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Chemistry / Organic Chemistry 2 / Chapter 19 / Problem 19.71

Organic Chemistry | 2nd Edition | ISBN: 9781118454312 | Authors: David R. Klein

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Aromatic heterocycles are also capable of undergoing

Chapter 19, Problem 19.71

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QUESTION:

Aromatic heterocycles are also capable of undergoing electrophilic aromatic substitution. For example, when furan is treated with an electrophile, an electrophilic aromatic substitution reaction occurs in which the electrophile is installed exclusively at the C2 position. Explain why this reaction occurs at the C2 position, rather than the C3 position. O E O 2 3 E !

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QUESTION:

Aromatic heterocycles are also capable of undergoing electrophilic aromatic substitution. For example, when furan is treated with an electrophile, an electrophilic aromatic substitution reaction occurs in which the electrophile is installed exclusively at the C2 position. Explain why this reaction occurs at the C2 position, rather than the C3 position. O E O 2 3 E !

ANSWER:

Step 1 of 2

This exercise tells us that aromatic heterocycles are also capable of undergoing electrophilic aromatic substitution. As an example, when furan is treated with an electrophile, an electrophilic aromatic substitution reaction occurs which installs the electrophile at the C2 position.

We’re asked to explain why this reaction occurs exclusively at the C2 position, rather than at the C3 position.

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