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    Zaitsev's Rule and Hoffman's Rule describe which alkene will be the major product of an elimination reaction. Zaitsev's Rule states that the more highly substituted alkene will be favored, while Hoffman's Rule favors the less substituted. The determining factor is the amount of steric hindrance of the base - if it is bulky, like tert-butoxide, Hoffman's Rule will apply due to difficulty interacting with the more substituted carbon. If the base is less hindered, like hydroxide, Zaitsev's Rule will apply and the more substituted alkene will be the major product.

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    Zaitsev's Rule and Hoffman's Rule describe which alkene will be the major product of an elimination reaction. Zaitsev's Rule states that the more highly substituted alkene will be favored, while Hoffman's Rule favors the less substituted. The determining factor is the amount of steric hindrance of the base - if it is bulky, like tert-butoxide, Hoffman's Rule will apply due to difficulty interacting with the more substituted carbon. If the base is less hindered, like hydroxide, Zaitsev's Rule will apply and the more substituted alkene will be the major product.

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    Suraj.

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    Zaitsev's Rule and Hoffman's Rule describe which alkene will be the major product of an elimination reaction. Zaitsev's Rule states that the more highly substituted alkene will be favored, while Hoffman's Rule favors the less substituted. The determining factor is the amount of steric hindrance of the base - if it is bulky, like tert-butoxide, Hoffman's Rule will apply due to difficulty interacting with the more substituted carbon. If the base is less hindered, like hydroxide, Zaitsev's Rule will apply and the more substituted alkene will be the major product.

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    28 views1 page

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    Nehal Kumar
    Zaitsev's Rule and Hoffman's Rule describe which alkene will be the major product of an elimination reaction. Zaitsev's Rule states that the more highly substituted alkene will be favored, while Hoffman's Rule favors the less substituted. The determining factor is the amount of steric hindrance of the base - if it is bulky, like tert-butoxide, Hoffman's Rule will apply due to difficulty interacting with the more substituted carbon. If the base is less hindered, like hydroxide, Zaitsev's Rule will apply and the more substituted alkene will be the major product.

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    Zaistev’s Rule versus Hoffman’s Rule

    Zaitsev’s Rule: The major elimination product is the more highly substituted alkene (Hardinger
    77).

    Hofmann’s Rule: The major elimination product is the less highly substituted alkene (Hardinger
    78).

    So which one applies?

    It is dependent on how much steric hindrance there is at the end of the base that directly
    interacts with the beta hydrogen.

    For example: the base tert-butoxide, (CH3)3CO- has a lot of steric hindrance.
    As a result, the carbon with more steric hindrance won’t favorably occupy
    the same region of space as tert-butoxide, and it’s harder for the negatively-
    charged oxygen to reach that carbon’s beta hydrogens (Hardinger 78).

    Therefore, it’s more energetically-favorable for the tert-butoxide to attack the


    beta hydrogen on the less-substituted carbon.

    In this case, Hofmann’s Rule would dominate because of the amount of steric hindrance of
    the base, and the major product is the less highly substituted alkene.

    If the base does not have significant steric hindrance, such as -OH, then Zaitsev’s Rule
    dominates and the major product is the more highly substituted alkene. This is because the
    oxygen of the base has only a hydrogen bonded to it, which doesn’t cause as much hindrance
    as the base moves to attack the beta hydrogens. Therefore, the base is able to maneuver
    around the nucleophile’s substituents more freely and carry out the reaction.

    Note: E1 reactions always proceed according to Zaitsev’s Rule.

    Note: Steric hindrance is only relevant at the business end of the base (Hardinger 78).

    Hardinger, Steven. “Chemistry 14D Lecture Supplement” 4th Ed. Hayden McNeil. 2016. Print.

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