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Chapter 31: Q19P (page 1257)

Convert the ball-and-stick model of androsterone to (a) a skeletal structure using wedges and dashed wedges around all stereogenic centers; and (b) a three-dimensional representation using chair cyclohexane rings.

androsterone

Short Answer

Expert verified

Answer

(a)

(b)

Step by step solution

01

Androsterone

Androsterone is a natural organic compound with a chemical formula C19H30O2. It contains four cyclic rings (three 6-membered and one 5-membered), one OH group, and one C-O double bond.

At the 17th position, the carbonyl group is present.

02

A skeletal structure of androsterone

(a) The skeletal structure of androsterone is drawn as:

Skeletal structure of androsterone

03

A three-dimensional representation of androsterone using chair cyclohexane rings

(b) The chair cyclohexane rings of androsterone are shown as:

Chair conformation of androsterone

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Most popular questions from this chapter

Question: Flexibilene is a terpene isolated from Sinulariaflexibilis, a soft coral found in the Indian Ocean. Draw a stepwise mechanism for the formation of flexibilene from farnesyl diphosphate and isopentenyl diphosphate. What is unusual about the cyclization that forms the 15-membered ring of flexibilene?

Question: A difficult problem in the synthesis of PGF2ฮฑ is the introduction of the OH group at C15 in the desired configuration.

  1. Label this stereogenic center as R or S.
  2. A well known synthesis of PGF2ฮฑinvolves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.
  3. Suggest a reagent to convert A to the single stereoisomer X.

Draw a stepwise mechanism for the conversion of geranyldiphosphateto ฮฑ-terpinene .

An isoprene unit can be thought of as having a head and a tail. The โ€œheadโ€ of the isoprene unit is located at the end of the chain nearest the branch point, and the โ€œtailโ€ is located at the end of the carbon chain farthest from the branch point. Most isoprene units are connected together in a โ€œhead-to-tailโ€ 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.

(a) Draw a skeletal structure of the anabolic steroid methenolone from the following description. Methenolone contains the tetracyclic steroid skeleton with a carbonyl group at C3, a hydroxyl group at C17, a double bond between C1 and C2, and methyl groups bonded to C1, 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, the configuration at C17 is S, and all substitutents at ring fusions are trans to each other. (c) Draw the structures of Primobolan, the product formed when methenolone is treated with CH3(CH2)5COCl and pyridine. Primobolan is an anabolic steroid that can be taken orally or by injection and has been used illegally by well-known Major League Baseball players.
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