(a) Interpretation: Each double bond in lejimalide B is to be labeled as E or Z . Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. The use of prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is an Z isomer. The priority order depends upon the atomic number of the elements.

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Answer 1

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Chapter 10, Problem 10.46P

Interpretation Introduction

(a)

Interpretation: Each double bond in lejimalide B is to be labeled as E or Z.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions.

The use of prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is an Z isomer. The priority order depends upon the atomic number of the elements.

Interpretation Introduction

(b)

Interpretation: Each tetrahedral stereogenic center in the given drug is to be labeled as R or S.

Concept introduction: Rules for assigning R and S configuration are as follows:

1. The groups are prioritized on the basis of their atomic numbers. Atom with highest atomic number is assigned the first position.

2. If the atoms that are attached to the chiral centre are similar to each other, then the priority is given on the basis of the next atom attached.

3. The molecule is oriented in such a manner that the lowest priority group comes at the dashed wedge.

4. If the first three high priority groups are present in a clockwise manner then the molecule is assigned R configuration but if these are present in an anticlockwise manner then the molecule is assigned with S configuration.

Interpretation Introduction

(c)

Interpretation: The number of stereoisomers possible for lejimalide B is to be predicted.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termed as chiral center or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers. A pair of diastereomers exists when two substituents attached to each of the double bonded carbon atoms are different.

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lejimalide B, an anticancer agent with a 24-membered ring, is isolated from a tunicate found off le Island in Okinawa. (a) Label each double bond in iejimalide B as E or Z. (b) Label each tetrahedral stereogenic center as R or S. (c) How many stereoisomers are possible for iejimalide B? CH;0 CHO OCH, HO, iejimalide B

Attenol A and pinnatoxin A are natural products isolated from marine sources. (a) Locate the acetals, hemiacetals, imines, and enamines in both compounds. (b) Draw the hydrolysis product formed when attenol A is treated with aqueous acid. Include stereochemistry at all stereogenic centers.

Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?

Answer 2

Question

Chapter 10, Problem 10.46P

Interpretation Introduction

(a)

Interpretation: Each double bond in lejimalide B is to be labeled as E or Z.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions.

The use of prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is an Z isomer. The priority order depends upon the atomic number of the elements.

Interpretation Introduction

(b)

Interpretation: Each tetrahedral stereogenic center in the given drug is to be labeled as R or S.

Concept introduction: Rules for assigning R and S configuration are as follows:

1. The groups are prioritized on the basis of their atomic numbers. Atom with highest atomic number is assigned the first position.

2. If the atoms that are attached to the chiral centre are similar to each other, then the priority is given on the basis of the next atom attached.

3. The molecule is oriented in such a manner that the lowest priority group comes at the dashed wedge.

4. If the first three high priority groups are present in a clockwise manner then the molecule is assigned R configuration but if these are present in an anticlockwise manner then the molecule is assigned with S configuration.

Interpretation Introduction

(c)

Interpretation: The number of stereoisomers possible for lejimalide B is to be predicted.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termed as chiral center or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers. A pair of diastereomers exists when two substituents attached to each of the double bonded carbon atoms are different.

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Answer 3

Question

Chapter 10, Problem 10.46P

Interpretation Introduction

(a)

Interpretation: Each double bond in lejimalide B is to be labeled as E or Z.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions.

The use of prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is an Z isomer. The priority order depends upon the atomic number of the elements.

Interpretation Introduction

(b)

Interpretation: Each tetrahedral stereogenic center in the given drug is to be labeled as R or S.

Concept introduction: Rules for assigning R and S configuration are as follows:

1. The groups are prioritized on the basis of their atomic numbers. Atom with highest atomic number is assigned the first position.

2. If the atoms that are attached to the chiral centre are similar to each other, then the priority is given on the basis of the next atom attached.

3. The molecule is oriented in such a manner that the lowest priority group comes at the dashed wedge.

4. If the first three high priority groups are present in a clockwise manner then the molecule is assigned R configuration but if these are present in an anticlockwise manner then the molecule is assigned with S configuration.

Interpretation Introduction

(c)

Interpretation: The number of stereoisomers possible for lejimalide B is to be predicted.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termed as chiral center or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers. A pair of diastereomers exists when two substituents attached to each of the double bonded carbon atoms are different.

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Answer 4

Question

Chapter 10, Problem 10.46P

Interpretation Introduction

(a)

Interpretation: Each double bond in lejimalide B is to be labeled as E or Z.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions.

The use of prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is an Z isomer. The priority order depends upon the atomic number of the elements.

Interpretation Introduction

(b)

Interpretation: Each tetrahedral stereogenic center in the given drug is to be labeled as R or S.

Concept introduction: Rules for assigning R and S configuration are as follows:

1. The groups are prioritized on the basis of their atomic numbers. Atom with highest atomic number is assigned the first position.

2. If the atoms that are attached to the chiral centre are similar to each other, then the priority is given on the basis of the next atom attached.

3. The molecule is oriented in such a manner that the lowest priority group comes at the dashed wedge.

4. If the first three high priority groups are present in a clockwise manner then the molecule is assigned R configuration but if these are present in an anticlockwise manner then the molecule is assigned with S configuration.

Interpretation Introduction

(c)

Interpretation: The number of stereoisomers possible for lejimalide B is to be predicted.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termed as chiral center or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers. A pair of diastereomers exists when two substituents attached to each of the double bonded carbon atoms are different.

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Answer 5

Chapter 10, Problem 10.46P

Interpretation Introduction

(a)

Interpretation: Each double bond in lejimalide B is to be labeled as E or Z.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions.

The use of prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is an Z isomer. The priority order depends upon the atomic number of the elements.

Interpretation Introduction

(b)

Interpretation: Each tetrahedral stereogenic center in the given drug is to be labeled as R or S.

Concept introduction: Rules for assigning R and S configuration are as follows:

1. The groups are prioritized on the basis of their atomic numbers. Atom with highest atomic number is assigned the first position.

2. If the atoms that are attached to the chiral centre are similar to each other, then the priority is given on the basis of the next atom attached.

3. The molecule is oriented in such a manner that the lowest priority group comes at the dashed wedge.

4. If the first three high priority groups are present in a clockwise manner then the molecule is assigned R configuration but if these are present in an anticlockwise manner then the molecule is assigned with S configuration.

Interpretation Introduction

(c)

Interpretation: The number of stereoisomers possible for lejimalide B is to be predicted.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termed as chiral center or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers. A pair of diastereomers exists when two substituents attached to each of the double bonded carbon atoms are different.

Answer 6

Chapter 10, Problem 10.46P

Interpretation Introduction

(a)

Interpretation: Each double bond in lejimalide B is to be labeled as E or Z.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions.

The use of prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is an Z isomer. The priority order depends upon the atomic number of the elements.

Answer 7

Chapter 10, Problem 10.46P

Interpretation Introduction

(a)

Interpretation: Each double bond in lejimalide B is to be labeled as E or Z.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions.

The use of prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is an Z isomer. The priority order depends upon the atomic number of the elements.

Answer 8

Interpretation Introduction

(b)

Interpretation: Each tetrahedral stereogenic center in the given drug is to be labeled as R or S.

Concept introduction: Rules for assigning R and S configuration are as follows:

1. The groups are prioritized on the basis of their atomic numbers. Atom with highest atomic number is assigned the first position.

2. If the atoms that are attached to the chiral centre are similar to each other, then the priority is given on the basis of the next atom attached.

3. The molecule is oriented in such a manner that the lowest priority group comes at the dashed wedge.

4. If the first three high priority groups are present in a clockwise manner then the molecule is assigned R configuration but if these are present in an anticlockwise manner then the molecule is assigned with S configuration.

Answer 9

Interpretation Introduction

(b)

Interpretation: Each tetrahedral stereogenic center in the given drug is to be labeled as R or S.

Concept introduction: Rules for assigning R and S configuration are as follows:

1. The groups are prioritized on the basis of their atomic numbers. Atom with highest atomic number is assigned the first position.

2. If the atoms that are attached to the chiral centre are similar to each other, then the priority is given on the basis of the next atom attached.

3. The molecule is oriented in such a manner that the lowest priority group comes at the dashed wedge.

4. If the first three high priority groups are present in a clockwise manner then the molecule is assigned R configuration but if these are present in an anticlockwise manner then the molecule is assigned with S configuration.

Answer 10

Interpretation Introduction

(c)

Interpretation: The number of stereoisomers possible for lejimalide B is to be predicted.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termed as chiral center or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers. A pair of diastereomers exists when two substituents attached to each of the double bonded carbon atoms are different.

Answer 11

Interpretation Introduction

(c)

Interpretation: The number of stereoisomers possible for lejimalide B is to be predicted.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termed as chiral center or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers. A pair of diastereomers exists when two substituents attached to each of the double bonded carbon atoms are different.

Answer 12

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Answer 13

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Answer 15

Ch. 10 - Prob. 10.1P Ch. 10 - Problem 10.2 How many degrees of unsaturation are...Ch. 10 - Give an example of a compound with molecular...Ch. 10 - Give the IUPAC name for each alkene.Ch. 10 - Give the IUPAC name for each polyfunctional...Ch. 10 - Prob. 10.6P Ch. 10 - Prob. 10.7P Ch. 10 - Prob. 10.8P Ch. 10 - Prob. 10.9P Ch. 10 - Problem 10.10 Rank the following isomers in order...

Solution Summary: The author explains that each double bond in lejimalide B is to be labeled as E or Z.

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