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12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the 1R,2S,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S,2R,5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15,2S,5R-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?

12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the 1R,2S,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S,2R,5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15,2S,5R-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the 1R,2S,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S,2R,5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15,2S,5R-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?
Transcribed Image Text:12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the 1R,2S,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S,2R,5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15,2S,5R-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?
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