Chapter 17: Problem 106

Show how a carboxylic acid, \(\mathrm{R}-\mathrm{COOH}\), reacts with a tertiary amine, \(\mathrm{NR}_{3}\).

Short Answer

Expert verified

A carboxylic acid (R-COOH) reacts with a tertiary amine (NR3) in a Brønsted-Lowry acid-base reaction. The carboxylic acid donates a proton (H+) to the tertiary amine, forming a carboxylate anion (R-COO⁻) and an ammonium cation (NR4⁺). The balanced reaction equation is: \[ R-COOH+\mathrm{NR}_3 \rightarrow R-COO^-+\mathrm{NR}_4^+ \] Thus, a carboxylate salt is formed as the product.

Step by step solution

Identify the acidic and basic components

In this reaction, the carboxylic acid (R-COOH) acts as the acidic component in the reaction because it donates a proton (H+). The tertiary amine (NR3) acts as the basic component as it accepts the proton.

Draw the Lewis structures of the reactants

To better understand the reaction, it's helpful to draw the Lewis structures of carboxylic acid (R-COOH) and tertiary Amine (NR3). Carboxylic acid (R-COOH): ``` O || R--C--O--H ``` Tertiary amine (NR3): ``` R1 | R2--N--R3 ```

Reaction between the reactants

The nitrogen in the tertiary amine (NR3) has a lone pair of electrons that can act as a nucleophile. The proton in the carboxylic acid (R-COOH) can form a bond with the nucleophile. This results in the transfer of a proton from the carboxylic acid to the tertiary amine.

Form the products

After the proton transfer, the R-COOH molecule becomes R-COO⁻ and the NR3 molecule becomes NR4⁺. The charge on both the carboxylate anion and the ammonium cation is now balanced. Carboxylate anion (R-COO⁻): ``` O || R--C--O⁻ ``` Ammonium cation (NR4⁺): ``` R1 | R2--N--R3 | H ```

Final reaction equation

Combining all the steps above, we can now write the full balanced reaction equation between a carboxylic acid (R-COOH) and a tertiary amine (NR3): \[ R-COOH+\mathrm{NR}_3 \rightarrow R-COO^-+\mathrm{NR}_4^+ \] In conclusion, a carboxylic acid reacts with a tertiary amine to form a carboxylate anion and an ammonium cation, which together form a carboxylate salt.

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Show how a carboxylic acid, \(\mathrm{R}-\mathrm{COOH}\), reacts with a tertiary amine, \(\mathrm{NR}_{3}\).

Short Answer

Step by step solution

Identify the acidic and basic components

Draw the Lewis structures of the reactants

Reaction between the reactants

Form the products

Final reaction equation

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