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If you had the two enantiomers of carvone in unmarked

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

Solution for problem 11P 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 11P

If you had the two enantiomers of carvone in unmarked bottles, could you use just your nose and a polarimeter to determine:

(a) whether it is the (+) or (-) enantiomer that smells like spearmint?

(b) whether it is the (R) or (S) enantiomer that smells like spearmint?

(c) With the information given in the drawings of carvone above, what can you add to your answers to (a) or (b)?

Step-by-Step Solution:

Solution 11P :

Step 1:

Carvone is a chemical found naturally in many essential oils and is most abundant in oils from seeds of caraway and spearmint.

Enantiomer is the mirror image of a chemical compound having at least one chiral carbon or chiral centre. Chiral carbon or chiral centre is a carbon atom that is attached to 4 different types of atoms or group of atoms. Enantiomers are also called as the optical isomers.

The enantiomers of carvone are shown below :

        

Step 2:

(a) whether it is the (+) or (-) enantiomer that smells like spearmint?

It is the (-) enantiomer, that smells like spearmint.

Step 3 of 4

Chapter 5, Problem 11P is Solved
Step 4 of 4

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

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If you had the two enantiomers of carvone in unmarked

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