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What compounds are formed from the reaction of benzoyl chloride with the following reagents?
e. aqueous NaOH
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Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblema 50g,h
Bruice 8th EditionCh. 15 - Reactions of Carboxylic Acids and Carboxylic Acid DerivativesProblema 50g,hCapitolo 15, Problema 50g,h
What compounds are formed from the reaction of benzoyl chloride with the following reagents?
g. excess benzylamine
h. 4-chlorophenol
Guida verificata passo dopo passo1
Identify the functional group in benzoyl chloride. Benzoyl chloride contains an acyl chloride group (-COCl), which is highly reactive and undergoes nucleophilic acyl substitution reactions.
Understand the reaction mechanism with benzylamine (excess). Benzylamine (C6H5CH2NH2) is a nucleophile that will attack the carbonyl carbon of benzoyl chloride. The reaction proceeds via a nucleophilic acyl substitution mechanism, where the amine replaces the chloride ion (Cl⁻) to form a benzamide derivative.
Write the general reaction for part (g): \( \text{C6H5COCl} + \text{C6H5CH2NH2} \rightarrow \text{C6H5CONHCH2C6H5} + \text{HCl} \). Since benzylamine is in excess, it can also neutralize the HCl formed during the reaction, preventing side reactions.
Understand the reaction mechanism with 4-chlorophenol. 4-Chlorophenol (C6H4ClOH) is a phenol derivative, and the hydroxyl group (-OH) acts as a nucleophile. It will attack the carbonyl carbon of benzoyl chloride, replacing the chloride ion (Cl⁻) to form an ester.
Write the general reaction for part (h): \( \text{C6H5COCl} + \text{C6H4ClOH} \rightarrow \text{C6H5COOC6H4Cl} + \text{HCl} \). The product is an ester (benzoyl-4-chlorophenyl ester), and HCl is released as a byproduct.
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Acyl Chlorides
Acyl chlorides, such as benzoyl chloride, are reactive compounds containing a carbonyl group (C=O) bonded to a chlorine atom. They are known for their ability to undergo nucleophilic acyl substitution reactions, where the chlorine atom is replaced by a nucleophile. Understanding the reactivity of acyl chlorides is crucial for predicting the products formed when they react with various nucleophiles.
Video consigliato:
01:57
Recognizing acyl chlorides and anhydrides.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, leading to the replacement of a leaving group. In the case of benzoyl chloride, nucleophiles like benzylamine and 4-chlorophenol can attack the carbonyl carbon, resulting in the formation of amides or esters, respectively. This concept is essential for understanding how different reagents interact with acyl chlorides.
Video consigliato:
01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Amide Formation
Amide formation occurs when an acyl chloride reacts with an amine, resulting in the creation of an amide bond (C=O-N). In the reaction with excess benzylamine, benzoyl chloride will yield N-benzoylbenzylamine, showcasing the transformation of the acyl chloride into a more stable amide. This process is significant in organic synthesis, as amides are important functional groups in various chemical compounds.
Video consigliato:
01:33Amide Nomenclature
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