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The original definition of meso is “an achiral compound

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

Solution for problem 41SP Chapter 5

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 41SP

The original definition of meso is “an achiral compound that has chiral diastereomers.” Our working definition of meso is “an achiral compound that has chirality centers (usually asymmetric carbon atoms).” The working definition is much easier to apply, because we don’t have to envision all possible chiral diastereomers of the compound. Still, the working definition is not quite as complete as the original definition.

(a) Show how cis-cyclooctene is defined as a meso compound under the original definition, but not under our working definition. (Review Figure 5-18.)

(b) See if you can construct a double allene that is achiral, although it has chiral diastereomers, and is herefore a meso compound under the original definition. The allene structure is not a chirality center, but it can be a chirality axis.

Step-by-Step Solution:
Step 1 of 3

Solution 41SP

(a)        cis-cyclooctene

It has no chirality center, so the working definition which states that a meso compound must have chirality center and it is not suitable here. This compound is meso, because it has internal mirror plane, so the original definition...

Step 2 of 3

Chapter 5, Problem 41SP 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 full solution covers the following key subjects: definition, compound, meso, original, working. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. The answer to “The original definition of meso is “an achiral compound that has chiral diastereomers.” Our working definition of meso is “an achiral compound that has chirality centers (usually asymmetric carbon atoms).” The working definition is much easier to apply, because we don’t have to envision all possible chiral diastereomers of the compound. Still, the working definition is not quite as complete as the original definition.(a) Show how cis-cyclooctene is defined as a meso compound under the original definition, but not under our working definition. (Review Figure 5-18.)(b) See if you can construct a double allene that is achiral, although it has chiral diastereomers, and is herefore a meso compound under the original definition. The allene structure is not a chirality center, but it can be a chirality axis.” is broken down into a number of easy to follow steps, and 127 words. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. The full step-by-step solution to problem: 41SP from chapter: 5 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Since the solution to 41SP from 5 chapter was answered, more than 441 students have viewed the full step-by-step answer.

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The original definition of meso is “an achiral compound

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