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Chemistry LibreTexts

8.E: Alkenes: Reactions and Synthesis (Exercises)

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    61713
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    These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry textbook.

    8.1 Preparation of Alkenes: A Preview of Elimination Reactions

    8.1 Exercises

    Questions

    Q8.1.1

    In elimination reactions there tends to have a mixture of products. What are the two possible alkene products for the reaction of 2-bromo-2-methylpentane with NaOH?

    Q8.1.2

    Predict the E/Z isomers for the following molecule when reacted with H2SO4.

    Solutions

    S8.1.1

    8.1.png

    S8.1.2

    8.2 Halogenation of Alkenes: Addition of X2X2

    8.2 Exercises

    Questions

    Q8.2.1

    Predict the products for 1,2-dimethylcyclopentene reacting with Br2 with proper stereochemistry.

    Q8.2.2

    Predict the products for 1,2-dimethylcyclpentene reacting with HCl, give the proper stereochemistry. What is the relationship between the two products?

    Solutions

    S8.2.1

    8.2.png

    S8.2.2

    These compounds are enantiomers.

    8.3: Halohydrins from Alkenes: Addition of HOX

    8.3 Exercises

    Questions

    Q8.3.1

    Predict the product of the following reaction:

    Q8.3.2

    When butene is treated with NBS in the presence of water, the product shows that the bromine is on the least substituted carbon, is this Markovnikov or anti-Markovnikov?

    Solutions

    S8.3.1

    S8.3.2

    Since the bromine is the first addition to the alkene, this addition would be an anti-Markovnikov addition.

    8.4 Hydration of Alkenes: Addition of H2OH2O by Oxymercuration

    8.4 Exercises

    Questions

    Q8.4.1

    In each case, predict the product(s) of these reactants of oxymercuration.

    Q8.4.2

    Propose the alkene that was the reactant for each of these products of oxymercuration.

    Solutions

    S8.4.1

    S8.4.2

    8.6 Reduction of Alkenes: Hydrogenation

    8.6 Exercises

    Questions

    Q8.6.1

    Predict the products if the following alkenes were reacted with catalytic hydrogen.

    Solutions

    S8.6.1

    8.8 Oxidation of Alkenes: Cleavage to Carbonyl Compounds

    8.8 Exercises

    Questions

    Q8.8.1

    What would you expect the products to be from the reaction of cis-2-pentene with m-chloro-peroxybenzoic acid? Show the stereochemistry of the final product.

    Q8.8.2

    Give a reaction scheme with starting alkenes and required reagents to produce the following compounds.

    Solutions

    S8.8.1

    S8.8.2

    8.9 Addition of Carbenes to Alkenes: Cyclopropane Synthesis

    8.9 Exercises

    Questions

    Q8.9.1

    Predict the following products. Will they be the same product?

    Solutions

    S8.9.1

    No they will not be the same product, they will be isomers of each other.

    8.10 Radical Additions to Alkenes: Chain-Growth Polymers

    8.10 Exercises

    Questions

    Q8.10.1

    Propose the monomer units in the following polymers:

    Solutions

    S8.10.1

    8.13 Stereochemistry of Reactions: Addition of H2OH2O to a Chiral Alkene

    8.13 Exercises

    Questions

    Q8.13.1

    Predict the products of the following reaction showing stereochemistry.

    8.13qu.png

    Solutions

    S8.13.1

    8.13sol.png

    The products (Markovnikov) are diastereomers of one another.

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