Chapter 31: Q15P (page 1253)
Draw the enantiomer and any two diastereomers of cholesterol. Does the OH group of cholesterol occupy an axial or equatorial position?
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Chapter 31: Q15P (page 1253)
Draw the enantiomer and any two diastereomers of cholesterol. Does the OH group of cholesterol occupy an axial or equatorial position?
Answer

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Convert each ball-and-stick model to a skeletal structure that clearly shows the stereochemistry at the ring fusion of these decalin derivatives.
A.

B.

The main fatty acid component of the triacylglycerols in coconut oil is lauric acid, . Explain why coconut oil is a liquid at room temperature even though it contains a large fraction of this saturated fatty acid.
(a) Draw a skeletal structure of the anabolic steroid 4-androstene-3, 17-dione, also called 鈥渁ndro,鈥 from the following description. Andro contains the tetracyclic steroid with carbonyl groups at C3 and C17, a double bond between C4 and C5, and methyl groups bonded to C10 and C13.
(b) Add wedges and dashed wedges for all stereogenic centers with the following information: the configuration at C10 is R, the configuration at C13 is S, and all substituents at ring fusions are trans to each other.
Treatment of cholesterol with mCPBA results in formation of a single epoxide A, with the stereochemistry drawn. Why isn鈥檛 the isomeric epoxide B formed to any extent?

An isoprene unit can be thought of as having a head and a tail. The 鈥渉ead鈥 of the isoprene unit is located at the end of the chain nearest the branch point, and the 鈥渢ail鈥 is located at the end of the carbon chain farthest from the branch point. Most isoprene units are connected together in a 鈥渉ead-to-tail鈥 fashion, as illustrated. For both lycopene (Problem 31.26), and squalene (Figure 31.9), decide which isoprene units are connected in a head-to-tail fashion and which are not.

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