Chapter 29, Problem 29.60P

Draw the organic products formed in each reaction.

a. d.

b. e.

c. f.

Interpretation Introduction

(a)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: An ester is formed by the reaction of carboxylic with alcohol in the presence of an acid catalyst. This reaction is known as Fischer Esterification.

Answer to Problem 29.60P

The organic product formed in given reaction is,

Explanation of Solution

In the given reaction, the oxygen of carboxyl group takes a proton from an acid. The carbon of carbonyl carbon acts as an electrophile where the attacking of oxygen of alcohol takes place and gives 1, 2-addition. The transfer of proton takes place leads to the elimination of water molecule. In the final step, deprotonation takes place. The corresponding reaction is shown below.

Figure 1

Conclusion

The organic product formed in given reaction is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: Treatment of amine with t-butoxypyrocarbonate in the presence of triethyl amine yields t-butoxy carbonyl group. ${\left(\text{Boc}\right)}_{\text{2}}\text{O}$ is used to protect the amines in the presence of ${\text{Et}}_{\text{3}}\text{N}$.

Answer to Problem 29.60P

The organic product formed in given reaction is,

Explanation of Solution

The full form of ${\left(\text{Boc}\right)}_{\text{2}}\text{O}$ is t-butoxypyrocarbonate. It protects the amines towards the action of ${\text{Et}}_{\text{3}}\text{N}$. The reaction of given compound with ${\left(\text{Boc}\right)}_{\text{2}}\text{O}$ in the presence of ${\text{Et}}_{\text{3}}\text{N}$ introduces t-butoxy carbonyl group in a product. The reaction is shown below.

Figure 2

Conclusion

The organic product formed in given reaction is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: The full form of DCC is dicyclohexylcarbodiimide. It is a dehydrating agent which is used to synthesized amides, nitriles and ketones.

Answer to Problem 29.60P

The organic product formed in given reaction is,

Explanation of Solution

As amine are basic in nature and they have tendency to convert carboxylic acid to carboxylate. In the given reaction, carboxylic acid adds to the DCC and forms a good leaving group which displaces by amine in nucleophilic substitution reaction. DCC forms an amide linkage. The corresponding reaction is shown below.

Figure 3

Conclusion

The organic product formed in given reaction is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: $\text{Pd}-\text{C}$ is reagent which is used in hydrogenation reaction. In the presence of hydrogen gas it reduces alkene to alkane.

Answer to Problem 29.60P

The organic product formed in given reaction is,

Explanation of Solution

In the given reaction, the reactant undergoes catalytic reduction in the presence of $\text{Pd}-\text{C}$ reagent. It reduces ester into alcohol. The corresponding reaction is shown below.

Figure 4

Conclusion

The organic product formed in given reaction is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: The halogenated derivative of acetic acid is TFA. The full form of TFA is trifluoroacetic acid. It is used to break the ester bond in peptide synthesis.

Answer to Problem 29.60P

The organic products formed in given reaction are,

Explanation of Solution

Treatment of given compound with trifluoroacetic acid cleaves the bond $\text{I}$ (mark in red color) to form a product. The corresponding reaction is shown below.

Figure 5

Conclusion

The organic product formed in given reaction is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: The organic products formed in given reaction are to be drawn.

Concept introduction: The full form of Fmoc-Cl is fluorenylmethyloxycarbonyl chloride. The molecular formula of Fmoc-Cl is ${\text{C}}_{\text{15}}{\text{H}}_{\text{11}}{\text{ClO}}_{\text{2}}$. It introduces a group which protects the amine group in organic synthesis.

Answer to Problem 29.60P

The organic product formed in given reaction is,

Explanation of Solution

The Fmoc-Cl introduces a group i.e. comF which protects the amine group towards action of sodium carbonate. In the given reaction, treatment of given compound with sodium carbonate in the presence of Fmoc-Cl forms a product with comF group as shown below.

Figure 6

Conclusion

The organic product formed in given reaction is shown in Figure 6.