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

Q5: Label each chiral carbon in the following molecules as R or S. Make sure the stereocenter to which each of your R/S assignments belong is perfectly clear to the grader. (8pts) R OCH 3 CI H S 2pts for each R/S HO R H !!! I OH CI HN CI R H

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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Q5: Label each chiral carbon in the following molecules as R or S. Make sure the stereocenter to which each of your R/S assignments belong is perfectly clear to the grader. (8pts) R OCH 3 CI H S 2pts for each R/S HO R H !!! I OH CI HN CI R H

Calculate the proton and carbon chemical shifts for this structure

A. B. b. Now consider the two bicyclic molecules A. and B. Note that A. is a dianion and B. is a neutral molecule. One of these molecules is a highly reactive compound first characterized in frozen noble gas matrices, that self-reacts rapidly at temperatures above liquid nitrogen temperature. The other compound was isolated at room temperature in the early 1960s, and is a stable ligand used in organometallic chemistry. Which molecule is the more stable molecule, and why?

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.

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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.

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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