The given substituted acetic acid has to be prepared using malonic ester synthesis. Concept Introduction: Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Question

What are the IUPAC Names of all the compounds in the picture?

Answer 1

Question

Chapter 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(b)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(c)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

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What are the IUPAC Names of all the compounds in the picture?

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

Chapter 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(b)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(c)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

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Answer 3

Question

Chapter 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(b)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(c)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

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Answer 4

Question

Chapter 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(b)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(c)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

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Answer 5

Chapter 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(b)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

(c)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 6

Chapter 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 7

Chapter 19.7, Problem 19.12P

(a)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The given substituted acetic acid has to be prepared using malonic ester synthesis.

Concept Introduction:

Malonic ester is a versatile starting material for the formation of new carbon-carbon bonds. It is because of the presence of acidic α-hydrogens between two carbonyl groups, the nucleophilicity of the enolate anion formed by the loss of α-hydrogen and the ability of the product to undergo decarboxylation after hydrolysis of ester.

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Answer 23

Ch. 19.2 - Prob. 19.1P Ch. 19.2 - Prob. 19.2P Ch. 19.2 - Prob. 19.3P Ch. 19.3 - Prob. 19.4P Ch. 19.3 - Prob. 19.5P Ch. 19.3 - Prob. 19.6P Ch. 19.5 - Prob. 19.7P Ch. 19.5 - Prob. 19.8P Ch. 19.5 - Prob. 19.9P Ch. 19.6 - Prob. 19.10P

Solution Summary: The author explains that malonic ester is a versatile starting material for the formation of new carbon-carbon bonds.

Chapter 19 Solutions