a) Interpretation: A structure for methyl orange, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown. Concept introduction: The diazonium cation can act as an electrophile and can attack aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction. To draw: The structure of methyl orange, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Question

This organic molecule is dissolved in an acidic aqueous solution: OH OH A short time later sensitive infrared spectroscopy reveals the presence of a new C = O stretch absorption. That is, there must now be a new molecule present with at least one C = O bond. In the drawing area below, show the detailed mechanism that could convert the molecule above into the new molecule. Videos 849 Explanation Check C Click and drag to start dwing a structure. # 3 MAR 23 Add/Remove step

Answer 1

Question

Chapter 16.SE, Problem 45MP

Interpretation Introduction

a)

Interpretation:

A structure for methyl orange, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and can attack aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of methyl orange, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Interpretation Introduction

b)

Interpretation:

A structure for allura red, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of allura red, an azo dye, produced when the two reactants shown react and to give the electron pushing mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

A structure for lithol rubine BX, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of lithol rubine BX, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

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This organic molecule is dissolved in an acidic aqueous solution: OH OH A short time later sensitive infrared spectroscopy reveals the presence of a new C = O stretch absorption. That is, there must now be a new molecule present with at least one C = O bond. In the drawing area below, show the detailed mechanism that could convert the molecule above into the new molecule. Videos 849 Explanation Check C Click and drag to start dwing a structure. # 3 MAR 23 Add/Remove step

||| 7:47 ull 57% ← Problem 19 of 48 Submit Curved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the curved arrows to draw the product of this carbocation rearrangement. Include all lone pairs and charges as appropriate. H 1,2-alkyl shift +

Would the following organic synthesis occur in one step? Add any missing products, required catalysts, inorganic reagents, and other important conditions. Please include a detailed explanation and drawings showing how the reaction may occur in one step.

Answer 2

Question

Chapter 16.SE, Problem 45MP

Interpretation Introduction

a)

Interpretation:

A structure for methyl orange, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and can attack aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of methyl orange, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Interpretation Introduction

b)

Interpretation:

A structure for allura red, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of allura red, an azo dye, produced when the two reactants shown react and to give the electron pushing mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

A structure for lithol rubine BX, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of lithol rubine BX, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Expert Solution & Answer

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Answer 3

Question

Chapter 16.SE, Problem 45MP

Interpretation Introduction

a)

Interpretation:

A structure for methyl orange, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and can attack aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of methyl orange, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Interpretation Introduction

b)

Interpretation:

A structure for allura red, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of allura red, an azo dye, produced when the two reactants shown react and to give the electron pushing mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

A structure for lithol rubine BX, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of lithol rubine BX, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Expert Solution & Answer

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Answer 4

Question

Chapter 16.SE, Problem 45MP

Interpretation Introduction

a)

Interpretation:

A structure for methyl orange, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and can attack aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of methyl orange, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Interpretation Introduction

b)

Interpretation:

A structure for allura red, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of allura red, an azo dye, produced when the two reactants shown react and to give the electron pushing mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

A structure for lithol rubine BX, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of lithol rubine BX, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Expert Solution & Answer

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Answer 5

Chapter 16.SE, Problem 45MP

Interpretation Introduction

a)

Interpretation:

A structure for methyl orange, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and can attack aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of methyl orange, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Interpretation Introduction

b)

Interpretation:

A structure for allura red, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of allura red, an azo dye, produced when the two reactants shown react and to give the electron pushing mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

A structure for lithol rubine BX, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of lithol rubine BX, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Answer 6

Chapter 16.SE, Problem 45MP

Interpretation Introduction

a)

Interpretation:

A structure for methyl orange, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and can attack aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of methyl orange, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Answer 7

Chapter 16.SE, Problem 45MP

Interpretation Introduction

a)

Interpretation:

A structure for methyl orange, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and can attack aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of methyl orange, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Answer 8

Interpretation Introduction

b)

Interpretation:

A structure for allura red, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of allura red, an azo dye, produced when the two reactants shown react and to give the electron pushing mechanism for its formation.

Answer 9

Interpretation Introduction

b)

Interpretation:

A structure for allura red, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of allura red, an azo dye, produced when the two reactants shown react and to give the electron pushing mechanism for its formation.

Answer 10

Interpretation Introduction

c)

Interpretation:

A structure for lithol rubine BX, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of lithol rubine BX, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Answer 11

Interpretation Introduction

c)

Interpretation:

A structure for lithol rubine BX, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.

Concept introduction:

The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.

To draw:

The structure of lithol rubine BX, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.

Answer 12

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Answer 23

Ch. 16.1 - Prob. 1P Ch. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SÅª4. deuterium...Ch. 16.3 - Prob. 5P Ch. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P

Solution Summary: The author explains the structure of methyl orange, an azo dye, produced when the two reactants shown react is drawn and the electron pushing mechanism for its formation.

Chapter 16 Solutions