(a) Interpretation: The stereogenic center(s) is to be labeled. Concept introduction: Stereoisomers are the compounds in which molecular formula of a compound remains same but positions of different atoms or groups are changed to form new compounds. The stereogenic centers are also known as sterocenters. The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers.

Question

Etoposide, sold as a phosphate derivative with the trade name of Etopophos, is used for the treatment of lung cancer, testicular cancer, and lymphomas. (a) Locate the acetals in etoposide. (b) What products are formed when all of the acetals are hydrolyzed with aqueous acid?

Answer 1

Question

Chapter 25, Problem 25.64P

Interpretation Introduction

(a)

Interpretation: The stereogenic center(s) is to be labeled.

Concept introduction: Stereoisomers are the compounds in which molecular formula of a compound remains same but positions of different atoms or groups are changed to form new compounds. The stereogenic centers are also known as sterocenters. The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers.

Interpretation Introduction

(b)

Interpretation: Amide(s) that can be reduced to form benzphetamine is to be predicted.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Interpretation Introduction

(c)

Interpretation: The carbonyl compound and amine that can be used to make benzphetamine by reductive amination are to be stated. The possible methods are to be drawn.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Interpretation Introduction

(d)

Interpretation: The products which are formed by Hofmann elimination from benzphetamine are to be drawn. The major product is to be labeled.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. Hoffman’s elimination reaction involves the less substituted alkene as a more favourable product, whereas according to Zaitsev rule, more substituted alkenes are considered as the more favourable product.

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Etoposide, sold as a phosphate derivative with the trade name of Etopophos, is used for the treatment of lung cancer, testicular cancer, and lymphomas. (a) Locate the acetals in etoposide. (b) What products are formed when all of the acetals are hydrolyzed with aqueous acid?

The following compounds are named incorrectly. Draw the structure of each compound and give it a correct name (either IUPAC or common is acceptable.) a) N-phenyl-N-ethyl-2-propanamine b) N-sec-butyl-N-propylmethanamine c) N-methyl-N-ethyl-4-ethylpentanamide d) 2,5-diethylhexanoic acid f Googlo Chegg Course Hero or

Answer the following questions about benzphetamine, a habit-forming diet pill sold under the trade name Didrex. a. Label the stereogenic center(s). b. What amide(s) can be reduced to form benzphetamine? c. What carbonyl compound and amine can be used to make benzphetamine by reductive amination? Draw all possible methods. d. What products are formed by Hofmann elimination from benzphetamine? Label the major product. benzphetamine

Answer 2

Question

Chapter 25, Problem 25.64P

Interpretation Introduction

(a)

Interpretation: The stereogenic center(s) is to be labeled.

Concept introduction: Stereoisomers are the compounds in which molecular formula of a compound remains same but positions of different atoms or groups are changed to form new compounds. The stereogenic centers are also known as sterocenters. The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers.

Interpretation Introduction

(b)

Interpretation: Amide(s) that can be reduced to form benzphetamine is to be predicted.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Interpretation Introduction

(c)

Interpretation: The carbonyl compound and amine that can be used to make benzphetamine by reductive amination are to be stated. The possible methods are to be drawn.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Interpretation Introduction

(d)

Interpretation: The products which are formed by Hofmann elimination from benzphetamine are to be drawn. The major product is to be labeled.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. Hoffman’s elimination reaction involves the less substituted alkene as a more favourable product, whereas according to Zaitsev rule, more substituted alkenes are considered as the more favourable product.

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Answer 3

Question

Chapter 25, Problem 25.64P

Interpretation Introduction

(a)

Interpretation: The stereogenic center(s) is to be labeled.

Concept introduction: Stereoisomers are the compounds in which molecular formula of a compound remains same but positions of different atoms or groups are changed to form new compounds. The stereogenic centers are also known as sterocenters. The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers.

Interpretation Introduction

(b)

Interpretation: Amide(s) that can be reduced to form benzphetamine is to be predicted.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Interpretation Introduction

(c)

Interpretation: The carbonyl compound and amine that can be used to make benzphetamine by reductive amination are to be stated. The possible methods are to be drawn.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Interpretation Introduction

(d)

Interpretation: The products which are formed by Hofmann elimination from benzphetamine are to be drawn. The major product is to be labeled.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. Hoffman’s elimination reaction involves the less substituted alkene as a more favourable product, whereas according to Zaitsev rule, more substituted alkenes are considered as the more favourable product.

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Answer 4

Question

Chapter 25, Problem 25.64P

Interpretation Introduction

(a)

Interpretation: The stereogenic center(s) is to be labeled.

Concept introduction: Stereoisomers are the compounds in which molecular formula of a compound remains same but positions of different atoms or groups are changed to form new compounds. The stereogenic centers are also known as sterocenters. The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers.

Interpretation Introduction

(b)

Interpretation: Amide(s) that can be reduced to form benzphetamine is to be predicted.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Interpretation Introduction

(c)

Interpretation: The carbonyl compound and amine that can be used to make benzphetamine by reductive amination are to be stated. The possible methods are to be drawn.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Interpretation Introduction

(d)

Interpretation: The products which are formed by Hofmann elimination from benzphetamine are to be drawn. The major product is to be labeled.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. Hoffman’s elimination reaction involves the less substituted alkene as a more favourable product, whereas according to Zaitsev rule, more substituted alkenes are considered as the more favourable product.

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Answer 5

Chapter 25, Problem 25.64P

Interpretation Introduction

(a)

Interpretation: The stereogenic center(s) is to be labeled.

Concept introduction: Stereoisomers are the compounds in which molecular formula of a compound remains same but positions of different atoms or groups are changed to form new compounds. The stereogenic centers are also known as sterocenters. The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers.

Interpretation Introduction

(b)

Interpretation: Amide(s) that can be reduced to form benzphetamine is to be predicted.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Interpretation Introduction

(c)

Interpretation: The carbonyl compound and amine that can be used to make benzphetamine by reductive amination are to be stated. The possible methods are to be drawn.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Interpretation Introduction

(d)

Interpretation: The products which are formed by Hofmann elimination from benzphetamine are to be drawn. The major product is to be labeled.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. Hoffman’s elimination reaction involves the less substituted alkene as a more favourable product, whereas according to Zaitsev rule, more substituted alkenes are considered as the more favourable product.

Answer 6

Chapter 25, Problem 25.64P

Interpretation Introduction

(a)

Interpretation: The stereogenic center(s) is to be labeled.

Concept introduction: Stereoisomers are the compounds in which molecular formula of a compound remains same but positions of different atoms or groups are changed to form new compounds. The stereogenic centers are also known as sterocenters. The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers.

Answer 7

Chapter 25, Problem 25.64P

Interpretation Introduction

(a)

Interpretation: The stereogenic center(s) is to be labeled.

Concept introduction: Stereoisomers are the compounds in which molecular formula of a compound remains same but positions of different atoms or groups are changed to form new compounds. The stereogenic centers are also known as sterocenters. The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers.

Answer 8

Interpretation Introduction

(b)

Interpretation: Amide(s) that can be reduced to form benzphetamine is to be predicted.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer 9

Interpretation Introduction

(b)

Interpretation: Amide(s) that can be reduced to form benzphetamine is to be predicted.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer 10

Interpretation Introduction

(c)

Interpretation: The carbonyl compound and amine that can be used to make benzphetamine by reductive amination are to be stated. The possible methods are to be drawn.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer 11

Interpretation Introduction

(c)

Interpretation: The carbonyl compound and amine that can be used to make benzphetamine by reductive amination are to be stated. The possible methods are to be drawn.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. The synthesis of the products relies upon the type of reactants and reagents that are used during the reactions. The energy of a target molecule should be low because it increases the stability of a molecule that results in the formation of molecules with high yield. The reagents perform numerous functions in reactions like proton abstraction, oxidation, reduction, catalysis, and dehydrogenation.

Answer 12

Interpretation Introduction

(d)

Interpretation: The products which are formed by Hofmann elimination from benzphetamine are to be drawn. The major product is to be labeled.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. Hoffman’s elimination reaction involves the less substituted alkene as a more favourable product, whereas according to Zaitsev rule, more substituted alkenes are considered as the more favourable product.

Answer 13

Interpretation Introduction

(d)

Interpretation: The products which are formed by Hofmann elimination from benzphetamine are to be drawn. The major product is to be labeled.

Concept introduction: Amines are the derivatives of ammonia consisting of nitrogen atom with the lone pair of electrons. They are basic compounds. Hoffman’s elimination reaction involves the less substituted alkene as a more favourable product, whereas according to Zaitsev rule, more substituted alkenes are considered as the more favourable product.

Answer 14

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Answer 25

Ch. 25 - Prob. 25.1P Ch. 25 - Draw the structure of a compound of molecular...Ch. 25 - Prob. 25.3P Ch. 25 - Prob. 25.4P Ch. 25 - Prob. 25.5P Ch. 25 - Arrange the compounds in order of increasing...Ch. 25 - Prob. 25.7P Ch. 25 - Prob. 25.8P Ch. 25 - Problem 25.7 Draw the product of each...Ch. 25 - Prob. 25.10P

Solution Summary: The author explains the stereogenic center(s) in the given compound, which is labeled in figure 1.

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Chapter 25 Solutions