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Exercises: Radical substitution in allylic position

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Fig.1

Exercise

Depending on the conditions, the reactions of propene with either bromine or chlorine, respectively, yields different products. Which statements are correct?

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At high temperature or low halogen concentration, mainly a radical substitution of hydrogen at the methyl group occurs.

At low temperature or high halogen concentration, mainly a radical substitution of hydrogen at the methyl group occurs.

At low temperature, addition of the halogen to the double bond occurs.

At high temperature, addition of the halogen to the double bond occurs.

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Exercise

What is the position in immediate vicinity to the double bond called?

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Benzylic.

Allylic.

Vinylic

Alkylic.

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Exercise

Which of the following statements are correct?

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Allyl radicals and allyl cations are considerably resonance-stabilized.

While allyl radicals are not particularly resonance-stabilized, allyl cations are.

The resonance stabilization of allylic systems may be illustrated by comparing the dissociation energies of different types of C-H bonds.

The considerable resonance stabilization of allyl radicals and allyl cations is caused by the overlapping of the p orbitals of the three vicinal sp3 hybridized carbon atoms.

The considerable resonance stabilization of allyl radicals and allyl cations is caused by the overlapping of the p orbitals of the three vicinal sp2 hybridized carbon atoms.

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Exercise

What are the consequences of the resonance of the propenyl radical's allylic system?

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Due to the resonance, all hydrogen atoms display alkylic character. Only the hydrogen at the central carbon is allylic.

The equal lengths of the propenyl radical's C-C bonds are the result of the resonance of allylic systems.

Due to the resonance, all four terminal hydrogen atoms display allylic character. Only the hydrogen at the central carbon is vinylic.

The resonance of allylic systems results in different lengths of the propenyl radical's C-C bonds.

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