Chapter 18, Problem 42P

Draw the structure for each of the following:

a. phenol

b. benzyl phenyl ether

c. benzonitrile

d. benzaldehyde

e. anisole

f. styrene

g. toluene

h. tert-buty lbenzene

i. benzyl chloride

Interpretation Introduction

Interpretation:

The structure of phenol is to be drawn.

Concept introduction:

Phenols are defined as those compounds in which hydroxy group is attached directly to the benzene ring. Phenols and alcohols have so many similar properties.

The reactivity of benzene ring towards electrophilic aromatic substitution reactions is enhanced by the activating substituents. The deactivating substituents make the benzene ring less reactive. Some of the activating substituents are $-{\text{NH}}_{\text{2}},-\text{OH},-\text{R},-\text{OR}$. Some of the deactivating substituents are $-\text{CHO},-\text{COOR},-\text{X},-\text{COCl}$. Activating substituents are ortho-para director while deactivating substituents are meta director.

Answer to Problem 42P

The structure of phenol is shown below.

Figure 1

Explanation of Solution

The structure of phenol is drawn as follows.

The first step is to draw the structure of benzene ring. Then $\text{OH}$ group is placed at any carbon atom in the benzene ring.

Thus, the structure of phenol is shown below.

Figure 1

Interpretation Introduction

Interpretation:

The structure of benzyl phenyl ether is to be drawn.

Concept introduction:

The reactivity of benzene ring towards electrophilic aromatic substitution reactions is enhanced by the activating substituents. The deactivating substituents make the benzene ring less reactive. Some of the activating substituents are $-{\text{NH}}_{\text{2}},-\text{OH},-\text{R},-\text{OR}$. Some of the deactivating substituents are $-\text{CHO},-\text{COOR},-\text{X},-\text{COCl}$. Activating substituents are ortho-para director while deactivating substituents are meta director.

Answer to Problem 42P

The structure of benzyl phenyl ether is shown below.

Figure 2

Explanation of Solution

The structure of benzyl phenyl ether is drawn as follows.

The first step is to draw the structure of benzene ring. Then ${\text{CH}}_{\text{2}}$ group is placed at first carbon atom in the benzene ring. Then in the next benzene ring, an oxygen atom is placed at the first carbon atom in the second benzene ring. Then benzene ring with ${\text{CH}}_{\text{2}}$ group is attached to the oxygen atom that is attached to second benzene ring.

Thus, the structure of benzyl phenyl ether is shown below.

Figure 2

Interpretation Introduction

Interpretation:

The structure of benzonitrile is to be drawn.

Concept introduction:

The reactivity of benzene ring towards electrophilic aromatic substitution reactions is enhanced by the activating substituents. The deactivating substituents make the benzene ring less reactive. Some of the activating substituents are $-{\text{NH}}_{\text{2}},-\text{OH},-\text{R},-\text{OR}$. Some of the deactivating substituents are $-\text{CHO},-\text{COOR},-\text{X},-\text{COCl}$. Activating substituents are ortho-para director while deactivating substituents are meta director.

Answer to Problem 42P

The structure of benzonitrile is shown below.

Figure 3

Explanation of Solution

The structure of benzonitrile is drawn as follows.

The first step is to draw the structure of benzene ring. Then $\text{C}\equiv \text{N}$ group is placed at any carbon atom in the benzene ring.

Thus, the structure of benzonitrile is shown below.

Figure 3

Interpretation Introduction

Interpretation:

The structure of benzaldehyde is to be drawn.

Concept introduction:

The reactivity of benzene ring towards electrophilic aromatic substitution reactions is enhanced by the activating substituents. The deactivating substituents make the benzene ring less reactive. Some of the activating substituents are $-{\text{NH}}_{\text{2}},-\text{OH},-\text{R},-\text{OR}$. Some of the deactivating substituents are $-\text{CHO},-\text{COOR},-\text{X},-\text{COCl}$. Activating substituents are ortho-para director while deactivating substituents are meta director.

Answer to Problem 42P

The structure of benzaldehyde is shown below.

Figure 4

Explanation of Solution

The structure of benzaldehyde is drawn as follows.

The first step is to draw the structure of benzene ring. Then $\text{CHO}$ group is placed at any carbon atom in the benzene ring.

Thus, the structure of benzaldehyde is shown below.

Figure 4

Interpretation Introduction

Interpretation:

The structure of anisole is to be drawn.

Concept introduction:

The reactivity of benzene ring towards electrophilic aromatic substitution reactions is enhanced by the activating substituents. The deactivating substituents make the benzene ring less reactive. Some of the activating substituents are $-{\text{NH}}_{\text{2}},-\text{OH},-\text{R},-\text{OR}$. Some of the deactivating substituents are $-\text{CHO},-\text{COOR},-\text{X},-\text{COCl}$. Activating substituents are ortho-para director while deactivating substituents are meta director.

Answer to Problem 42P

The structure of anisole is shown below.

Figure 5

Explanation of Solution

The structure of anisole is drawn as follows.

The first step is to draw the structure of benzene ring. Then ${\text{OCH}}_{\text{3}}$ group is placed at any carbon atom in the benzene ring.

Thus, the structure of anisole is shown below.

Figure 5

Interpretation Introduction

Interpretation:

The structure of styrene is to be drawn.

Concept introduction:

The reactivity of benzene ring towards electrophilic aromatic substitution reactions is enhanced by the activating substituents. The deactivating substituents make the benzene ring less reactive. Some of the activating substituents are $-{\text{NH}}_{\text{2}},-\text{OH},-\text{R},-\text{OR}$. Some of the deactivating substituents are $-\text{CHO},-\text{COOR},-\text{X},-\text{COCl}$. Activating substituents are ortho-para director while deactivating substituents are meta director.

Answer to Problem 42P

The structure of styrene is shown below.

Figure 6

Explanation of Solution

The structure of styrene is drawn as follows.

The first step is to draw the structure of benzene ring. Then $\text{CH}={\text{CH}}_{\text{2}}$ ethylene is placed at any carbon atom in the benzene ring.

Thus, the structure of styrene is shown below.

Figure 6

Interpretation Introduction

Interpretation: The structure of toluene is to be drawn.

Concept introduction:

The reactivity of benzene ring towards electrophilic aromatic substitution reactions is enhanced by the activating substituents. The deactivating substituents make the benzene ring less reactive. Some of the activating substituents are $-{\text{NH}}_{\text{2}},-\text{OH},-\text{R},-\text{OR}$. Some of the deactivating substituents are $-\text{CHO},-\text{COOR},-\text{X},-\text{COCl}$. Activating substituents are ortho-para director while deactivating substituents are meta director.

Answer to Problem 42P

The structure of toluene is shown below.

Figure 7

Explanation of Solution

The structure of toluene is drawn as follows.

The first step is to draw the structure of benzene ring. Then ${\text{CH}}_{\text{3}}$ group is placed at any carbon atom in the benzene ring.

Thus, the structure of toluene is shown below.

Figure 7

Interpretation Introduction

Interpretation: The structure of tert-butyl benzene is to be drawn.

Concept introduction:

The reactivity of benzene ring towards electrophilic aromatic substitution reactions is enhanced by the activating substituents. The deactivating substituents make the benzene ring less reactive. Some of the activating substituents are $-{\text{NH}}_{\text{2}},-\text{OH},-\text{R},-\text{OR}$. Some of the deactivating substituents are $-\text{CHO},-\text{COOR},-\text{X},-\text{COCl}$. Activating substituents are ortho-para director while deactivating substituents are meta director.

Answer to Problem 42P

The structure of tert-butyl benzene is shown below.

Figure 8

Explanation of Solution

The structure of tert-butyl benzene is drawn as follows.

The first step is to draw the structure of benzene ring. Then ${\text{CH}}_3-\text{CH}\left({\text{CH}}_{\text{3}}\right)-{\text{CH}}_{\text{3}}$ tert-butyl group is placed at any carbon atom in the benzene ring.

Thus, the structure of tert-butyl benzene is shown below.

Figure 8

Interpretation Introduction

Interpretation:

The structure of benzyl chloride is to be drawn.

Concept introduction:

The reactivity of benzene ring towards electrophilic aromatic substitution reactions is enhanced by the activating substituents. The deactivating substituents make the benzene ring less reactive. Some of the activating substituents are $-{\text{NH}}_{\text{2}},-\text{OH},-\text{R},-\text{OR}$. Some of the deactivating substituents are $-\text{CHO},-\text{COOR},-\text{X},-\text{COCl}$. Activating substituents are ortho-para director while deactivating substituents are meta director.

Answer to Problem 42P

The structure of benzyl chloride is shown below.

Figure 9

Explanation of Solution

The structure of benzyl chloride is drawn as follows.

The first step is to draw the structure of benzene ring. Then ${\text{CH}}_2\text{Cl}$ group is placed at any carbon atom in the benzene ring.

Thus, the structure of benzyl chloride is shown below.

Figure 9