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6.22: Additional Exercises

  • Page ID
    182921
  • SN2

    7-1 Predict which compound in each pair would undergo the SN2 reaction faster.

    a) or

    b) or

    c) or

    d) or

    7-2 Predict the products of these nucleophilic substitution reactions, including stereochemistry when appropriate.

    a)

    b)

    c)

    d)

    7-3 Show how each compound might be synthesized using SN2 reaction.

    a)

    b)

    c)

    7-4 Show 2 ways to synthesize the ether below using SN2 reaction

    7-5 Of the two ways of synthesizing the compound in previous question (7-4), which one would be the most efficient? Why? Show the mechanism of the reaction as part of your explanation.

    7-6 Arrange the compounds below in increasing order of nucleophilicity.

    H2O; NH2-; CH3O-; CH3CH2O-

    SN1

    7-7 List the following carbocations in order of increasing stability.

    7-8 Give the solvolysis product expected when the compound is heated in methanol.

    a)

    b)

    c)

    d)

    7-9 Predict with compound in each pair will undergo an SN1 reaction more quickly.

    a) or

    b) or

    c) or

    d) or

    7-10 Show how the following carbocations would rearrange to become more stable. Draw the mechanism of the rearrangement.

    a)

    b)

    c)

    d)

    SN2 vs SN1

    7-11 Predict whether each compound below would be more likely to undergo a SN2 or SN1 reaction.

    a)

    b)

    c)

    d)

    7-12 Predict the product of the following reactions.

    a)

    b)

    c)

    d)

    7-13 Show how each compound may be synthesized using nucleophilic substitution reactions.

    a)

    b)

    c)

    d)

    e)

    f)

    g)

    E2 vs E1

    7-14 Predict the major products of the following reactions.

    a)

    b)

    c)

    7-15 Draw the expected major product when each of the following compounds is treated with hydroxide to give an E2 reaction.

    a)

    b)

    c)

    7-16 Predict all the elimination products of the following reactions and label the major product.

    a)

    b)

    c)

    d)

    Substitution vs Elimination

    7-17 Identify the function of the following reagents. The reagents will be a strong/weak nucleophile and/or a strong/weak base.

    a) Cl-

    b) NaH

    c) t-BuO-

    d) OH-

    e) H2O

    f) HS-

    g) MeOH

    7-18 Identify which mechanism the following reactions would undergo.

    a)

    b)

    c)

    d)

    e)

    7-19 Identify all the products of the following reactions and specify the major product.

    a)

    b)

    c)

    d)

    e)

    7-20 The following reaction yields five different products. Give the mechanisms for how each is formed.