Chapter 18, Problem 18.36P

Draw the products formed when phenol $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{OH}\right)$ is treated with each set of reagents.

a. ${\text{HNO}}_{\text{3}}\text{,}{\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ e. ${\text{Br}}_{\text{2}},{\text{FeBr}}_{\text{3}}$ i. product in (d), then $\text{Zn}\left(\text{Hg}\right)\text{,}\text{HCl}$

b. ${\text{SO}}_3\text{,}{\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ f. ${\text{Br}}_{\text{2}}$ j. product in (d), then ${\text{NH}}_2{\text{NH}}_2\text{,}{\text{OH}}^{-}$

c. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{Cl,}{\text{AlCl}}_3$ g. ${\text{Cl}}_{\text{2}},{\text{FeCl}}_{\text{3}}$ k. product in (c), then ${\text{Br}}_{\text{2}},hv$

d. ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{CHCOCl,}{\text{AlCl}}_3$ h. product in (a), then $\text{Sn,}\text{HCl}$ l. product in (c), then ${\text{KMnO}}_{\text{4}}$

Interpretation Introduction

(a)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

Phenol undergoes nitration reaction on treatment with ${\text{HNO}}_{\text{3}}\text{,}{\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$. The $\text{OH}$ group is an electron releasing group and it directs an incoming electrophile to ortho and para position. Therefore, nitration takes place at ortho and para position as shown in Figure 1

Figure 1

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

An aromatic compound undergoes sulphonation on reaction with ${\text{SO}}_3$ in the presence of ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$. This reagent generates sulphonium ion ${}^{+}{\text{SO}}_{\text{3}}\text{H}$ which acts as electrophile and give reaction on ortho and para position. Hence, the reaction of phenol with given reagents is,

Figure 2

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

An aromatic compound undergoes Friedel-Craft alkylation on reaction with $\text{RCl}$ in the presence of ${\text{AlCl}}_{\text{3}}$. Hence, the reaction of phenol with given reagents is,

Figure 3

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

An aromatic compound undergoes Friedel-Craft acylation on reaction with $\text{ROCl}$ in the presence of ${\text{AlCl}}_{\text{3}}$. Hence, the reaction of phenol with given reagents is,

Figure 4

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

The benzene ring is activated in phenol due to the presence of strong electron donating group. In bromination, bromonium acts as electrophile and produces $\text{2, 4, 6}$-tribromophenol. The corresponding chemical reaction is shown below.

Figure 5

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

Phenol undergoes mono bromination with bromine without catalyst. The corresponding chemical reaction is shown below.

Figure 6

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 6.

Interpretation Introduction

(g)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

The benzene ring is activated in phenol due to the presence of strong electron donating group. In chlorination, chloronium acts as electrophile and produces $\text{2, 4, 6}$-trichlorophenol. The corresponding chemical reaction is shown below.

Figure 7

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 7.

Interpretation Introduction

(h)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

The ${\text{NO}}_{\text{2}}$ group of nitrophenolreduces to ${\text{NH}}_{\text{2}}$ on reaction with $\text{Sn,}\text{HCl}$. Hence, the product obtained by the reaction of $2$-nitrophenol and $4$-nitrophenol is $2$-aminophenol and $4$-aminophenol, respectivelyas shown in Figure 8.

Figure 8

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 8.

Interpretation Introduction

(i)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

The carbonyl group $-\text{CO}-$ of acyl group reduced to $-{\text{CH}}_{\text{2}}-$ on reaction with $\text{Zn}\left(\text{Hg}\right)\text{,}\text{HCl}$. The corresponding chemical reaction is shown below.

Figure 9

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 9.

Interpretation Introduction

(j)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

The carbonyl group $-\text{CO}-$ of acyl group reduced to $-{\text{CH}}_{\text{2}}-$ on reaction with ${\text{NH}}_2{\text{NH}}_2\text{,}{\text{OH}}^{-}$. The corresponding chemical reaction is shown below.

Figure 10

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 10.

Interpretation Introduction

(k)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

The bromine group attaches to the side chain of the aromatic compound on reaction with ${\text{Br}}_{\text{2}}$ in the presence of light. The corresponding chemical reaction is shown below.

Figure 11

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 11.

Interpretation Introduction

(l)

Interpretation: The products formed by the treatment of phenol with given reagents 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.

Answer to Problem 18.36P

The products formed by the treatment of phenol with given reagents are shown below:

Explanation of Solution

The alkyl group oxidizes to $\text{COOH}$ on reaction with oxidizing agent ${\text{KMnO}}_{\text{4}}$. The corresponding chemical reaction is shown below.

Figure 12

Conclusion

The products formed by the treatment of phenol with given reagents are shown in Figure 12.