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    Organic Reaction Mechanisms

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    Written Assignment 6

    Submit your solutions to the following problems. Show all work where applicable .Answers alone are not acceptable.

    1. Select an alkyl halide and a nucleophile that will give each of the following products:

    a. CH3C≡CCH2CH3
    b. CH3CH2OCH2CH3
    c. CH3CH2SCH3
    d. (CH3)2CHCH2OH

    2. Draw out each of the following equations in a way that shows clearly the stereochemistry of the reactants and products.

    a. (R)-3-chlorohexane+sodium methoxide(in methanol) 3-methoxyhexane
    b. (S)-2-chlorobutane+methanol 2-methoxybutane

    3. Determine the order of reactivity for (CH3)2CHCH2Br, (CH3)3CBr, and CH3CHBrCH2CH3
    Reacting with

    a. CH3OH(methanol)
    b. NaSH(sodium hydrosulfide)

    4. Tell ALL possible products you expect and by what mechanism they are formed for each of the following reactions:


    5. Give the structures of all possible products when 2-chlorobutane reacts by the E-2 mechanism.

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    Solution Summary

    This solution offers rationale and guidelines to some representative problems on organic reaction mechanisms.