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Oxidation of a primary alcohol to an aldehyde usually

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

Solution for problem 6P Chapter 20

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 6P

Oxidation of a primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

(a) Show how you would use acid–base extraction to purify the pentanal.

(b) Which of the expected impurities cannot be removed from pentanal by acid–base extractions? How would you remove this impurity?

Step-by-Step Solution:
Step 1 of 3

Solution 6P

(a) The reaction mixture contains pentan-1-ol, pentanal, pentanoic acid, and pyridinium chlorochromate. This mixture can be separated by acid-case. Extraction. The purification of pentanal is given below.

(b) Pentan-1-ol cannot be removed from the pentanal by acid-base extraction. These two remaining products can be separated by distillation, the alcohol having the higher boiling point because for hydrogen bonding.

Step 2 of 3

Chapter 20, Problem 6P is Solved
Step 3 of 3

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

This full solution covers the following key subjects: acid, pentanal, oxidation, base, impurity. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. The full step-by-step solution to problem: 6P from chapter: 20 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. The answer to “Oxidation of a primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.(a) Show how you would use acid–base extraction to purify the pentanal.(b) Which of the expected impurities cannot be removed from pentanal by acid–base extractions? How would you remove this impurity?” is broken down into a number of easy to follow steps, and 56 words. Since the solution to 6P from 20 chapter was answered, more than 344 students have viewed the full step-by-step answer. Organic Chemistry was written by and is associated to the ISBN: 9780321768414.

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Oxidation of a primary alcohol to an aldehyde usually