EBK ORGANIC CHEMISTRY-PRINT COMPANION (
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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Alkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.
(a) Locate the isoprene units in lycopene, the red pigment in tomatoes. (b) Which isoprene units are connected in a head-to-tail fashion? (c) Label any other isoprene unit as connected in a head-tohead fashion or a tail-to-tail fashion. (d) Classify lycopene as a monoterpene, sesquiterpene, and so on.
Draw the organic products formed when attached compound is treated with H2, Pd-C. Indicate the three-dimensional structure of all stereoisomersformed.
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