Solutions_Manual_for_Organic_Chemistry_6th_Ed 105

Solutions_Manual_for_Organic_Chemistry_6th_Ed 105 - 5-39(a...

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Unformatted text preview: 5-39 (a) The product has no asymmetric carbon atoms but it has three stereocenters: the carbon with the OH , plus both carbons o f the double bond. Interchange of two bonds on any o f these makes the enantiomer. (b) The product is an example of a chiral compound with no asymmetric carbons. Like the allenes, it is classified as an "extended tetrahedron"; that is, it has four groups that extend from the rigid molecule in four different directions. ( A model will help.) In this structure, the plane containing the COOH and carbons of the double bond is perpendicular to the plane bisecting the OH and H and carbon that they are on. Since the compound is chiral, it is capable of being optically active. COOH H HO H (c) As shown in text Figure 5-16, Section 5-6, catalytic hydrogenation that creates a new chirality center creates a racemic mixture (both enantiomers in a 1: 1 ratio). A racemic mixture is not optically active. In contrast, by using a chiral enzyme to reduce the ketone to the alcohol (as in part (b)), an excess of one enantiomer was produced, so the product was optically active. 98 ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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