a) Interpretation: The products of the reaction shown are to be given. Concept introduction: Ethers are cleaved by strong acids. The cleavage takes place either by S N 1 or S N 2 mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S N 2 mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide . Ethers with a tertiary, benzylic or an allylic group cleave either by S N 1 or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols. To give: The products of the reaction shown.

Question

A small artisanal cheesemaker is testing the acidity of their milk before it coagulates. During fermentation, bacteria produce lactic acid (K₁ = 1.4 x 104), a weak acid that helps to curdle the milk and develop flavor. The cheesemaker has measured that the developing mixture contains lactic acid at an initial concentration of 0.025 M. Your task is to calculate the pH of this mixture and determine whether it meets the required acidity for proper cheese development. To achieve the best flavor, texture and reduce/control microbial growth, the pH range needs to be between pH 4.6 and 5.0. Assumptions: Lactic acid is a monoprotic acid H H :0:0: H-C-C H :0: O-H Figure 1: Lewis Structure for Lactic Acid For simplicity, you can use the generic formula HA to represent the acid You can assume lactic acid dissociation is in water as milk is mostly water. Temperature is 25°C 1. Write the K, expression for the dissociation of lactic acid in the space provided. Do not forget to include state symbols.…

Answer 1

Question

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

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A small artisanal cheesemaker is testing the acidity of their milk before it coagulates. During fermentation, bacteria produce lactic acid (K₁ = 1.4 x 104), a weak acid that helps to curdle the milk and develop flavor. The cheesemaker has measured that the developing mixture contains lactic acid at an initial concentration of 0.025 M. Your task is to calculate the pH of this mixture and determine whether it meets the required acidity for proper cheese development. To achieve the best flavor, texture and reduce/control microbial growth, the pH range needs to be between pH 4.6 and 5.0. Assumptions: Lactic acid is a monoprotic acid H H :0:0: H-C-C H :0: O-H Figure 1: Lewis Structure for Lactic Acid For simplicity, you can use the generic formula HA to represent the acid You can assume lactic acid dissociation is in water as milk is mostly water. Temperature is 25°C 1. Write the K, expression for the dissociation of lactic acid in the space provided. Do not forget to include state symbols.…

Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. :0: :0 H. 0:0 :0: :6: S: :0: Select to Edit Arrows ::0 Select to Edit Arrows H :0: H :CI: Rotation Select to Edit Arrows H. < :0: :0: :0: S:

3:48 PM Fri Apr 4 K Problem 4 of 10 Submit Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. Mg. :0: Select to Add Arrows :0: :Br: Mg :0: :0: Select to Add Arrows Mg. Br: :0: 0:0- Br -190 H 0:0 Select to Add Arrows Select to Add Arrows neutralizing workup H CH3

Answer 2

Question

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

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Answer 3

Question

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

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Answer 4

Question

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

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Answer 5

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

Answer 6

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Answer 7

Chapter 18.SE, Problem 56GP

Interpretation Introduction

a)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by S_N¹ or S_N² mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by S_N² mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by S_N¹ or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The products of the reaction shown.

Answer 8

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Answer 9

Interpretation Introduction

b)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Treatment of an alkyl halide with thiourea gives alkyl thiourea salt. The salt when hydrolyzed with aqueous bases yields the thiol. The alkyl bromide can be prepared by treating an alcohol with PBr₃.

To give:

The product of the reaction shown.

Answer 10

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Answer 11

Interpretation Introduction

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

Answer 12

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

Answer 13

Interpretation Introduction

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

Answer 14

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Answer 15

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Answer 25

Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6P Ch. 18.3 - Prob. 7P Ch. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...

Solution Summary: The author explains that the products of the reaction shown are phenol and 1-bromo-2-methylpropane.

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.

Chapter 18 Solutions

Solution Summary: The author explains that the products of the reaction shown are phenol and 1-bromo-2-methylpropane.

c) Interpretation: The products of the reaction shown are to be given. Concept introduction: Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature. To give: The product of the reaction shown.

d) Interpretation: The products of the reaction shown are to be given. Concept introduction: Sulfides in general are easily oxidized. When treated with H2O2 at room temperature they are oxidized to the corresponding sulfoxides. To give: The product of the reaction shown.

Chapter 18 Solutions

c)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Bromine and iodine oxidize thiols to disulfides. The reaction is reversible in nature.

To give:

The product of the reaction shown.

d)

Interpretation:

The products of the reaction shown are to be given.

Concept introduction:

Sulfides in general are easily oxidized. When treated with H₂O₂ at room temperature they are oxidized to the corresponding sulfoxides.

To give:

The product of the reaction shown.