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8.19: Additional Exercises

  • Page ID
    182958
  • Addition of Hydrogen Halides to Alkenes

    9-1 Give the IUPAC name for the product of the following reaction.

    9-2 Draw the reaction mechanism of the previous problem (9-1).

    9-3 Identify the product of the following reactions.

    9-4 Identify the products of the following reactions.

    Addition of Water: Hydration of Alkenes

    9-5 Identify the product of the following reactions.

    9-6 Identify the product of the following reaction.

    9-7 Propose a plausible route of synthesis for the following product starting with 1-butanol.

    9-8 Which of the following alkenes can be used to obtain 3,4-dimethylpentan-2-ol through a hydration reaction using dilute acid?

    a) (2Z)-3,4-dimethylpent-2-ene

    b) 3,4-dimethylpent-1-ene

    c) 2,3,4-trimethylpent-2-ene

    d) 2,4-dimethyl-3-methylidenepentane

    Hydration by Oxymercuration-Demercuration

    9-9 Explain why hydration of an alkene by Oxymercuration-Demercuration gives the Markovnikov product.

    9-10 Identify the products of the following reactions.

    9-11 Identify the product of the following reaction.

    9-12 Propose a possible route of synthesis for the following ether starting with 2-ethylbutan-1-ol.

    9-13 Give the IUPAC name of the product of the following reaction.

    a) 2-methylpropan-2-ol

    b) 2,2-dimethylbutane

    c) 2-methoxy-2-methylpropane

    d) 1,1-dimethylcyclopropane

    Hydroboration of Alkenes

    9-14 Identify the products of the following reactions.

    9-15 Identify the products of the following reactions.

    9-16 Give the IUPAC name for the product of the following reaction.

    Addition of Halogens to Alkenes

    9-17 Identify the products of the following reactions.

    9-18 Identify the product of the following reaction.

    9-19 What is the product of the following reaction?

    a) (2Z)-2-bromo-3-methylpent-2-ene

    b) 2-bromo-3-methylpentane

    c) 2,3-dibromo-3-methylpentane

    d) (2E)-4-bromo-3-methylpent-2-ene

    9-20 What reagents can be used in each step to obtain the following products?

    9-21 Explain why you do not obtain a mixture of cis- and trans-brominated products when you react Br2/CCl4 with cyclopentene.

    Formation of Halohydrins

    9-22 Identify the product of the following reaction, making sure to include stereochemistry.

    9-23 Draw the mechanism of the reaction in the previous problem (9-22).

    9-24 Give the IUPAC name for the product of the following reaction.

    9-25 Identify the product of the following reaction.

    Catalytic Hydrogenation of Alkenes

    9-26 Identify the products of the following reactions.

    9-27 Suggest a possible route of synthesis, that includes a catalytic hydrogenation step, to obtain the following product.

    9-28 Identify the product of the following reaction.

    9-29 Identify the product of the following reaction, making sure to include stereochemistry.

    Addition of Carbenes to Alkenes

    9-30 Identify the product of the following reaction.

    9-31 Identify the product(s) of the following reaction.

    9-32 Identify the product of the reaction when (2E)-3-methylhex-2-ene reacts with the carbene product from the previous problem (9-31), then reacts with Br2 and hv.

    9-33 Propose a possible route of synthesis for the following reaction.

    9-34 Identify the product of the following reaction.

    Epoxidation of Alkenes and Acid-Catalyzed Opening of Epoxides

    9-35 Identify the product of the following reaction.

    9-36 Identify the product of the following reactions, specifying stereochemistry where appropriate.

    9-37 Identify the products of the following reaction, including stereochemistry.

    9-38 What is the product of the following reaction?

    a) benzoic acid

    b) 1-cyclohexylethan-1-ol

    c) 1-cyclohexylethan-1-one

    d) cyclohexanol

    9-39 What is the product of the following reaction?

    a) 4-chlorobutane-1,3-diol

    b) 3-chlorobutan-1-ol

    c) 2-chlorobutane-1,4-diol

    d) 2,4-dichlorobutan-1-ol

    9-40 Draw the arrows for the following epoxidation reaction to show the movement of electrons.

    Syn Dihydroxylation of Alkenes

    9-41 Identify the product of the following reaction, including stereochemistry.

    9-42 Give the IUPAC name for the product(s) of the following reaction. Include stereochemistry.

    9-43 Identify the product of the following reaction.

    9-44 Suggest a possible route of synthesis for the following compound starting with cyclopentanol.

    Oxidative Cleavage of Alkenes

    9-45 Identify the products of the following reactions.

    9-46 Identify the products of the following reactions.

    9-47 Identify the product of the following reaction.

    Polymerization of Alkenes

    9-48 Identify the alkene monomer that composes the following polymer.

    9-49 Draw the mechanism for the acid catalyzed formation of the polymer in the previous problem (9-48).

    9-50 Draw the resulting polymer of the following reaction. Draw the chain four monomers in length.