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3,4-Dimethylpent-1-ene has the formula When pure

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

Solution for problem 38SP 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 38SP

3,4-Dimethylpent-1-ene has the formula  When pure (R)-3,4-dimethylpent-1-ene is treated with hydrogen over a platinum catalyst, the product is (S)-2,3-dimethylpentane.

(a) Draw the equation for this reaction. Show the stereochemistry of the reactant and the product.

(b) Has the chirality center retained its configuration during this hydrogenation, or has it been inverted?

(c) The reactant is named (R), but the product is named (S). Does this name change imply a change in the spatial arrangement of the groups around the chirality center? So why does the name switch from (R) to (S)?

(d) How useful is the (R) or (S) designation for predicting the sign of an optical rotation? Can you predict the sign of the rotation of the reactant? Of the product? (Hint from Juliet Capulet: “What’s in a name? That which we call a rose/By any other name would smell as sweet.”)

Step-by-Step Solution:

Solution 38SP

Step 1 </p>

Step 2 </p>

(b)        There was an inversion in the configuration of the chiral centre during the

             hydrogenation.

Step 3 of 4

Chapter 5, Problem 38SP is Solved
Step 4 of 4

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

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3,4-Dimethylpent-1-ene has the formula When pure

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