1,1'-Bi-2-naphthol is a chiral compound, and its enantiomers can be separated from each other. The enantiomer shown here has a specific rotation of -32.70° in tetrahydrofuran. (Notice that the two fused-ring systems are not in the same plane. In the top ring system, the left side is in front of the plane of the page, whereas in the bottom ring system, the right side is in front.) "OH OH 1,1'-Bi-2-naphthol (a) How many chiral centers does 1,1'-bi-2-naphthol have? (b) Draw the enantiomer of the molecule shown. What is its specific rotation? (c) Aside from being mirror images of each other, how else are the two enantiomers related? Why do you think they do not readily interconvert? Hint: It may help to construct a molecular model.

1,1'-Bi-2-naphthol is a chiral compound, and its enantiomers can be separated from each other. The enantiomer shown here has a specific rotation of -32.70° in tetrahydrofuran. (Notice that the two fused-ring systems are not in the same plane. In the top ring system, the left side is in front of the plane of the page, whereas in the bottom ring system, the right side is in front.) "OH OH 1,1'-Bi-2-naphthol (a) How many chiral centers does 1,1'-bi-2-naphthol have? (b) Draw the enantiomer of the molecule shown. What is its specific rotation? (c) Aside from being mirror images of each other, how else are the two enantiomers related? Why do you think they do not readily interconvert? Hint: It may help to construct a molecular model.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter12: Chirality

Section: Chapter Questions

Problem 11CTQ

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1,1'-Bi-2-naphthol is a chiral compound, and its enantiomers can be separated from each other. The enantiomer shown here has a specific rotation of – 32.70° in tetrahydrofuran. (Notice that the two fused-ring systems are not in the same plane. In the top ring system, the left side is in front of the plane of the page, whereas in the bottom ring system, the right side is in front.) HO, OH 1,1'-Bi-2-naphthol (a) How many chiral centers does 1,1'-bi-2-naphthol have? (b) Draw the enantiomer of the molecule shown. What is its specific rotation? (c) Aside from being mirror images of each other, how else are the two enantiomers related? Why do you think they do not readily interconvert? Hint: It may help to construct a molecular model.
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