The functional groups present in desosamine have to be identified. Concept Introduction: Amide: One − N H 2 , − N H R ' or − N R ' 2 group is attached to the carbonyl carbon atom of the compound. It is represented as R C O N R ' 2 . Amines are the derivatives of ammonia ( N H 3 ) with one or more of the hydrogens replaced with a substituent such as an alkyl group. Depending on the number of carbon side chain of the nitrogen, different types of amines can form. Hemiacetal is an organic compound with a general formula R 1 R 2 C ( O H ) O R where R must be always an alkyl group whereas R 1 and R 2 can be hydrogen or carbon Alcohol: It is an organic compound where it contains at least one − O H group. It is represented as R O H .

Question

(a) Draw a skeletal structure of the anabolic steroid 4-androstene-3,17-dione, also called “andro,” from the following description. Andro contains the tetracyclic steroid skeleton 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.

Answer 1

Question

Chapter 23, Problem 23.22P

(a)

Interpretation Introduction

Interpretation:

The functional groups present in desosamine have to be identified.

Concept Introduction:

Amide: One −NH2, −NHR' or −NR'2 group is attached to the carbonyl carbon atom of the compound. It is represented as RCONR'2.

Amines are the derivatives of ammonia (NH3) with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the nitrogen, different types of amines can form.

Hemiacetal is an organic compound with a general formula R1R2C(OH)OR where R must be always an alkyl group whereas R¹ and R² can be hydrogen or carbon

Alcohol: It is an organic compound where it contains at least one −OH group. It is represented as ROH.

(b)

Interpretation Introduction

Interpretation:

Number of chiral centers are present in desosamine has to be determined. Number of possible stereoisomers for desosamine and the number of enantiomers possible has to be determined.

Concept Introduction:

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

Number of possible stereoisomers for a compound can be determined as,

No of possible stereoisomers = 2nwhere,n = no. of chiral atoms in the compound

Enantiomers: They are chiral molecules whose mirror images are not superimposable.

Number of possible enantiomers for a compound can be determined as,

No of possible stereoisomers = 2n −1 (when n is even)No of possible stereoisomers = 2n −1− 2n/2 −1 (when n is odd)where,n = no. of chiral atoms in the compound

(c)

Interpretation Introduction

Interpretation:

The alternative chair conformations for desosamine have to be drawn.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

(c)

Interpretation Introduction

Interpretation:

More stable alternative chair conformations for desosamine have to be identified and explained.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

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(a) Draw a skeletal structure of the anabolic steroid 4-androstene-3,17-dione, also called “andro,” from the following description. Andro contains the tetracyclic steroid skeleton 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.

Cortisone is a compound that is used as an anti-inflammatory drug to treat 2) diseases like arthritis. Cortisone is a steroid which contains four rings (A, B, C and D), and has the following structure: он "OH Cortisone Provide the data to complete each of the following statements: The total number of chiral carbons (stereocentres) in Cortisone is The maximum number of stereoisomers possible is: The degree of unsaturation (IHD) of Cortisone is The total number of 2° hydrogens is The ring fusion between rings B and C is trans or cis? The absolute configuration of the carbon with * in the structure is The total number of n bonds is

(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 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 thefollowing information: the configuration at C10 is R, the configuration at C13 is S, the configuration at C17 is S, and all substituents at ring fusions are trans to each other. (c) Draw the structure 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.

Answer 2

Question

Chapter 23, Problem 23.22P

(a)

Interpretation Introduction

Interpretation:

The functional groups present in desosamine have to be identified.

Concept Introduction:

Amide: One −NH2, −NHR' or −NR'2 group is attached to the carbonyl carbon atom of the compound. It is represented as RCONR'2.

Amines are the derivatives of ammonia (NH3) with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the nitrogen, different types of amines can form.

Hemiacetal is an organic compound with a general formula R1R2C(OH)OR where R must be always an alkyl group whereas R¹ and R² can be hydrogen or carbon

Alcohol: It is an organic compound where it contains at least one −OH group. It is represented as ROH.

(b)

Interpretation Introduction

Interpretation:

Number of chiral centers are present in desosamine has to be determined. Number of possible stereoisomers for desosamine and the number of enantiomers possible has to be determined.

Concept Introduction:

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

Number of possible stereoisomers for a compound can be determined as,

No of possible stereoisomers = 2nwhere,n = no. of chiral atoms in the compound

Enantiomers: They are chiral molecules whose mirror images are not superimposable.

Number of possible enantiomers for a compound can be determined as,

No of possible stereoisomers = 2n −1 (when n is even)No of possible stereoisomers = 2n −1− 2n/2 −1 (when n is odd)where,n = no. of chiral atoms in the compound

(c)

Interpretation Introduction

Interpretation:

The alternative chair conformations for desosamine have to be drawn.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

(c)

Interpretation Introduction

Interpretation:

More stable alternative chair conformations for desosamine have to be identified and explained.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

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Answer 3

Question

Chapter 23, Problem 23.22P

(a)

Interpretation Introduction

Interpretation:

The functional groups present in desosamine have to be identified.

Concept Introduction:

Amide: One −NH2, −NHR' or −NR'2 group is attached to the carbonyl carbon atom of the compound. It is represented as RCONR'2.

Amines are the derivatives of ammonia (NH3) with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the nitrogen, different types of amines can form.

Hemiacetal is an organic compound with a general formula R1R2C(OH)OR where R must be always an alkyl group whereas R¹ and R² can be hydrogen or carbon

Alcohol: It is an organic compound where it contains at least one −OH group. It is represented as ROH.

(b)

Interpretation Introduction

Interpretation:

Number of chiral centers are present in desosamine has to be determined. Number of possible stereoisomers for desosamine and the number of enantiomers possible has to be determined.

Concept Introduction:

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

Number of possible stereoisomers for a compound can be determined as,

No of possible stereoisomers = 2nwhere,n = no. of chiral atoms in the compound

Enantiomers: They are chiral molecules whose mirror images are not superimposable.

Number of possible enantiomers for a compound can be determined as,

No of possible stereoisomers = 2n −1 (when n is even)No of possible stereoisomers = 2n −1− 2n/2 −1 (when n is odd)where,n = no. of chiral atoms in the compound

(c)

Interpretation Introduction

Interpretation:

The alternative chair conformations for desosamine have to be drawn.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

(c)

Interpretation Introduction

Interpretation:

More stable alternative chair conformations for desosamine have to be identified and explained.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

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Answer 4

Question

Chapter 23, Problem 23.22P

(a)

Interpretation Introduction

Interpretation:

The functional groups present in desosamine have to be identified.

Concept Introduction:

Amide: One −NH2, −NHR' or −NR'2 group is attached to the carbonyl carbon atom of the compound. It is represented as RCONR'2.

Amines are the derivatives of ammonia (NH3) with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the nitrogen, different types of amines can form.

Hemiacetal is an organic compound with a general formula R1R2C(OH)OR where R must be always an alkyl group whereas R¹ and R² can be hydrogen or carbon

Alcohol: It is an organic compound where it contains at least one −OH group. It is represented as ROH.

(b)

Interpretation Introduction

Interpretation:

Number of chiral centers are present in desosamine has to be determined. Number of possible stereoisomers for desosamine and the number of enantiomers possible has to be determined.

Concept Introduction:

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

Number of possible stereoisomers for a compound can be determined as,

No of possible stereoisomers = 2nwhere,n = no. of chiral atoms in the compound

Enantiomers: They are chiral molecules whose mirror images are not superimposable.

Number of possible enantiomers for a compound can be determined as,

No of possible stereoisomers = 2n −1 (when n is even)No of possible stereoisomers = 2n −1− 2n/2 −1 (when n is odd)where,n = no. of chiral atoms in the compound

(c)

Interpretation Introduction

Interpretation:

The alternative chair conformations for desosamine have to be drawn.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

(c)

Interpretation Introduction

Interpretation:

More stable alternative chair conformations for desosamine have to be identified and explained.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

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Answer 5

Chapter 23, Problem 23.22P

(a)

Interpretation Introduction

Interpretation:

The functional groups present in desosamine have to be identified.

Concept Introduction:

Amide: One −NH2, −NHR' or −NR'2 group is attached to the carbonyl carbon atom of the compound. It is represented as RCONR'2.

Amines are the derivatives of ammonia (NH3) with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the nitrogen, different types of amines can form.

Hemiacetal is an organic compound with a general formula R1R2C(OH)OR where R must be always an alkyl group whereas R¹ and R² can be hydrogen or carbon

Alcohol: It is an organic compound where it contains at least one −OH group. It is represented as ROH.

(b)

Interpretation Introduction

Interpretation:

Number of chiral centers are present in desosamine has to be determined. Number of possible stereoisomers for desosamine and the number of enantiomers possible has to be determined.

Concept Introduction:

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

Number of possible stereoisomers for a compound can be determined as,

No of possible stereoisomers = 2nwhere,n = no. of chiral atoms in the compound

Enantiomers: They are chiral molecules whose mirror images are not superimposable.

Number of possible enantiomers for a compound can be determined as,

No of possible stereoisomers = 2n −1 (when n is even)No of possible stereoisomers = 2n −1− 2n/2 −1 (when n is odd)where,n = no. of chiral atoms in the compound

(c)

Interpretation Introduction

Interpretation:

The alternative chair conformations for desosamine have to be drawn.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

(c)

Interpretation Introduction

Interpretation:

More stable alternative chair conformations for desosamine have to be identified and explained.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

Answer 6

Chapter 23, Problem 23.22P

(a)

Interpretation Introduction

Interpretation:

The functional groups present in desosamine have to be identified.

Concept Introduction:

Amide: One −NH2, −NHR' or −NR'2 group is attached to the carbonyl carbon atom of the compound. It is represented as RCONR'2.

Amines are the derivatives of ammonia (NH3) with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the nitrogen, different types of amines can form.

Hemiacetal is an organic compound with a general formula R1R2C(OH)OR where R must be always an alkyl group whereas R¹ and R² can be hydrogen or carbon

Alcohol: It is an organic compound where it contains at least one −OH group. It is represented as ROH.

Answer 7

Chapter 23, Problem 23.22P

(a)

Interpretation Introduction

Interpretation:

The functional groups present in desosamine have to be identified.

Concept Introduction:

Amide: One −NH2, −NHR' or −NR'2 group is attached to the carbonyl carbon atom of the compound. It is represented as RCONR'2.

Amines are the derivatives of ammonia (NH3) with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the nitrogen, different types of amines can form.

Hemiacetal is an organic compound with a general formula R1R2C(OH)OR where R must be always an alkyl group whereas R¹ and R² can be hydrogen or carbon

Alcohol: It is an organic compound where it contains at least one −OH group. It is represented as ROH.

Answer 8

(b)

Interpretation Introduction

Interpretation:

Number of chiral centers are present in desosamine has to be determined. Number of possible stereoisomers for desosamine and the number of enantiomers possible has to be determined.

Concept Introduction:

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

Number of possible stereoisomers for a compound can be determined as,

No of possible stereoisomers = 2nwhere,n = no. of chiral atoms in the compound

Enantiomers: They are chiral molecules whose mirror images are not superimposable.

Number of possible enantiomers for a compound can be determined as,

No of possible stereoisomers = 2n −1 (when n is even)No of possible stereoisomers = 2n −1− 2n/2 −1 (when n is odd)where,n = no. of chiral atoms in the compound

Answer 9

(b)

Interpretation Introduction

Interpretation:

Number of chiral centers are present in desosamine has to be determined. Number of possible stereoisomers for desosamine and the number of enantiomers possible has to be determined.

Concept Introduction:

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

Stereoisomers: Two compounds with same molecular formula but different in their orientation are considered as isomers.

Number of possible stereoisomers for a compound can be determined as,

No of possible stereoisomers = 2nwhere,n = no. of chiral atoms in the compound

Enantiomers: They are chiral molecules whose mirror images are not superimposable.

Number of possible enantiomers for a compound can be determined as,

No of possible stereoisomers = 2n −1 (when n is even)No of possible stereoisomers = 2n −1− 2n/2 −1 (when n is odd)where,n = no. of chiral atoms in the compound

Answer 10

(c)

Interpretation Introduction

Interpretation:

The alternative chair conformations for desosamine have to be drawn.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The alternative chair conformations for desosamine have to be drawn.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

Answer 12

(c)

Interpretation Introduction

Interpretation:

More stable alternative chair conformations for desosamine have to be identified and explained.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

Answer 13

(c)

Interpretation Introduction

Interpretation:

More stable alternative chair conformations for desosamine have to be identified and explained.

Concept Introduction:

Drawing Axial and Equatorial substituents:

Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. The other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.

Answer 14

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Ch. 23.1 - Prob. 23.1P Ch. 23.2 - Prob. 23.2P Ch. 23.2 - Prob. 23.3P Ch. 23.2 - Prob. 23.4P Ch. 23.5 - Prob. 23.5P Ch. 23.5 - Prob. AQ Ch. 23.5 - What is the hybridization of the nitrogen in...Ch. 23.5 - Prob. CQ Ch. 23.5 - The pKas of the conjugate acids of aniline and...Ch. 23.5 - Prob. EQ

Solution Summary: The author explains the functional groups present in desosamine. Amides are the derivatives of ammonia with one or more hydrogens replaced with a substituent.

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Chapter 23 Solutions