a) Interpretation: The flaw in the synthesis given is to be stated. Concept introduction: In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO 4 the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected. To state: The flaw in the synthesis given.

Question

Please draw the structure in the box that is consistent with all the spectral data and alphabetically label all of the equivalent protons in the structure (Ha, Hb, Hc....) in order to assign all the proton NMR peaks. The integrations are computer generated and approximate the number of equivalent protons. Molecular formula: C13H1802 14 13 12 11 10 11 (ppm) Structure with assigned H peaks 2.08 3.13

Answer 1

Question

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

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Please draw the structure in the box that is consistent with all the spectral data and alphabetically label all of the equivalent protons in the structure (Ha, Hb, Hc....) in order to assign all the proton NMR peaks. The integrations are computer generated and approximate the number of equivalent protons. Molecular formula: C13H1802 14 13 12 11 10 11 (ppm) Structure with assigned H peaks 2.08 3.13

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Firefly luciferin exhibits three rings. Identify which of the rings are aromatic. Identify which lone pairs are involved in establishing aromaticity. The lone pairs are labeled A-D below.

Answer 2

Question

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

Expert Solution & Answer

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Answer 3

Question

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

Expert Solution & Answer

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Answer 4

Question

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

Expert Solution & Answer

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Answer 5

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

Answer 6

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Answer 7

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Answer 8

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Answer 9

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Answer 10

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

Answer 11

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

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 that in aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups.

Chapter 16 Solutions