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

A medicinal chemist at Orgalex Labs, a little known division of a big international pharmaceutical firm, has predicted the major product of the following reacti an early step in the synthesis of Compound R40 (rumored to be a cure for rhinitis, spontaneous combustion, and bad luck): or=0x0 HBr OH As Vice-President of Research, it's your job to decide whether the chemist has made a reasonable prediction. • If your answer is yes, these could be the major products of the reaction, draw the complete mechanism for the reaction below. • If your answer is no, check the box under the drawing area. Ö U OH Br H-Br Add/Remove step Click and drag to start drawing a structure.

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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A medicinal chemist at Orgalex Labs, a little known division of a big international pharmaceutical firm, has predicted the major product of the following reacti an early step in the synthesis of Compound R40 (rumored to be a cure for rhinitis, spontaneous combustion, and bad luck): or=0x0 HBr OH As Vice-President of Research, it's your job to decide whether the chemist has made a reasonable prediction. • If your answer is yes, these could be the major products of the reaction, draw the complete mechanism for the reaction below. • If your answer is no, check the box under the drawing area. Ö U OH Br H-Br Add/Remove step Click and drag to start drawing a structure.

Briefly describe the role of this molecule as it relates to bees. Propose Two reasonable syntheses of this molecule from benzene. there are multiple syntheses possible (the first proposed synthesis required twelve steps) HO. OH

Diazomethane, CH2N2, is used in the organic chemistry laboratory despite its danger because it produces very high yields and is selective for reaction with carboxylic acids. Write the products of the following reactions.

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.

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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