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When optically pure (R)-2-bromobutane is heated with

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

Solution for problem 12P 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 12P

When optically pure (R)-2-bromobutane is heated with water, butan-2-ol is the product. The reaction forms twice as much (S)-butan-2-ol as (R)-butan-2-ol. Calculate the e.e. and the specific rotation expected for the product.

Step-by-Step Solution:

Solution 12P :

Step 1:

The enantiomeric excess (e.e.) is a method for expressing the relative amounts of enantiomers in a mixture. This can be calculated using the formula as shown below :

e.e. =  100% =  100%

The specific rotation is defined as the rotation found using a 10-cm (1-dm) sample cell and a concentration of 1 g/mL. It is denoted by []. It is calculated using the formula :

         [] =

Where,  = rotation observed in the polarimeter.

         c = concentration in g/mL.

         l = length of sample cell in dm(decimeter).

Step 2:

Given reaction :

The reaction produces twice as much as (S)-(+)butan-2-ol(d- enantiomer) as (R)-(-)butan-2-ol(l- enantiomer)

        i.e , d = 2l

Now, let’s calculate the e.e :

e.e. =  100%

This can be rewritten as :

e.e =  100%

              =   100%

          e.e   = 33.3 %.

Therefore, the e.e expected for the product is 33.3 %.

Step 3 of 3

Chapter 5, Problem 12P is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

This full solution covers the following key subjects: butan, Product, optically, Expected, forms. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. The answer to “When optically pure (R)-2-bromobutane is heated with water, butan-2-ol is the product. The reaction forms twice as much (S)-butan-2-ol as (R)-butan-2-ol. Calculate the e.e. and the specific rotation expected for the product.” is broken down into a number of easy to follow steps, and 32 words. Since the solution to 12P from 5 chapter was answered, more than 1460 students have viewed the full step-by-step answer. The full step-by-step solution to problem: 12P from chapter: 5 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. 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.

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