To describe how the given compound can be prepared from diethyl malonate and other reagents. Concept introduction: Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below, Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis) Steps involved in malonic ester synthesis are, Deprotonation of α carbon in malonic acid ester Alkylation of enolate Hydrolysis of ester using aqueous acid Decarboxylation at high temperature

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Answer 1

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 21, Problem 68PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

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1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following compounds. Please show your work. (8) SF2, CH,OH, C₂H₂ b) Based on your answers given above, list the compounds in order of their Boiling Point from low to high. (8)

19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 21, Problem 68PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 21, Problem 68PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 21, Problem 68PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 21, Problem 68PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 6

Chapter 21, Problem 68PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 7

Chapter 21, Problem 68PP

(a)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 8

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 9

(b)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 10

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 11

(c)

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared from diethyl malonate and other reagents.

Concept introduction:

Malonic ester synthesis is a process in which an halide is converted to a carboxylic acid with two new carbon atoms (comes from malonic ester). By use of this method two new alkyl groups can be introduced. A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for malonic ester synthesis a cyclic product is expected. (Intramolecular malonic ester synthesis)

Steps involved in malonic ester synthesis are,

Deprotonation of α carbon in malonic acid ester

Alkylation of enolate

Hydrolysis of ester using aqueous acid

Decarboxylation at high temperature

Answer 12

Expert Solution & Answer

Answer 13

Expert Solution & Answer

Answer 14

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Answer 15

Ch. 21.1 - Prob. 1CC Ch. 21.1 - Prob. 2CC Ch. 21.1 - Prob. 3CC Ch. 21.1 - Prob. 1LTS Ch. 21.1 - Prob. 4PTS Ch. 21.1 - Prob. 5ATS Ch. 21.1 - Prob. 6CC Ch. 21.1 - Prob. 7CC Ch. 21.2 - Prob. 8CC Ch. 21.2 - Prob. 9CC

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Chapter 21 Solutions