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Furan undergoes electrophilic aromatic substitution more

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 57SP Chapter 17

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 57SP

Problem 57SP

Furan undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient. For example, furan reacts with bromine to give 2-bromofuran.

(a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms of each sigma complex, and compare their stabilities.

(b) Explain why furan undergoes bromination (and other electrophilic aromatic

substitutions) primarily at the 2-position.

Step-by-Step Solution:
Step 1 of 3

Solution 57SP

(a)        Formation of 2-bromofuran from furan -

(b)        furan undergoes electrophilic aromatic substitution at the 2-position. Attack of the electrophile of the electrophile  at 3-position in furan leads to an intermediate with only two resonance structures. Three resonance structures are possible for the intermediate produced by attack at 2-position. That is; the intermediate produced by attack at 2-postion is more stable. This is the reason that electrophilic attack occurs at 2-position rather than at 3-position in furan.

Step 2 of 3

Chapter 17, Problem 57SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. This full solution covers the following key subjects: furan, position, aromatic, bromination, undergoes. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The full step-by-step solution to problem: 57SP from chapter: 17 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Since the solution to 57SP from 17 chapter was answered, more than 1209 students have viewed the full step-by-step answer. The answer to “Furan undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient. For example, furan reacts with bromine to give 2-bromofuran.(a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms of each sigma complex, and compare their stabilities.(b) Explain why furan undergoes bromination (and other electrophilic aromaticsubstitutions) primarily at the 2-position.” is broken down into a number of easy to follow steps, and 63 words.

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Furan undergoes electrophilic aromatic substitution more