16.4 Electrophilic Addition to Conjugated Dienes

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Kinetic Product

The Kinetic Product is the product formed with the lowest activation energy (most stable transition state).

-Focus on the most stable resonance contributor of the carbocation intermediate.

-It is the major product at lower temperatures and shorter reaction times.

Thermodynamic Product

The Thermodynamic Product is the most stable product (i.e. most substituted alkene in this context).

-It is the major product at higher temperatures and longer reaction times.

Kinetic Product

The Kinetic Product is the product formed with the lowest activation energy (most stable transition state).

-Focus on the most stable resonance contributor of the carbocation intermediate.

-It is the major product at lower temperatures and shorter reaction times.

PREDICTING THE PRODUCTS FOR ADDITION REACTIONS TO CONJUGATED DIENES
1. Start by identifying the resonance-stabilized carbocation intermediates. Discard/ignore the others.
2. Select the more stable carbocation (shares the positive charge on the more substituted carbon atoms).
3. Draw both possible products when the nucleophile adds to the two carbon that share the positive charge.
4. The product resulting from the nucleophile adding to the more substituted carbon is the kinetic product.
5. The product with the more substituted pi bond is the thermodynamic product.

Predict both the kinetic and thermodynamic products of the following reaction.

addition to conjugated dienes
kinetic vs thermodynamic product

Pericyclic Reactions

1. Cycloaddition Reactions

cycloaddition reactions

2. Electrocylic Reactions

electrocylic reactions

3. Sigmatropic Rearrangements

sigmatropic rearrangements