ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT
ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT
6th Edition
ISBN: 9781266060144
Author: SMITH
Publisher: MCG
Question
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Chapter 16, Problem 37P
Interpretation Introduction

(a)

Interpretation: The products formed by the treatment of A and B with reagent Br2,FeBr3 are to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Expert Solution
Check Mark

Answer to Problem 37P

The products formed by the treatment of A and B with reagent Br2,FeBr3 are shown below.

ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT, Chapter 16, Problem 37P , additional homework tip  1

Explanation of Solution

In the given ball and stick model of A and B, black balls represent carbon atoms, white balls represent hydrogen atoms, red balls represent oxygen atoms, blue ball represents nitrogen atom and brown ball represents bromine atom. Therefore, the structure of A and B is,

ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT, Chapter 16, Problem 37P , additional homework tip  2

Figure 1

Reagent Br2,FeBr3 is used for the bromination of aromatic compounds. The OCH(CH3)2 and NHC(O)CH3 groups are electron releasing groups whereas CHO and Br groups are electron withdrawing groups. The electron withdrawing group directs the incoming electrophile to meta position whereas electron releasing group directs incoming electrophile to ortho and para position.

Hence, the products obtained from the treatment of A and B with reagent Br2,FeBr3 are,

ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT, Chapter 16, Problem 37P , additional homework tip  3

Figure 2

Conclusion

The products formed by the treatment of A and B with reagent Br2,FeBr3 are shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The products formed by the treatment of A and B with reagent HNO3,H2SO4 are to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Expert Solution
Check Mark

Answer to Problem 37P

The products formed by the treatment of A and B with reagent HNO3,H2SO4 are shown below.

ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT, Chapter 16, Problem 37P , additional homework tip  4

Explanation of Solution

The structure of A and B is shown in Figure 1.

Reagent HNO3,H2SO4 is used for the nitration of aromatic compounds. The OCH(CH3)2 and NHC(O)CH3 groups are electron releasing groups whereas CHO and Br groups are electron withdrawing groups. The electron withdrawing group directs the incoming electrophile to meta position whereas electron releasing group directs incoming electrophile to ortho and para position.

Hence, the products obtained from the treatment of A and B with reagent HNO3,H2SO4 are,

ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT, Chapter 16, Problem 37P , additional homework tip  5

Figure 3

Conclusion

The products formed by the treatment of A and B with reagent HNO3,H2SO4 are shown in Figure 3.

Interpretation Introduction

(c)

Interpretation: The products formed by the treatment of A and B with reagent CH3CH2COCl,AlCl3 are to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Expert Solution
Check Mark

Answer to Problem 37P

The products formed by the treatment of A and B with reagent CH3CH2COCl,AlCl3 are shown below.

ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT, Chapter 16, Problem 37P , additional homework tip  6

Explanation of Solution

The structure of A and B is shown in Figure 1.

Reagent CH3CH2COCl,AlCl3 is used for the Friedel-Craft acylation of aromatic compounds. The OCH(CH3)2 and NHC(O)CH3 groups are electron releasing groups whereas CHO and Br groups are electron withdrawing groups. The electron withdrawing group directs the incoming electrophile to meta position whereas electron releasing group directs incoming electrophile to ortho and para position.

Hence, the products obtained from the treatment of A and B with reagent CH3CH2COCl,AlCl3 are,

ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT, Chapter 16, Problem 37P , additional homework tip  7

Figure 4

Conclusion

The products formed by the treatment of A and B with reagent CH3CH2COCl,AlCl3 are shown in Figure 4.

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Chapter 16 Solutions

ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT