Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Problem 50k

Chapter 16, Problem 50k

What compounds are formed from the reaction of benzoyl chloride with the following reagents?
k. potassium formate

Verified step by step guidance

Step 1: Recognize the functional group in benzoyl chloride. Benzoyl chloride contains an acyl chloride functional group (-COCl) attached to a benzene ring. Acyl chlorides are highly reactive and can undergo nucleophilic acyl substitution reactions.

Step 2: Identify the reagent, potassium formate (HCOOK). Potassium formate is the potassium salt of formic acid (HCOOH) and acts as a nucleophile due to the presence of the formate ion (HCOO⁻).

Step 3: Understand the reaction mechanism. In the presence of potassium formate, the nucleophilic formate ion (HCOO⁻) attacks the carbonyl carbon of the benzoyl chloride. This is a nucleophilic acyl substitution reaction, where the chloride ion (Cl⁻) is displaced as the leaving group.

Step 4: Predict the product. The substitution of the chloride ion by the formate ion results in the formation of benzoyl formate (C₆H₅COOCHO), which is an ester. The byproduct of the reaction is potassium chloride (KCl).

Step 5: Summarize the reaction. The overall reaction can be written as: C₆H₅COCl + HCOOK → C₆H₅COOCHO + KCl. This shows the formation of benzoyl formate and potassium chloride as the products.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.

Video duration:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Benzoyl Chloride

Benzoyl chloride is an acyl chloride derived from benzoic acid. It is a reactive compound that can undergo nucleophilic acyl substitution reactions. In these reactions, the chlorine atom is replaced by a nucleophile, leading to the formation of various products depending on the nucleophile used.

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the replacement of a leaving group (like chloride) with the nucleophile. This reaction is crucial for understanding how different reagents interact with acyl chlorides, resulting in diverse organic compounds.

Potassium Formate

Potassium formate is the potassium salt of formic acid and acts as a nucleophile in organic reactions. When it reacts with benzoyl chloride, the formate ion can attack the carbonyl carbon, leading to the formation of benzoyl formate. This reaction exemplifies how carboxylate ions can participate in nucleophilic acyl substitution.

Recommended video:

Guided course

02:26

Formation of Enolates

Related Practice

Textbook Question

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

g. excess benzylamine

h. 4-chlorophenol

1090

views

Textbook Question

Because bromocyclohexane is a secondary alkyl halide, both cyclohexanol and cyclohexene are formed when the alkyl halide reacts with hydroxide ion. Suggest a method to synthesize cyclohexanol from bromocyclohexane that forms little or no cyclohexene.

1404

views

Textbook Question

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

i. isopropyl alcohol

1522

views

Textbook Question

What compounds are obtained from the following hydrolysis reactions?

1229

views

Textbook Question