Chapter 6

Which of the following best describes the carbon-chlorine bond of an alkyl chloride? A) nonpolar; no dipole B) polar; d+ at carbon and d- at chlorine C) polar; d- at carbon and d+ at chlorine D) ionic E) none of the above

Which of the following is classified as a vinylic halide? A) CH3CH=CHOH B) CH3CH=CHCl C) CH3CH=CHCH2Cl D) CH3CH2CH2CH2Br E) BrCH2CH=CH2

Which of the following is a secondary halide? A) ClCH2CH2C(CH3)3 B) ClCH2CH2CH(CH3)2 C) (CH3)2CClCH2CH3 D) (CH3)3CCHClCH3 E) ClCH2C(CH3)CH2CH3

Which of the following is a tertiary halide? A) ClCH2CH2C(CH3)3 B) ClCH2CH2CH(CH3)2 C) (CH3)2CClCH2CH3 D) (CH3)3CCHClCH3 E) ClCH2C(CH3)CH2CH3

Which of the following is a geminal dihalide? A) cis-1,2-dibromocyclopentane B) 3,3-dichloropentane C) trans-1,4-diiodocyclohexane D) isobutyl chloride E) 1,3-dibromoheptane

Which of the following is a vicinal dihalide? A) cis-1,2-dibromocyclopentane B) 3,3-dichloropentane C) trans-1,4-diiodocyclohexane D) isobutyl chloride E) 1,3-dibromoheptane

Which of the following is a secondary alkyl halide? A) methyl bromide B) isopropyl chloride C) t-butyl iodide D) propyl bromide E) isobutyl chloride

Which of the following is a primary alkyl halide? A) methyl bromide B) isopropyl bromide C) t-butyl iodide D) cyclohexyl bromide E) isobutyl chloride

Which of the following best describes DDT? A) a chlorocarbon used to decaffeinate coffee beans B) a polybrominated organic compound used as a herbicide C) a Freon used as a foaming agent D) a mixed alkyl halide used as an anesthetic E) a polychlorinated organic compound used as an insecticide

Which of the following alkyl halides has the smallest molecular dipole moment? A) CH3F B) CH3Cl C) CH2I2 D) CH2Cl2 E) CF4

Among the following alkyl halides, choose the one with the lowest boiling point. A) t-butyl chloride B) n-butyl chloride C) t-butyl bromide D) n-butyl iodide E) t-butyl iodide

When 2,2-dimethylbutane is subjected to free-radical chlorination, \_\_\_\_\_\_\_\_ distinct monochlorinated products are possible and \_\_\_\_\_\_\_\_ of these contain asymmetric carbon atoms. A) 4, 2 B) 5, 0 C) 3, 0 D) 5, 2 E) 4, 0

What type of intermediate is present in the SN2 reaction of cyanide with bromoethane? A) carbocation B) free radical C) carbene D) carbanion E) This reaction has no intermediate.

Which of the following species is the least nucleophilic? A) H2O B) BF3 C) (CH3)3N D) CH3O- E) CN-

Which of the following compounds is the most nucleophilic? A) CH3SH B) CH3OH C) H2O D) CH3CO2H E) BF3

Which of the following factors is favorable for nucleophilicity but not basicity? A) highly polarizable B) low electronegativity C) negatively charged D) sterically hindered

Which of the following solvents could be described as polar and protic? A) ethanol B) acetonitrile C) dimethylformamide D) acetone E) 18-crown-6

Which of the following compounds will undergo an SN2 reaction most readily? A) (CH3)3CCH2I B) (CH3)3CCl C) (CH3)2CHI D) (CH3)2CHCH2CH2CH2I E) (CH3)2CHCH2CH2CH2Cl

Which of the following alkyl chlorides will undergo SN2 reaction most readily? A) 1-chloro-4-methylpentane B) 2-chloro-4-methylpentane C) 2-chloro-3-methylpentane D) 3-chloro-2-methylpentane E) 2-chloro-2-methylpentane

Which of the following statements describe a favorable attribute of a leaving group? (More than one answer is possible.) A) The leaving group should be highly polarizable. B) The lower the electronegativity of the leaving group the better. C) Good leaving groups need to have low steric hindrance. D) The departed leaving group should have low basicity.

Which of the following alkyl halides reacts most rapidly via an SN2 reaction with NaCN? A) 1-iodohexane B) 1-fluorohexane C) (R)-2-bromohexane D) iodocyclohexane E) 1-iodo-1-methylcyclohexane

Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly? A) cyclohexyl bromide B) methyl iodide C) isopropyl chloride D) 3-chloropentane E) 3-iodo-3-methylpentane

Which of the following alkyl bromides undergoes solvolysis in aqueous methanol most rapidly? A) PhCHBrCH3 B) (CH3)2CHCH2CH2Br C) (CH3)2CHCH2CHBrCH3 D) CH3CH2CH2CH2Br E) PhBr

Which of the following alkyl halides reacts most rapidly via an SN1 solvolysis reaction in hot methanol? A) 1-iodohexane B) 1-fluorohexane C) (R)-2-bromohexane D) iodocyclohexane E) 1-iodo-1-methylcyclohexane