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(a)
Interpretation: The skeletal structure of the anabolic steroid methenolone from the given description is to be drawn.
Concept introduction: Steroids are composed of tetracyclic lipids. They have structure containing three six membered ring and one five membered ring. Some of the steroids are biologically active.
(b)
Interpretation: The skeletal structure of the anabolic steroid methenolone from the given description about the configurations at the stereogenic centers is to be drawn.
Concept introduction: Steroids are composed of tetracyclic lipids. They have structure containing three six membered ring and one five membered ring. Some of the steroids are biologically active.
The stereogenic centers with
(c)
Interpretation: The structure of Primobolan, the product formed on the treatment of methenolone with
Concept introduction: In the presence of base, the hydroxyl group loses its proton to form alkoxide. The alkoxide attacks on the carbonyl carbon of acyl chloride or acylic anhydride to leading to the formation of acyl group and removal of chloride. This process is known as acylation.
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Chapter 29 Solutions
ORGANIC CHEMISTRY-ACCESS
- (v) Identify every chiral center in cholesterol (below) with an asterisk. HO (vi) Draw an energy vs. dihedral angle diagram that represents all the conformations of butane starting from the anti-conformation. (vii) Draw both chair conformations for the compound shown below using the templates provided. Circle the chair conformation that is lowest in energy. Br (viii) Draw a chair conformation that meets the following criteria. Axial chlorine at C5 Equatorial methyl at C4 Bromine on C2 that is cis to the chlorine 6 2 5 3 4arrow_forward(b) Identify the carbon atoms in the following molecules as primary (1°), secondary (2°), tertiary (3°), or quaternary (4°). (a) CH3 (Б) CH3CHCH3 (c) CH3 CH3 CH3CHCH2CH2CH3 CH3CH2CHCH2CH3 CH3CHCH2CCH3 CH3arrow_forward1) Identify the number of hydrogens implicitly attached to the five specified carbons in this bond-line structure of cholesterol. 2) Identify (circle and name) all of the functional groups in the following structure of serotonin.arrow_forward
- 4. (a) Draw a skeletal (line-bond) structure for 3,4-dimethylhexane. (b) Draw a sawhorse representation of any staggered conformation of this molecule looking down the carbon-3 to carbon-4 bond. (c) Draw a Newman projection looking down the carbon-3 to carbon-4 bond of the same conformation that you drew as a sawhorse representation.arrow_forward1) Below you are given the structures of the disaccharides lactose and trehalose. он он но он но но OH но но OH но он но но OH Lactose Trehalose a. Identify clearly the hemiacetal and acetal groups in these disaccharides and determine for each of these identified groups if they have a- or B-configuration.arrow_forward(b) Classify the following two pairs of structures as conformational or configurational isomers. Explain your answer. and HO, OH il. and ноarrow_forward
- 31. Which of the following statements about cholesterol is not correct? CH. HO Cholesterol 16 (a) Cholesterol is a steroid that contains a tetracyclic ring system. (b) Cholesterol is a steroid that contains 8 chiral carbons and can form 28 or 256 stereoisomers. (c) Each atom or group attached to a ring-junction carbon (i.e., carbons a-e) is in a trans or axial position. Because of this the tetracyclic ring system is mostly flat. (d) Cholesterol is used to synthesized vitamin D, bile acids, sex hormones, and adrenocorticoid hormones. (e) Cholesterol is not found in the cell membranes of animals.arrow_forwardCalculate the degree of unsaturation in each of the following formulas (a) Cholesterol, C27H46o (b) DDT, C14HgC15 (c) Prostaglandin E1, C2oH3405 (d) Caffeine, C8H10N402 (e) Cortisone, C21H28O5 (f) Atropine, C17H23NO3arrow_forward(9) How many chiral centers are present in a molecule of 1,3-dimethylcyclohexane? (C) 2 (D) 3 1 (A) O (10) What is the percent composition of a mixture of (S)-(+)-2-butanol, [a] = +13.52°, and (R)-(-)-2-butanol, [a] = -13.52°, with a specific rotation [a]D = -6.76° (A) 75%R 25%S (B) 25%R 75%S (C) 50%R 50%S 67%R 33%Sarrow_forward
- An amide is typically drawn with a single bond connecting the carbonyl C atom to the N atom. If this representation were accurate, we would expect the N atom to be pyramidal, and we would also expect C-N to undergo free rotation. In actuality, however, the N atom is rather planar, and the rotation is quite hindered-properties that give rise to important secondary structures of proteins, such as a helices and B sheets (Chapter 26). Explain these properties of the amide. R `NH2 An amidearrow_forward(a) Identify type of molecules either chiral, achiral, or meso for each compound shown below and (b) Indicate the number of chiral centers in each molecule.arrow_forwardCoibacin B (shown below) is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites (Org. Lett. 2012, 14, 3878-3881): (a) Assign the configuration (R or S) of each chirality center (labeled A to C) in coibacin B. (b) Identify the number of possible stereoisomers for this compound, assuming that the geometry of the alkenes are fixed. Choices are given below and write the CAPITAL LETTER of your choice. A. 2 В. 4 С. 8 D. 16 ANSWERS: (a) A. В. C. (b)arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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