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A chemist finds that the addition of (+)-epinephrine to

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

Solution for problem 13P 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 13P

A chemist finds that the addition of (+)-epinephrine to the catalytic reduction of butan-2-one(Figure 5-16) gives a product that is slightly optically active, with a specific rotation of +0.45°.Calculate the percentages of (+)-butan-2-ol and (-)-butan-2-ol formed in this reaction.

Step-by-Step Solution:

Solution 13P :

Step 1:

Given :

Observed specific rotation of butan-2-ol = +0.45°.

Percentages of (+)-butan-2-ol and (-)-butan-2-ol formed in this reaction = ?

The rotation of pure butan-2-ol = +13.5 %

We know formula for optical purity :

                Optical purity(o.p) = 100 %

        Hence , o.p for butan-2-ol  = 100 %

                                            = 3.33 % 

Therefore, the o.p of butan-2-ol is 3.33 % which also means that the enantiomeric excess(e.e) is 3.33 % excess  (+) enantiomer over (-) enantiomer.

Step 2:

Now, let’s calculate the percentages of (+) and (-) enantiomer in the mixture :

Let’s put it in the equation from and solve it :

        

                (+) + (-) = 100 %          -------------- (1)

                (+) - (-) = 3.33 %          -------------- (2)

        

We can rewrite equation (1) as :

                (-) = 100 % - (+)         ----------- (3)

Using equation (3), we can rewrite equation (2) as :

                (+) - (100 % - (+)) = 3.33 %

        The above equation can be simplified as :

                2 (+)  = 3.33 % + 100 %

                2(+)  = 103.33 %

                       (+) =

                       (+)         = 51.66 %

Hence, the percentages of (+)-butan-2-ol formed in the reaction is 51.66 %

Step 3 of 3

Chapter 5, Problem 13P is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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