Question: Predict the products (if any) of the following acid-base reactions.

  1. formic acid + ammonia
  2. terphthalic acid + excess NaOH
  3. p-toluic acid + sodium trifluoroacetate
  4. α-chloropropionic acid + sodium propionate
  5. benzoic acid + potassium phenoxide

Short Answer

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Answer

a.

b.

c.

d.

e.

Step by step solution

01

Acid-base reactions

In an acid-base reaction, conjugate acid-base pairs are formed. Here, the base accepts protons, whereas acid donates protons, and the reaction ends with conjugate acid and conjugate base.

The general reaction is,

Acid+basesalt+water

02

The reaction between formic acid and ammonia

a. In the reaction between formic acid (HCOOH) and ammonia (NH3), formic acid is an acid, ammonia is a base, so ammonia accepts a proton and formic acid denotes a proton. The product formed is,


Reaction between formic acid and ammonia

03

The reaction between terephthalic acid and excess NaOH

b. In the reaction between terephthalic acid and excess NaOH, terephthalic acid is an acid, and NaOH is a base. So, the loss of a proton from two COOH groups from terephthalic acid occurs, and two water molecules are formed. The product of the reaction is,


Reaction between terephthalic acid and excess NaOH

04

The reaction between p-toluic acid and sodium trifluoroacetate

c. No reaction occurs when p-toluic acid (acid) reacts with sodium trifluoroacetate (salt).

Reaction betweenp-toluic acid and sodium trifluoroacetate

05

The reaction between and sodium propionate

d. When (acid) reacts with sodium propionate (salt), donates its one proton to sodium propionate, and sodium propionate accepts one proton and forms propanoic acid. The reaction is shown below,

Reaction betweenα-cloropropinonicacid and sodium propionate

06

The reaction between benzoic acid and potassium phenoxide 

e. When benzoic acid reacts with potassium phenoxide, benzoic acid donates its one proton to potassium phenoxide and forms PhCOO-K+ .Phenoxide accepts one proton and forms phenol. The reaction is as follows,

Reaction between benzoic acid and potassium phenoxide

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Most popular questions from this chapter

The 2000 Nobel Prize in Chemistry was awarded for work on polyacetylenes. Acetylene can be polymerized using a Ziegler-Natta catalyst. The cis or trans stereochemistry of the products can be controlled by careful selection and preparation of the catalyst. The resulting polyacetylene is an electrical semiconductor with a metallic appearance. cis-Polyacetylene has a copper color, and trans-polyacetylene is silver.

(a) Draw the structures of cis- and trans-polyacetylene.

(b) Use your structures to show why these polymers conduct electricity.

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Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.

(a) propiophenone from propionic acid (two ways, using alkylation of the acid and using Friedel-Crafts acylation)

(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acid

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a) methyl salicylate

(b) methyl formate (bp 32°C)

(c) ethyl phenylacetate

Question: What do the following pKa values tell you about the electron-withdrawing abilities of nitro, cyano, chloro, and hydroxy groups?

Use chemical equations to show how the following accidents cause injury to the clothing involved (not to mention the skin under the clothing!)

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