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CHEM 2425. Review for Final Exam (all chapters). Central
Multiple Choice Identify the choice that best completes the statement or answers the question.
____ 1. Which of the following is/are primary (1°) alcohols?
a. only 1 b. only 3 c. only 1 and 3 d. only 2 , 3 , and 4
____ 2. What is the IUPAC name of the following compound?
a. ( E)- 2-methyl-3-penten-2-ol b. (Z)-2-methyl-3-penten-2-ol c. ( E)- 4-methyl-2-penten-4-ol d. (Z)-2-methyl-4-penten-2-ol
____ 3. Which of the following has the highest boiling point? a. pentane b. methyl propyl ether c. diethyl ether d. 1-butanol
____ 4. What is the major organic product obtained from the following reaction?
a. (^) 1 b. 2 c. 3 d. (^) 4
____ 5. What is the best choice of reagent to achieve the following transformation?
a. HCl b. Cl (^) 2, light c. SOCl 2 , pyridine d. HOCl, H2O
____ 6. What is the correct assignment of the names of the following ethers?
a. 1 = oxirane; 2 = oxetane; 3 = oxane b. 1 = oxirane; 2 = oxitane; 3 = oxane c. 1 = oxane; 2 = dioxane; 3 = oxetane d. 1 = oxirane; 2 = oxolane; 3 = oxane
____ 7. Which of the following are thiols?
a. only 1 b. only 2 c. only 3 d. both 2 and 3
____ 12. What is the best choice of reagent(s) to perform the following transformation?
a. CH3MgBr; followed by H 3 O+ b. H2O, NaOH c. LiAlH 4 followed by H3O+ d. KMnO
____ 13. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. (^) 4
____ 14. What is the major organic product obtained from the following reaction?
a. 1
b. 2 c. 3 d. (^) 4
____ 15. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
____ 16. What would be the best choice of reagent(s) to perform the following transformation?
a. H2O 2 b. NaIO 4 c. H2O, NaOH d. H2SO 4
____ 17. Which feature in the 1 H NMR spectrum provides information about the number of types of different protons in a compound? a. number of signals b. integral c. splitting d. chemical shift
____ 18. What is the splitting of the signal in the 1 H NMR spectrum for the methyl protons of 1-bromo-2-methylpropane? a. singlet b. doublet c. triplet d. nonet
____ 19. What is the appearance of the signal corresponding to the CH 2 protons in the 1 H NMR spectrum of ethyl methyl ether, CH 3 CH 2 OCH3? a. a doublet b. a triplet
a. ( E )-4-methyl-4-hepten-3-one b. (Z)-4-methyl-4-hepten-3-one c. ( E )-4-methyl-3-hepten-5-one d. (Z)-4-methyl-3-hepten-5-one
____ 27. What is the major organic product obtained from the following reaction?
a. 2-phenyl-2-butanol b. 3-phenyl-2-butanol c. 3-phenylbutanone d. propiophenone, PhCOCH 2 CH 3
____ 28. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound?
a. only 1 and 2 b. only 3 and 4 c. only 2 and 3 d. only 1 , 2 and 3
____ 29. What is the major organic product obtained from the following sequence of reactions?
a. (^) 1 b. 2 c. 3 d. (^) 4
____ 30. What is the major organic product obtained from the following reaction?
a. (^) 1 b. 2 c. 3 d. (^) 4
____ 31. What is the major organic product obtained from the following reaction?
a. 2-methyl-2-heptene b. 3-ethyl-2-pentene c. ( Z ) 2-methyl-3-heptene d. ( E ) 2-methyl-3-heptene
____ 32. What is the major organic product obtained from the following reaction?
a. 1 b. (^) 2 c. 3 d. 4
____ 36. What is the major organic product obtained from the following sequence of reactions?
a. 1 b. (^) 2 c. 3 d. 4
____ 37. Which of the following statements is not true? a. The reaction of a ketone with methanol in the presence of acid to give a acetal proceeds via a resonance stabilized cation b. Protonation of a ketone increases its electrophilicity c. The conversion of a hemiacetal to an acetal under acidic conditions proceeds via an SN 1 mechanism d. The conversion of a hemiacetal to an acetal is catalyzed by both acid and base
____ 38. What is the reactivity of Br 2 in the acid-catalyzed bromination of acetophenone? a. acid
b. base c. nucleophile d. electrophile
____ 39. What is the major organic product obtained from the following reaction?
a. (^) 1 b. 2 c. 3 d. (^) 4
____ 40. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. (^) 4
____ 41. What is the best choice of reagent(s) to perform the following transformation?
____ 46. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. 3 d. 4
____ 49. What is the major organic product obtained from the following reaction?
a. (^) 1 b. 2 c. 3 d. (^) 4
____ 50. What is the best choice of reagent(s) to achieve the following transformation?
a. H2O b. NaOH, H2O c. 1. LiAlH4; 2. H 3 O+ d. H2SO 4
____ 51. What is the major organic product of the following sequence of reactions?
____ 54. What is the major organic product obtained from the following reaction?
d. 4
____ 56. What is the correct order of exothermicity for hydrogenation of the following hexadienes upon treatment with H2/Pd (more exothermic > less exothermic)?
a. 1 > 2 > 3 b. 3 > 1 > 2 c. 2 > 1 > 3 d. 3 > 2 > 1
____ 57. Which of the following arrangements of p atomic orbitals gives the highest energy π-antibonding molecular orbital of 1,3-butadiene?
a. 1 b. (^) 2 c. 3 d. (^) 4
____ 58. What is (are) the major organic product(s) formed in the following reaction?
a. only 1 b. only 2 c. only 1 and 3 d. only 2 and 4
____ 59. What are the units of absorbance, A , in ultraviolet-visible spectroscopy? a. (^) J⋅mol−^1 b. (^) nm⋅mol−^1 c. (^) J⋅mol−^1 ⋅M−^1 d. none, A is a dimensionless quantity
____ 60. What are the units of ε in ultraviolet-visible spectroscopy?
a. (^) M−^1 ⋅cm−^1
____ 66. What is the major organic product obtained from the following reaction?
- a.
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- a. ____ 47. What is the major organic product obtained from the following reaction?
- b.
- c.
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- a.
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- a. ____ 55. What is the major organic product obtained from the following reaction?
- b.
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a. 1 b. (^) 2 c. 3 d. (^) 4
____ 68. What is the major organic product obtained from the following reaction?
a. 1 b. 2 c. (^) 3 d. 4
____ 69. What is the role of AlCl 3 in Friedel Crafts acylations using acid chlorides? a. Lewis acid b. electrophile c. base d. nucleophile
____ 70. Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions? a. CH3, OCH3, COCH 3 b. Cl, CN, NO 2 c. Cl, NH2, CH 3 d. CH3, NH2, OCH 3
____ 71. Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions? a. Cl, CN, NO 2 b. Cl, NH2, CH 3 c. CH3, OCH3, COCH 3 d. CH3, NH2, OCH 3
____ 72. Which of the following reactions or sequences will provide 1-propylbenzene as the major product? a. treatment of benzene with isopropyl alcohol and HF b. treatment of benzene with propanoyl chloride and AlCl 3 ; followed by reaction with Zn(Hg) and HCl c. treatment of benzene with 1-chloropropane and AlCl (^3) d. treatment of benzene with 1-propene and HF
