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1.13: Sn1 and Sn2 Reactions Exercises

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    1) Which of the following best represents the carbon-chlorine bond of methyl chloride?

    2) Provide a detailed, stepwise mechanism for the reaction below.

    3) Rank the species below in order of increasing nucleophilicity in hydroxylic solvents:

    CH3CO2- CH3S- HO- H2O

    4) Give a stereochemical structure of the product from the reaction between (S)-2-iodopentane and KCN in DMF (dimethyl formamide, a good polar solvent for ionic reagents).

    5) Consider the reaction of (CH3)3CO- with iodomethane. Will the reaction rate increase, decrease, or remain the same if the concentration of iodomethane is increased? Explain.

    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

    7) What is the major organic product in the following reaction?

    8) Would 2-chloropropane or 1-chloro-2,2-dimethylpropane undergo substitution faster with Na+ -CCH? Give the structure of the substitution product.

    9) t-butyl chloride undergoes solvolysis in 70% water/30% acetone at a rate slower than in 80% water/20% acetone. Explain.

    10) Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation.

    11) Sn2 reactions involving chiral electrophiles usually proceed with: A) inversion of configuration B) slightly more inversion than retention. C) slightly more retention then inversion. D) retention of configuration. E) equal amounts of inversion and retention of configuration

    12) Which compound undergoes solvolysis in aqueous ethanol most rapidly and why? Remember: solvolysis refers to ionization of the molecule aided by the solvent.

    cyclohexyl bromide

    isopropyl chloride

    methyl iodide



    13) Why does CH2=CHCHBrCH3 undergo solvolysis much more rapidly than 2-bromobutane?

    14) Provide the structure of the major organic products which result in the reaction below.

    15) What combination of reactants would be best to prepare CH3OCH(CH3)2 by an Sn2 reaction?

    16) The reaction between 2-iodohexane and ethanol to give a substitution product most likely follows an ______ mechanism.

    17) Which of the following alkyl halides is most likely to undergo rearrangement in an Sn1 reaction?

    A) 3-bromopentane

    B) 2-chloro-3,3-dimethylpentane

    C) 3-chloropentane

    D) bromocyclohexane

    E) 1-bromo-4-methylcyclohexane

    18) Which compound is most nucleophilic? A) CH3SH B) CH3OH C) H2O D) CH3CO2H E) BF3

    19) Which halide has the smallest dipole moment?

    A) CH3F B) CH3Cl C) CH2I2 D) CH2Cl2 E) CF4

    20) 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

    21) Arrange the substrates in order of increasing Sn2 reactivity with NaCN: Bromoethane, 1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-bromo-2-methylpentane.

    22) Arrange the following compounds in order of increasing reactivity toward ethanol solvolysis: t-butyl bromide, t-butyl iodide, isopropyl chloride, and methyl iodide.

    1.13: Sn1 and Sn2 Reactions Exercises is shared under a not declared license and was authored, remixed, and/or curated by Sergio Cortes.

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