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Chemistry LibreTexts

10.E: Organohalides (Exercises)

  • Page ID
    61715
  • These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry textbook.

    10.1 Names and Properties of Alkyl Halides

    10.1 Exercises

    Questions

    Q10.1.1

    Give the names of the following organohalides:

    Q10.1.2

    Draw the structures of the following compounds:

    A – 2-Chloro-3,3-dimethylpentane

    B – 1,1-Dichloro-4-isopropylcyclohexane

    C – 3-bromo-3-ethylhexane

    Solutions

    S10.1.1

    A – 5-ethyl-4-iodo-3methyl-octane

    B – 1-bromo-2,3,4-trimethyl-pentane

    C – 4-bromo-5-chloro-2-methyl-heptane

    S10.1.2

    10.2 Preparing Alkyl Halides from Alkanes: Radical Halogenation

    10.2 Exercises

    Questions

    Q10.2.1

    Predict the mono-substituted halogenated product(s) of chlorine gas reacting with 2-methylbutane.

    Q10.2.2

    Predict the relative amount of each mono-brominated product when 3-methylpentane is reacted with Br2. Consider 1°, 2°, 3° hydrogen.

    Solutions

    S10.2.1

    S10.2.2

    10.4 Stability of the Allyl Radical: Resonance Revisited

    10.4 Exercises

    Questions

    Q10.4.1

    The following reaction shows the major product. Explain why this would be the final product and why the 2° bromo product is not the major product.

    Q10.4.2

    Predict the products of the following reactions:

    Solutions

    S10.4.1

    The product (A) is a 1° halogen which is more predominant product even though the (B) had a better transition state with a 2° radical. The 1° radical intermediate is not as sterically hindered.

    S10.4.2

    10.5 Preparing Alkyl Halides from Alcohols

    10.5 Exercises

    Questions

    Q10.5.1

    Predict the alcohol required for the synthesis of the following halides:

    Solutions

    S10.5.1

    10.6 Reactions of Alkyl Halides: Grignard Reagents

    10.6 Exercises

    Questions

    Q10.6.1

    How strong of a base would you expect ethyl Grignard to be? Would the following reactions be able to take place?

    Q10.6.2

    How would you make a deuterated compound from an alkyl halide?

    Solutions

    S10.6.1

    Because hydrocarbons like ethane are very weak acids (pKa = 50), then the corresponding carbanion (CH3CH2-) is expected to be a strong base. Both reactions will occur.

    S10.6.2

    By first making a Grignard and then exposing it to heavy water.

    10.8 Oxidation and Reduction in Organic Chemistry

    10.8 Exercises

    Questions

    Q10.8.1

    In each case state whether the reaction is an oxidation or reduction of the organic compound.

    Solutions

    S10.8.1

    A – Reduction

    B – Oxidation