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Question 1

Question 1. Name the compound on the right according to the IUPAC system. A) 4-bromo-5-ethyl-2-methylheptane B) 4-bromo-3-ethyl-6-methylheptane C) 4-bromo-5-diethyl-2-methylpentane D) 4-bromo-3-ethyl-6-dimethylhexane. Question 2.

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Question 1

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  1. Question 1 • Name the compound on the right according to the IUPAC system. • A)4-bromo-5-ethyl-2-methylheptane • B)4-bromo-3-ethyl-6-methylheptane • C)4-bromo-5-diethyl-2-methylpentane • D)4-bromo-3-ethyl-6-dimethylhexane

  2. Question 2 • Name the compound on the right according to the IUPAC system. • A)3,4-dimethyl-2-hydroxypentane • B)2,3-dimethyl-4-pentanol • C)3,4-dimethyl-2-pentanol • D)2,3-dimethylpentyl-2-alcohol

  3. Question 3 • Name the compound on the right according to the IUPAC system. • A)trans-2-methylhydroxypentanol • B)trans-2-methylcyclopentanol • C)cis-2-methylhydroxypentanol • D)cis-2-methylcyclopentanol

  4. Question 4 • What type of alcohol is 2-methyl-3-pentanol? • A)primary (1°) • B)secondary (2°) • C)tertiary (3°) • D)quaternary (4°)

  5. Question 7 • What is the rate-determining step in the reaction of cyclobutanol with HCl? • A)protonation of the OH group • B)attack of the bromide on the carbocation • C)simultaneous formation of the C-Br bond and the breaking of the C-OH bond • D)carbocation formation

  6. Question 9 • Select the most stable carbocation. • A) B) • C) D)

  7. Question 14 • Which of the following is the least able to serve as a nucleophile in a chemical reaction? • A)Br- • B)OH- • C)NH3 • D)CH3+

  8. Question 15 • The species shown below represents _____ of the reaction between isopropyl alcohol and • hydrogen bromide. • A) the alkyloxonium ion intermediate • B) the transition step of the bimolecular proton transfer • C) the transition state of the attack of the nucleophile on the carbocation • D) the transition state of the unimolecular dissociation

  9. Question 10 • How many monochlorination products do you expect to obtain from the chlorination of • 2-methylbutane? • A)two • B)three • C)four • D)five

  10. Question 11 • The step shown below is the _____________ step of the free-radical chlorination of • chloromethane. • A)initiation • B)propagation • C)chain-terminating • D)bond cleavage

  11. Question 12 • What is the major product of the radical bromination of 1-tert-butylcyclopentane? • A) B) • C) D)

  12. Question 17 • How many monohalogenation products are possible? (Do not consider stereoisomers.) • A)2 • B)3 • C)4 • D)5

  13. Question 16 • For the free-radical reaction below, light is involved in which of the following reaction • steps? • A)Initiation only • B)Propagation only • C)Termination only • D)Initiation and propagation

  14. Question 19 • Which of the following best describes a mechanistic feature of the free-radical bromination (Br2, light) of 2-methylpropane? • A) The initiation step involves cleavage of a C-H bond. • B) The free-radical (CH3)3C· is produced in one propagation step and reacts with Br2 in another. • C) The reaction is characterized by the homolytic cleavage of the C-Br bond. • D) The reaction is concerted; i.e., it occurs in a single step.

  15. Question 13 • Which one of the following reacts with HBr at the fastest rate? • A) B) • C) D)

  16. A C B B D B D B C C B D C D D A C C B D Answer Key – Chapter 4

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