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Question 1

Question 1. Name the alkene below according to the IUPAC system. A) 2-bromo-5-heptane B) 6-bromo-2-heptene C) 2-bromo-5-heptene D) 5-bromo-2-heptene. Question 5. Which alkene can have cis/trans stereoisomers? A) B) C) D). Question 6.

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Question 1

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  1. Question 1 • Name the alkene below according to the IUPAC system. • A)2-bromo-5-heptane • B)6-bromo-2-heptene • C)2-bromo-5-heptene • D)5-bromo-2-heptene

  2. Question 5 • Which alkene can have cis/trans stereoisomers? • A) B) • C) D)

  3. Question 6 • Of the compounds with the formula C3H5Cl, which one has cis/trans isomers? • A)1-chloropropene • B)2-chloropropene • C)3-chloropropene • D)all of them

  4. Question 22 • Which one of the following groups has the highest rank when precedence is assigned • according to the Cahn-Ingold-Prelog system? • A)-CH2Cl • B)-CH=O • C)-C(CH3)3 • D)CH2NH2

  5. Question 7 • Assign the configuration of the alkenes below as Z or E, respectively. • A) E,E • B) E,Z • C) Z,Z • D) Z,E

  6. Question 8 • Rank the following alkenes in order of decreasing heat of combustion: • A)3 > 1 > 2 • B)2 > 3 > 1 • C)1 > 2 > 3 • D)2 > 1 > 3

  7. Question 3 • What is the major product of the dehydration of 2-methylcyclohexanol? • A)1-methylcyclohexene • B)2-methylcyclohexene • C)3-methylcyclohexene • D)cyclohexene

  8. Question 14 • How many alkenes would you expect to be formed from the E2 elimination of • 3-bromo-2-methylpentane? • A)2 • B)3 • C)4 • D)5

  9. Question 4 • The major product of the dehydration of 1-phenyl-2-propanol is • A) B) • C) D)

  10. Question 10 • What is the major product in the reaction of 2-methyl-2-butanol with H2SO4 at 80°C? • A) B) • C) D)

  11. Question 11 • The reaction of 2-bromobutane with KOCH2CH3 in ethanol produces trans-2-butene. If the concentration of both reactants is doubled, what would be the effect on the rate of the reaction? • A) halve the rate • B) double the rate • C) quadruple the rate • D) no effect on the rate

  12. Question 12 • Which would react with KOCH2CH3 in ethanol faster? • A)cis-2-tert-butylcyclohexyl bromide • B)trans-2-tert-butylcyclohexyl bromide

  13. Question 13 • Which would react with KOC(CH3)3/(CH3)3COH faster? • A)cis-3-tert-butylcyclohexyl bromide • B)trans-3-tert-butylcyclohexyl bromide

  14. Question 18 • Which one of the following best describes a mechanistic feature of the reaction of • 3-bromopentane with sodium ethoxide? • A) The reaction occurs in a single step which is bimolecular. • B) The reaction occurs in two steps, both of which are unimolecular. • C) The rate-determining step involves the formation of the carbocation (CH3CH2)2CH+. • D) The carbon-halogen bond breaks in a rapid step that follows the rate-determining step.

  15. Question 19 • Which of the following statements is false? • A) tert-Butyl alcohol reacts with sodium faster than 1-butanol. • B) tert-Butyl alcohol reacts with hydrogen bromide faster than sec-butyl alcohol. • C) tert-Butyl alcohol undergoes acid-catalyzed dehydration faster than sec-butyl alcohol does. • D) tert-Butyl alcohol undergoes E2 elimination faster than tert-butyl fluoride does.

  16. Question 21 • Which reaction would be most likely to proceed by an E1 mechanism? • A) 2-chloro-2-methylbutane + NaCH2CH3 in ethanol (heat) • B) 1-bromo-2-methylbutane + KOC(CH3)3 in DMSO • C) 2-bromo-2-methylbutane in ethanol (heat) • D) 2-methyl-2-butanol + K

  17. B A A C D A B D D B C A B A C A Answer Key – Chapter 5 C A A D C A B

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