Chapter 22, Problem 22.14P

Interpretation Introduction

(a)

Interpretation: The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{H}}_{\text{2}}\text{O}$ are to be drawn.

Concept introduction: Anhydrides involve two carbonyl groups. The nucleophilic substitution reaction of anhydride involves the attack of nucleophilic at one carbonyl group, which causes the second carbonyl group to be the part of leaving group.

Answer to Problem 22.14P

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{H}}_{\text{2}}\text{O}$ are,

Explanation of Solution

The given treatment involves reaction of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{H}}_{\text{2}}\text{O}$.

Anhydrides involve two carbonyl groups. The nucleophilic substitution reaction of anhydride involves the attack of nucleophilic at one carbonyl group, which causes the second carbonyl group to be the part of leaving group.

Anhydrides yield two equivalents of carboxylic acids, when they are treated with ${\text{H}}_{\text{2}}\text{O}$.

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{H}}_{\text{2}}\text{O}$ are drawn below.

Figure 1

Conclusion

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{H}}_{\text{2}}\text{O}$ are drawn in Figure 1.

Interpretation Introduction

(b)

Interpretation: The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{CH}}_{\text{3}}\text{OH}$ are to be drawn.

Concept introduction: Anhydrides involve two carbonyl groups. The nucleophilic substitution reaction of anhydride involves the attack of nucleophilic at one carbonyl group, which causes the second carbonyl group to be the part of leaving group.

Answer to Problem 22.14P

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{CH}}_{\text{3}}\text{OH}$ are,

Explanation of Solution

The given treatment involves reaction of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{CH}}_{\text{3}}\text{OH}$.

Anhydrides involve two carbonyl groups. The nucleophilic substitution reaction of anhydride involves the attack of nucleophilic at one carbonyl group, which causes the second carbonyl group to be the part of leaving group.

Anhydrides yield esters, and carboxylic acids, when they are treated with ${\text{CH}}_{\text{3}}\text{OH}$ (an alcohol).

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{CH}}_{\text{3}}\text{OH}$ are drawn below.

Figure 2

Conclusion

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{CH}}_{\text{3}}\text{OH}$ are drawn in Figure 2.

Interpretation Introduction

(c)

Interpretation: The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{NH}}_{\text{3}}$ (excess) are to be drawn.

Concept introduction: Anhydrides involve two carbonyl groups. The nucleophilic substitution reaction of anhydride involves the attack of nucleophilic at one carbonyl group, which causes the second carbonyl group to be the part of leaving group.

Answer to Problem 22.14P

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{NH}}_{\text{3}}$ (excess) are,

Explanation of Solution

The given treatment involves reaction of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{NH}}_{\text{3}}$ (excess).

Anhydrides involve two carbonyl groups. The nucleophilic substitution reaction of anhydride involves the attack of nucleophilic at one carbonyl group, which causes the second carbonyl group to be the part of leaving group.

Anhydrides yield amide and an ammonium salt of carboxylic acid, when they are treated with ${\text{NH}}_{\text{3}}$ (excess).

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{NH}}_{\text{3}}$ (excess) are drawn below.

Figure 3

Conclusion

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\text{NH}}_{\text{3}}$ (excess) are drawn in Figure 3.

Interpretation Introduction

(d)

Interpretation: The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{NH}$ (excess) are to be drawn.

Concept introduction: Anhydrides involve two carbonyl groups. The nucleophilic substitution reaction of anhydride involves the attack of nucleophilic at one carbonyl group, which causes the second carbonyl group to be the part of leaving group.

Answer to Problem 22.14P

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{NH}$ (excess) are,

Explanation of Solution

The given treatment involves reaction of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{NH}$ (excess).

Anhydrides involve two carbonyl groups. The nucleophilic substitution reaction of anhydride involves the attack of nucleophilic at one carbonyl group, which causes the second carbonyl group to be the part of leaving group.

Anhydrides yield amide and an ammonium salt of carboxylic acid, when they are treated with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{NH}$ (excess).

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{NH}$ (excess) are drawn below.

Figure 4

Conclusion

The products formed by the treatment of benzoic anhydride $\left[{\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ with ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{NH}$ (excess) are drawn in Figure 4.