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Solutions_Manual_for_Organic_Chemistry_6th_Ed 195

Solutions_Manual_for_Organic_Chemistry_6th_Ed 195 -...

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8-69 (a) Fumarase catalyzes the addition of H and OH, a hydration reaction. (b) Fumaric acid is planar and cannot be chiral. Malic acid does have a chiral center and is chiral. The enzyme-catalyzed reaction produces only the S enantiomer, so the product must be optically active. (c) One of the fundamental rules of stereochemistry is that optical! y inacti ve starting materials produce optically inactive products. Sulfuric-acid-catalyzed hydration would produce a racemic mixture of malic acid, that is, equal amounts of R and S . (d) If the product is optically active, then either the starting materials or the catalyst were chiral . We know that water and fumaric acid are not chiral, so we must infer that fumarase is chiral. (e) The D and the OD are on the "same side" of the Fischer projection (sometimes called the "erythro"
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