S)-3-chloro-2-butanol | |
| B) | (2R, 3R)-dichlorobutane | D) | (2R, 3R)-3-chloro-2-butanol | |
| 56. | Which of the following compounds are meso?
|
| A) Only I B) Only II C) I and II D) Neither |
| 57. | Which of the following compounds can have a meso stereoisomer?
|
| A) I B) II C) III D) IV |
| 58. | How many stereoisomers of 1,3-dibromocyclopentane exist? |
| A) 1 B) 2 C) 3 D) 4 |
| 59. | Which of the following compounds does not have a plane of symmetry?
|
| A) Only I and II B) Only II C) Only III and IV D) Only I, II and IV |
| 60. | Which of the following cyclic molecules is a meso compound?
|
| A) I B) II C) III D) IV |
| 61. | How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane? |
| A) 3 B) 4 C) 5 D) 6 |
| 62. | A natural product was isolated in the laboratory, and its observed rotation was +10 when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H2O. What is the specific rotation of this compound? |
| A) -10 B) +100 C) +10 D) -100 |
| 63. | A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4. What is the specific rotation of the S enantiomer? |
| A) +50 B) -40 C) +40 D) -50 |
| 64. | How much of the R enantiomer is present in 10 g of a mixture which has an enantiomeric excess of 30% of the S isomer? |
| A) 3.0 g B) 3.5 g C) 6.5 g D) 7.0 g |
| 65. | A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates plane polarized light by +5.6. What is the rotation of a solution containing 0.8 g/mL of the S enantiomer in the same polarimeter. |
| A) +5.6 B) +11.2 C) +2.8 D) +1.4 |
| 66. | What is the percent ee of a mixture that has 70% of one enantiomer and 30% of the other? |
| A) 70 B) 85 C) 40 D) 30 |
| 67. | If a mixture has an ee of 90%, what is the percentage of each enantiomer? |
| A) 65% : 35% B) 55% : 45% C) 80% : 20% D) 95% : 5% |
| 68. | A reaction mixture is three parts of one enantiomer and one part of the other. What is the percent ee of this mixture? |
| A) 75 B) 40 C) 65 D) 50 |
Answer Key
| 1. | A |
| 2. | D |
| 3. | B |
| 4. | D |
| 5. | B |
| 6. | A |
| 7. | B |
| 8. | B |
| 9. | D |
| 10. | C |
| 11. | A |
| 12. | A |
| 13. | C |
| 14. | B |
| 15. | D |
| 16. | D |
| 17. | B |
| 18. | C |
| 19. | A |
| 20. | C |
| 21. | D |
| 22. | C |
| 23. | B |
| 24. | C |
| 25. | B |
| 26. | B |
| 27. | D |
| 28. | C |
| 29. | D |
| 30. | C |
| 31. | B |
| 32. | A |
| 33. | B |
| 34. | D |
| 35. | B |
| 36. | C |
| 37. | C |
| 38. | A |
| 39. | D |
| 40. | A |
| 41. | D |
| 42. | C |
| 43. | B |
| 44. | C |
| 45. | D |
| 46. | B |
| 47. | C |
| 48. | B |
| 49. | D |
| 50. | B |
| 51. | C |
| 52. | A |
| 53. | B |
| 54. | D |
| 55. | A |
| 56. | B |
| 57. | D |
| 58. | C |
| 59. | B |
| 60. | B |
| 61. | D |
| 62. | B |
| 63. | D |
| 64. | B |
| 65. | B |
| 66. | C |
| 67. | D |
| 68. | D |
Chapter 13: Mass Spectrometry and Infrared Spectroscopy
| 1. | In electron impact mass spectrometry (EIMS), what is being detected? | |
| A) | The molecular mass of the compound | |
| B) | The molecular formula of the compound | |
| C) | The mass to charge ratio of any ionic species | |
| D) | The mass to charge ratio of any neutral species | |
| 2. | What type of feature will be observed in the EI mass spectrum of chlorobenzene? | |
| A) | An absorption at 3100 cm1 | |
| B) | A signal at 113. | |
| C) | A signal at 112 and a signal at 114 in a ratio of 3:1 | |
| D) | A signal at 112 and a signal at 114 in a ratio of 1:1 | |
| 3. | You observe a compound that exhibits a mass spectrum with peak at 160 and a peak at 162, both of equal intensity. This compound contains: | |||
| A) | Two chlorine atoms | C) | One bromine atom | |
| B) | One iodine atom | D) | Two bromine atoms | |
| 4. | What type(s) of molecular motion is (are) observed using infrared spectroscopy? | |||
| A) | Stretching and bending | C) | Spin flipping | |
| B) | Rotation and excitation | D) | Fragmentation | |
| 5. | The functional group region of an infrared spectrum is: | |||
| A) | Where the cations appear | C) | Less than 1500 cm1 | |
| B) | Greater than or equal to 1500 cm1 | D) | Greater than or equal to 2500 cm1 | |
| 6. | Stronger bonds will be found where in the infrared spectrum? | |||
| A) | Higher molecular weight | C) | Lower wavenumbers | |
| B) | Lower molecular weight | D) | Higher wavenumbers | |
| 7. | Compared to a CH bond, a CD bond will vibrate where in the infrared spectrum? | |||
| A) | Higher molecular weight | C) | Lower wavenumbers | |
| B) | Lower molecular weight | D) | Higher wavenumbers | |
| 8. | Why does an alkyne carboncarbon triple bond vibrate at a higher wavenumber than an alkene carboncarbon double bond? | |||
| A) | It is stronger. | C) | It has fewer hydrogens. | |
| B) | It is weaker. | D) | It makes a less stable cation. | |
| 9. | Why is the infrared absorption for the stretching motion of internal alkynes rarely observed? | |
| A) | They do not form cations. | |
| B) | They are too strong. | |
| C) | Stretching in internal alkynes does not involve a change in dipole moment. | |
| D) | They do not have hydrogens. | |
| 10. | Consider the three organic compounds drawn below. Which of the following statements is (are) true about the IR spectra of I, II, and III? | |
| A) | I shows strong absorptions at 2950 cm1 and 1700 cm1. | |
| B) | II shows strong absorptions at 2950 cm1 and 2250 cm1. | |
| C) | III shows strong absorptions at 2950 cm1 and 32003600 cm1. | |
| D) | Statements (I shows strong absorptions at 2950 cm1 and 1700 cm1) and (III shows strong absorptions at 2950 cm1 and 32003600 cm1) are true. | |
| 11. | In an IR spectrum, which of the indicated CH bonds exhibits a stretching absorption at the largest wave number?
|
| A) I B) II C) III D) IV |
| 12. | Which of the following statements is (are) accurate about the IR spectrum of compounds I, II, and III below?
|
|
| A) | Compound I shows absorptions at 2950 and 1700 cm1. | |
| B) | Compound II shows absorptions at 32003600 and 1650 cm1. | |
| C) | Compound III shows absorptions at 32003600 and 2950 cm1. | |
| D) | Both (Compound I shows absorptions at 2950 and 1700 cm1) and (Compound II shows absorptions at 32003600 and 1650 cm1) are true. | |
| 13. | Which of the indicated CH bonds absorbs at the lowest wave number in the IR spectrum? |
| A) I B) II C) III D) IV |
| 14. | Which of the following statements is (are) true about the IR spectrum of the compound drawn below? | |
| A) | It shows absorptions at 30003150 cm1 and 1720 cm1. | |
| B) | It shows absorptions at 30002850 cm1 and 2150 cm1. | |
| C) | It shows absorptions at 2250 cm1 and 1650 cm1. | |
| D) | It shows absorptions at 2250 cm1 and 1720 cm1. | |
| E) | Both statements B (It shows absorptions at 30002850 cm1 and 2250 cm1) and D (It shows absorptions at 2250 cm1 and 1720 cm1) are true. | |
| 15. | A compound X shows a molecular ion peak at m/z 72 in its mass spectrum, and a strong peak at ~1715 cm1 in its IR spectrum. Which structures are possible for compound X?
|
| A) I B) II C) III D) I and II |
| 16. | A compound X has a molecular ion peak in its mass spectrum at m/z 136. What information does this tell us about X? | |
| A) | X has a molecular mass of 136. | |
| B) | The molecular formula for X is C8H8O2. | |
| C) | The empirical formula for X is C4H4O. | |
| D) | Both A (X has a molecular mass of 136) and B (The molecular formula for X is C8H8O2) are true. | |
| E) | Statements (X has a molecular mass of 136), (The molecular formula for X is C8H8O2), and (The empirical formula for X is C4H4O) are all true. | |
| 17. | You are given a bottle of an organic liquid and told it must be either cyclohexane or 1-hexene. Which of the following statements is (are) true about these two compounds?
|
|
| A) | The two compounds can be differentiated by their mass spectra because they will have molecular ion peaks at different m/z. | |
| B) | 1-Hexene will show an absorption at 1650 cm1 but cyclohexane will not. | |
| C) | Both cyclohexane and 1-hexene will show CH absorptions at about 2950 cm1. | |
| D) | Statements B (1-Hexene will show an absorption at 1650 cm1 but cyclohexane will not) and C (Both cyclohexane and 1-hexene will show CH absorptions at about 2950 cm1) are both true. | |
| E) | Statements A (The two compounds can be differentiated by their mass spectra because they will have molecular ions at different masses), B (1-Hexene will show an absorption at 1650 cm1 but cyclohexane will not), and (Both cyclohexane and 1- hexene will show CH absorptions at about 2950 cm1) are all true. | |
| 18. | Which of the following statements is (are) true about a compound that has a molecular ion peak in its mass spectrum at mass 104, and shows prominent peaks in its IR spectrum at 32002850 cm1? | |
| A) | The compound has a molecular mass of 104. | |
| B) | The compound contains a C=O group and Csp3-H hybridized bonds. | |
| C) | The compound contains an OH group and Csp3-H hybridized bonds. | |
| D) | Both (The compound has a molecular mass of 104) and (The compound contains a C=O group and Csp3-H hybridized bonds) are true statements. | |
| E) | Both (The compound has a molecular mass of 104) and (The compound contains an OH group and Csp3-H hybridized bonds) are true statements. | |
| 19. | An alkyne CH bond absorbs at higher wave number than an alkene CH bond. What does this tell you about the strength of these two bonds? | |||
| A) | The alkene CH bond is stronger. | C) | The alkene CC bond is stronger. | |
| B) | The alkyne CH bond is stronger. | D) | The alkyne CC bond is stronger. | |
| 20. | Which of the following statements is (are) true about a compound that has a molecular ion peak in its mass spectrum at mass 94, and shows prominent peaks in its IR spectrum at 36003200 and 1600 cm1? | |
| A) | The compound has a molecular mass of 94. | |
| B) | The compound contains a C=O group and Csp3-H hybridized bonds. | |
| C) | The compound contains an OH group and a benzene ring. | |
| D) | Both A (The compound has a molecular mass of 94) and B (The compound contains a C=O group and Csp3-H hybridized bonds) are true statements. | |
| E) | Both A (The compound has a molecular mass of 94) and C (The compound contains an OH group and a benzene ring) are true statements. | |
| 21. | Which of the following statement(s) is (are) true about a compound that has a molecular ion peak in its mass spectrum at mass 69, and shows a prominent peak in its IR spectrum at 2250 cm1? | |
| A) | The compound has a molecular mass of 70. | |
| B) | The compound contains a C=O group. | |
| C) | The compound contains a cyano or alkyne group. | |
| D) | Both (The compound has a molecular mass of 70) and (The compound contains a C=O group) are true statements. | |
| E) | Both (The compound has a molecular mass of 70) and (The compound contains a cyano or alkyne group) are true statements. | |
| 22. | Which of the following statements is (are) true about a compound that has molecular ion peaks in its mass spectrum at mass 170 and 172, and shows prominent peaks in its IR spectrum at 31503000 and 1600 cm1? | |
| A) | The compound is not pure. | |
| B) | The compound contains a halogen. | |
| C) | The compound contains an OH group and Csp3-H hybridized bonds. | |
| D) | Both A (The compound is not pure) and B (The compound contains a halogen) are true statements. | |
| E) | Both A (The compound is not pure) and C (The compound contains an OH group and Csp3-H hybridized bonds) are true statements. | |
| 23. | Which of the following structures is consistent with a compound that displays a molecular ion peak at 103 and infrared signals at 2250 and 1600 cm1?
|
| A) I B) II C) III D) IV |
| 24. | Which of the following structures is consistent with a compound that displays a molecular ion peak at 56 and infrared signals at 2250 and 36003200 cm1?
|
| A) I B) II C) III D) IV |
| 25. | Which of the following structures is consistent with a compound that displays a molecular ion peak at 84 and infrared signals at 30002850 cm1 and no signals between 3000-3300 cm-1?
|
| A) I B) II C) III D) IV |
| 26. | What type of signal(s) would you observe in the mass and (or) infrared spectrum of the following compound?
|
|||
| A) | A signal at 1600 cm1 | C) | A single mass peak at 92 amu | |
| B) | A signal at 3300 cm1 | D) | Two mass peaks at 92 and 94 amu | |
| 27. | What type of signal(s) would you observe in the mass and/or infrared spectrum of the following compound?
|
|||
| A) | A signal at 96 amu | C) | A signal at 1600 cm1 | |
| B) | Two signals at 112 and 114 amu | D) | A signal at 1720 cm1 | |
| 28. | What type of signal(s) would you observe in the mass and (or) infrared spectrum of the following compound?
|
|||
| A) | A signal at 95 amu | C) | Two signals at 95 and 94 amu | |
| B) | A signal at 94 amu | D) | A signal at 36003200 cm1 | |
| 29. | In a typical mass spectrum, a smaller signal is observed at a mass 1 amu higher than the molecular ion peak. Why? | |
| A) | Due to small impurities in the sample | |
| B) | Machine error | |
| C) | Because a small percentage of the compound will have a carbon that is the isotope 13C instead of 12C | |
| D) | Because of fragmentation | |
| 30. | Examine the IR below and classify the compound. |
| A) Alkane B) Carboxylic acid C) Alcohol D) Alkene |
| 31. | Examine the IR below and classify the compound. |
| A) Alcohol B) Aldehyde C) Amine D) Ketone E) Carboxylic acid |
| 32. | Examine the IR below and classify the compound. |
| A) Alcohol B) Arene C) Amine D) Ketone E) Carbocylic acid |
| 33. | Examine the IR below and classify the compound. |
| A) Alcohol B) Aldehyde C) Carboxylic acid D) Ketone |
| 34. | Examine the IR below and classify the compound. |
| A) Alcohol B) Aldehyde C) Amine D) Ketone |
| 35. | 13C NMR is a technique in which the total number of signals represents the number of unique carbon atoms in a molecule. Propose a structure that is consistent with the following data.
a) The IR includes peaks at 1603 and 1495 cm-1. b) The 13C NMR has a total of 7 signals. c) The compound has one acidic proton.
|
| A) I B) II C) III D) IV |
| 36. | The base peak in a mass spectrum corresponds to the most stable fragment. Propose a structure for a compound that is consistent with the following data.
a) The molecular ion peak has m/z = 116 b) The base peak is at m/z = 59. c) The compound is composed of C, H and O atoms. d) The IR spectrum shows a strong absorbance at 3257 cm-1.
|
| A) I B) II C) III D) IV |
| 37. | An IR spectrum has the following potentially important absorptions: 3091, 3067, 2963, 2921, 2252, 1603, 1499, 1455, 1416, 1078, 1031, 941, 735, and 696 cm-1. Indicate which structure corresponds to the IR data.
|
| A) I B) II C) III D) IV |
| 38. | When the phenol shown below is treated with KOH, it forms a product whose IR spectrum does not show an absorption in the 3200-3600 cm-1 region. Propose a structure for the product.
|
| A) I B) II C) III D) IV |
| 39. | Which of the following information is primarily obtained from an IR spectrum? | |
| A) | Conjugated p system present in a compound. | |
| B) | Functional groups present in a compound. | |
| C) | Molecular weight of a compound. | |
| D) | The carbon and hydrogen framework of a compound. | |
| 40. | Which of the following compounds will have the lowest wavenumber for carbonyl absorption?
|
| A) I B) II C) III D) IV |
| 41. | Which of the following p bonds is IR inactive?
|
| A) I B) II C) III D) IV |
| 42. | Which of the following statements about the base peak of a mass spectrum is always true? | |
| A) | The base peak corresponds to the molecular ion. | |
| B) | The base peak corresponds to the most abundant ion. | |
| C) | The base peak corresponds to the lowest m/z. | |
| D) | None of the above. | |
Answer Key
| 1. | C |
| 2. | C |
| 3. | C |
| 4. | A |
| 5. | B |
| 6. | D |
| 7. | C |
| 8. | A |
| 9. | C |
| 10. | D |
| 11. | A |
| 12. | D |
| 13. | C |
| 14. | E |
| 15. | A |
