Chapter 3: Problem 7
How many stereoisomers exist for 1,3 -cyclopentanediol?
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For centuries, Chinese herbal medicine has used extracts of Ephedra sinica to treat asthma. Ephedra as an "herbal supplement" has been implicated in the deaths of several athletes and has recently been banned as a dietary supplement. Phytochemical investigation of this plant resulted in isolation of ephedrine, a very potent dilator of the air passages of the lungs. Ephedrine also has profound effects on the cardiovascular system. The naturally occurring stereoisomer is levorotatory and has the following structure. Assign an \(R\) or \(S\) configuration to each chiral center.
Assign priorities to the groups in each set. (a) \(-\mathrm{CH}_{2} \mathrm{OH}\) and \(-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(-\mathrm{CH}_{2} \mathrm{OH}\) and \(-\mathrm{CH}=\mathrm{CH}_{2}\) (c) \(-\mathrm{CH}_{2} \mathrm{OH}\) and \(-\mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\)
How many stereoisomers exist for 1,4 -cyclohexanediol?
Which compounds contain chiral centers? (a) 2-Chloropentane (b) 3-Chloropentane (c) 3-Chloro-l-pentene (d) 1,2-Dichloropropane
To the following statements, answer true or false and explain your answer. (a) All chiral centers are also stereocenters. (b) All stereocenters are also chiral centers. (c) All chiral molecules are optically active when pure. (d) All mixtures of chiral molecules are optically active. (e) To be optically active, a molecule must have a chiral center. (f) To be meso, a molecule must have at least two chiral centers.
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