Folder test bank is orgo chapter 5

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Alkenes contain the C=C functional group which can be prepared by 1,2-elimination reactions such as:
• dehydration of alcohols (- H2O) or
• dehydrohalogenation of alkyl halides (- HX).
Zaitsev's rule indicates that the preferred product is the more highly substituted, and therefore more stable alkene. But the rule is not always obeyed and the anti-Zaitsev (or Hofmann) product can dominat

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Folder test bank is orgo chapter 5

  1. 1. Chapter 5 Structure and Preparation of Alkenes - Elimination Reactions • .
  2. 2. • 1. Carbon-carbon double bonds do not freely rotate like carbon-carbon single bonds. Why? • A. The double bond is much stronger and thus more difficult to rotate. • B. Overlap of the two 2p orbitals of the bond would be lost. • C. The shorter bond length of the double bond makes it more difficult for the attached groups to pass each other. • D. Overlap of the sp2 orbitals of the carbon-carbon bond would be lost.
  3. 3. • 2. What is the IUPAC name of the following compound? • • • • A. B. C. D. 2,5-dimethyl-1-hexene 1,4-dimethyl-1-hexene 2,5-dimethyl-2-hexene 2,5-dimethyl-5-hexene
  4. 4. • 3. What is the IUPAC name of the following compound? • • • • A. B. C. D. 2-methyl-3-propyl-2-pentene 3-ethyl-2-methyl-2-hexene 4-ethyl-methyl-4-hexene 4-methyl-3-propyl-3-pentene
  5. 5. • 4. What is the IUPAC name of the following compound? • • • • A. B. C. D. 3-ethyl-8-methyl-3-nonene 7-ethyl-2-methyl-6-nonene 1,1-diethyl-6-methyl-3-heptene 3-ethyl-7-isopropyl-3-octene
  6. 6. 5. How many isomeric alkenes of formula C4H8, including stereoisomers, are possible? • • • • • A. B. C. D. two three four five
  7. 7. 6. How many isomeric alkenes of formula C5H10, including stereoisomers, are possible? • • • • A. B. C. D. three four five six
  8. 8. • 7. What is the IUPAC name of the following compound? • • • • A. B. C. D. 3-bromo-2-methylcyclohexene 1-bromo-2-methyl-2-cyclohexene 6-bromo-1-methylcyclohexene 2-bromo-1-methylcyclohexene
  9. 9. • 8. What is the IUPAC name of the following compound? • • • • A. B. C. D. 3-ethyl-propyl-1-heptene ethyl-3-vinyloctane 4,6-diethyl-1-octene 3,5-diethyl-1-octene
  10. 10. • 9. Which of the following alkenes exhibit E-Z isomerism? • • • • A. B. C. D. I and II I and III II and IV I, II, and III
  11. 11. • 10. Which of the following alkenes exhibit E-Z isomerism? I. 1-chloropropene II. 2-chloropropene III. 3chloropropene • • • • A. B. C. D. only I I and II II and III I and III
  12. 12. • 11. What is the IUPAC name of the following compound? • • • • A. B. C. D. (E)-3-bromo-1-fluoro-2-methylpropene (Z)-3-bromo-1-fluoro-2-methylpropene (E)-1-bromo-3-fluoro-2-methylpropene (Z)-1-bromo-3-fluoro-2-methylpropene
  13. 13. • 12. Which of the following C6H12 isomers has the highest heat of combustion? • • • • A. B. C. D. 1-hexene trans-3-hexene cis-3-hexene 2-methyl-2-pentene
  14. 14. • 13. Identify the major organic product expected from the acid-catalyzed dehydration of 2-methyl-2-pentanol. • • • • A. B. C. D. 2-methyl-1-pentene 2-methyl-2-pentene 3-methyl-1-pentene cis-3-methyl-2-pentene
  15. 15. 14. Which alcohol below would undergo acid-catalyzed dehydration most readily? • • • • • A. B. C. D. A B C D
  16. 16. • 15. What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2-methyl-2-propanol? • A. Protonation of the alcohol to form an oxonium ion. • B. Loss of water from the oxonium ion to form a carbocation. • C. Loss of a b-hydrogen from the carbocation to form an alkene. • D. The simultaneous loss of a b-hydrogen and water from the oxonium ion.
  17. 17. • 16. Which of the following carbocations is(are) likely to undergo a rearrangement? • • • • A. B. C. D. only I I and III II and III I, II, and III
  18. 18. • 17. Predict the major product of the following reaction. • • • • A. B. C. D. A B C D

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