(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.

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Answer 1

Question

Chapter 29, Problem 38P

Interpretation Introduction

(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.

Interpretation Introduction

(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 R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(c)

Interpretation: The structure of Primobolan, the product formed on the treatment of methenolone with CH3(CH2)5COCl and pyridine is to be drawn.

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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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.

Highlight the chirality (or stereogenic) center(s) in the given compound. A compound may have one or more stereogenic centers. OH OH OH OH OH OH

Answer 2

Question

Chapter 29, Problem 38P

Interpretation Introduction

(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.

Interpretation Introduction

(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 R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(c)

Interpretation: The structure of Primobolan, the product formed on the treatment of methenolone with CH3(CH2)5COCl and pyridine is to be drawn.

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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Answer 3

Question

Chapter 29, Problem 38P

Interpretation Introduction

(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.

Interpretation Introduction

(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 R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(c)

Interpretation: The structure of Primobolan, the product formed on the treatment of methenolone with CH3(CH2)5COCl and pyridine is to be drawn.

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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Answer 4

Question

Chapter 29, Problem 38P

Interpretation Introduction

(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.

Interpretation Introduction

(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 R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(c)

Interpretation: The structure of Primobolan, the product formed on the treatment of methenolone with CH3(CH2)5COCl and pyridine is to be drawn.

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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Answer 5

Chapter 29, Problem 38P

Interpretation Introduction

(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.

Interpretation Introduction

(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 R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(c)

Interpretation: The structure of Primobolan, the product formed on the treatment of methenolone with CH3(CH2)5COCl and pyridine is to be drawn.

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.

Answer 6

Chapter 29, Problem 38P

Interpretation Introduction

(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.

Answer 7

Chapter 29, Problem 38P

Interpretation Introduction

(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.

Answer 8

Interpretation Introduction

(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 R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Answer 9

Interpretation Introduction

(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 R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Answer 10

Interpretation Introduction

(c)

Interpretation: The structure of Primobolan, the product formed on the treatment of methenolone with CH3(CH2)5COCl and pyridine is to be drawn.

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.

Answer 11

Interpretation Introduction

(c)

Interpretation: The structure of Primobolan, the product formed on the treatment of methenolone with CH3(CH2)5COCl and pyridine is to be drawn.

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.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 29.2 - Problem 31.1 One component of jojoba oil is a wax...Ch. 29.3 - Problem 31.2 How would you expect the melting...Ch. 29.3 - Problem 31.3 Draw the products formed when...Ch. 29.3 - Problem 31.4 The main fatty acid component of the...Ch. 29.3 - Prob. 5P Ch. 29.7 - Problem 31.10 Locate the isoprene units in each...Ch. 29.7 - Problem 31.11 Locate the isoprene units in...Ch. 29.7 - Problem 31.12 Write a stepwise mechanism for the...Ch. 29.7 - Prob. 14P Ch. 29.8 - Prob. 15P

Solution Summary: The author explains the skeletal structure of the anabolic steroid methenolone from the given description about the configurations at the stereogenic centers.

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Chapter 29 Solutions