Cholesterol stereogenic centers

Draw the products formed when cholesterol is treated with each reagent. Indicate the stereochemistry around any stereogenic centers in the product. 

One component of lanolin, the wax that coats sheep s wool, is derived from cholesterol and stearic acid. Draw its structure, including the correct stereochemistry at all stereogenic centers. 

Most naturally occurring molecules that contain one stereogenic center exist as one enantiomer. Samples that contain only one enantiomeric form are optically puie. Naturally occurring cholesterol, for example, exists only as the (-) form. It rotates hght in a counterclockwise direction. However, compounds synthesized in the laboratory may not all have the same handedness, and the reaction yields a mixture of two enantiomers. 

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