Apiose is one of several naturally occurring carbohydrates characterized by a branched

Chapter 13, Problem 13.56

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Apiose is one of several naturally occurring carbohydrates characterized by a branched carbon chain and is conveniently isolated as the compound shown (diacetone apiose). Based on the observation that the protons at C(1) and C(2) have a coupling constant of 3.7 Hz, choose the correct statement. O O O H H O O 1 2 Diacetone apiose (a) The C(1) and C(2) protons are eclipsed. (b) The H C(1) C(2) H dihedral angle is in the range 3060. (c) The H C(1) C(2) H dihedral angle is in the range 145165 (d) The C(1) and C(2) protons are anti.

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