16.5 Diels Alder Reactions

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    Pericyclic Reactions

    Cycloaddition Reactions

    cycloaddition reactions

    Electrocyclic Reactions

    electrocylic reactions

    Sigmatropic Rearrangements

    sigmatropic rearrangements

    Diels-Alder Reactions

    -A 4 + 2 cycloaddition
    -concerted mechanism
    -syn addition between a dienophile and a conjugated diene

    diels-alder reaction mechanism

    Dienes

    -diene must be in the s-cis conformation
    -dienes are more reactive with electron-donating groups attached

    Rank the following dienes in decreasing order of reactivity in a Diels-Alder reaction.

    dienes 01
    dienes 02
    dienes 03
    dienes 04
    dienes 05

    Rank the following dienes in decreasing order of reactivity in a Diels-Alder reaction.

    dienes 06
    dienes 07
    dienes 08

    Dienophiles

    -dienophiles are more reactive with electron-withdrawing groups attached

    Rank the following dienophiles in decreasing order of reactivity in a Diels-Alder reaction.

    dienophile 01
    dienophile 02
    dienophile 03

    Stereoselectivity in Diels-Alder Reactions

    stereoselectivity of Diels-Alder Reactions 01
    stereoselectivity of Diels-Alder Reactions 02

    Predict the products for the following reactions.

    predict the products of Diels-Alder Reaction 01
    predict the products of Diels-Alder Reaction 02
    general stereoselectivity of diels-alder reactions

    Predict the products for the following reactions.

    predict the products of Diels-Alder Reaction 04
    predict the products of Diels-Alder Reaction 05

    Regioselectivity in Diels-Alder Reactions

    Only 1,2 and 1,4 products are observed with unsymmetrical reagents (relationship of D to W).

    regioselectivity of diels-alder reactions 01
    regioselectivity of diels-alder reactions 02

    Predict the products for the following reactions.

    predict the products of Diels-Alder Reaction 06
    predict the products of Diels-Alder Reaction 07

    Diels-Alder Reactions with Cyclic Dienes

    diels-alder reaction with cyclic dienes 02
    endo rule

    Predict the products for the following reactions.

    predict the products of Diels-Alder Reaction 08
    predict the products of Diels-Alder Reaction 09
    predict the products of Diels-Alder Reaction 10

    Conservation of Orbital Symmetry

    conservation of orbital symmetry diels-alder reaction 01
    conservation of orbital symmetry diels-alder reaction 02