Organic Chemistry

Learn the toughest concepts covered in Organic Chemistry with step-by-step video tutorials and practice problems by world-class tutors.

11. Radical Reactions

Radical Selectivity

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Not all radicals are born equal! Some of them are going to make pretty smart decisions from an energy perspective, while others are a little on the crazy side. Let’s turn to some potential role models for guidance on this topic. 

Drinking Responsibly vs. Getting Destroyed:

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Radical selectivity:Alcoholics Anonymous Version

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Selectivity is defined as the ability to only halogenate the carbons with most stable radical intermediates.

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Predict the product of the following Radical Halogenation. Would the following reaction be synthetically useful? (Yielding only one product). 

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Predict the Product.

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Predict the product of the following Radical Halogenation. Would the following reaction be synthetically useful? (Yielding only one product). 

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Predict the Product.

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Predict the product of the following Radical Halogenation. Would the following reaction be synthetically useful? (Yielding only one product). 

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Predict the Product.

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Predict the product of the following Radical Halogenation. Would the following reaction be synthetically useful? (Yielding only one product). 

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Predict the Product.

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Hammond’s Explanation:

Early transition states could care less what they look like, whereas late transition states have to be much more careful about the arrangements they take. 

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Using the Hammond Postulate to describe radical chlorination.

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Using the Hammond Postulate to describe radical bromination.

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