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A student synthesized Compound 1 (below). To purify the

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

Solution for problem 47SP 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 47SP

A student synthesized Compound  (below). To purify the compound, he extracted it into aqueous base and then acidified the solution to protonate the acid so that he could extract it back into ether. When he evaporated the ether, he found that his product had been converted entirely into Compound

         

(a) What is the functional group that forms the ring in Compound 1? In Compound 2?

(b) How many carbon atoms are there in Compound 1? In Compound 2? Where did the other carbon atoms go?

(c) When did the reaction occur: When the student added the base, or when he added the acid?

(d) Propose a mechanism for the conversion of Compound 1 to Compound 2.

Step-by-Step Solution:
Step 1 of 3

Solution 47SP

(a) The functional group in compound 1 is acetal. The functional group in compound 2 is ester (lactone).

(b) Compound 1 has 8 carbons and compound 2 has 6 carbons. Two carbons have been lost because two carbons of acetyl have been cleaved.

(c) Acetals are stable to base, so the acetal must have been cleaved when acid was added.

(d) Mechanism:

The lone pair of electrons of oxygen of compound 1 abstracts proton to form an oxonium ion by cleaving of ring.

Step 2 of 3

Chapter 20, Problem 47SP is Solved
Step 3 of 3

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

Organic Chemistry was written by and is associated to the ISBN: 9780321768414. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. This full solution covers the following key subjects: compound, atoms, added, DID, Ether. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Since the solution to 47SP from 20 chapter was answered, more than 347 students have viewed the full step-by-step answer. The answer to “?A student synthesized Compound (below). To purify the compound, he extracted it into aqueous base and then acidified the solution to protonate the acid so that he could extract it back into ether. When he evaporated the ether, he found that his product had been converted entirely into Compound (a) What is the functional group that forms the ring in Compound 1? In Compound 2?(b) How many carbon atoms are there in Compound 1? In Compound 2? Where did the other carbon atoms go?(c) When did the reaction occur: When the student added the base, or when he added the acid?(d) Propose a mechanism for the conversion of Compound 1 to Compound 2.” is broken down into a number of easy to follow steps, and 113 words. The full step-by-step solution to problem: 47SP from chapter: 20 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM.

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A student synthesized Compound 1 (below). To purify the