Acyl chlorides
8 flashcards to master this topic
List three reagents that can be used to convert a carboxylic acid into an acyl chloride.
Phosphorus trichloride (PCl₃) with heat, phosphorus pentachloride (PCl₅), or thionyl chloride (SOCl₂). These reagents replace the -OH group of the carboxylic acid with a chlorine atom.
Write the general equation for the reaction of an acyl chloride with water.
RCOCl + H₂O → RCOOH + HCl. This hydrolysis reaction produces a carboxylic acid and hydrogen chloride gas.
What type of organic compound is produced when an acyl chloride reacts with an alcohol?
An ester is formed. The reaction is: RCOCl + R'OH → RCOOR' + HCl. Hydrogen chloride gas is also produced.
Write the general equation for the reaction of an acyl chloride with ammonia.
RCOCl + 2NH₃ → RCONH₂ + NH₄Cl. An amide is formed, along with ammonium chloride.
Describe the addition-elimination mechanism of acyl chloride reactions.
The nucleophile (
Outline the reaction of acyl chloride with phenol.
RCOCl + C₆H₅OH → RCOOC₆H₅ + HCl. An ester is formed, along with hydrogen chloride gas. Phenol is benzene ring with an -OH group.
Explain why acyl chlorides are more readily hydrolysed than alkyl chlorides or halogenoarenes.
The carbonyl carbon in acyl chlorides is more δ+ due to the electronegativity of both the oxygen and chlorine atoms. This makes it more susceptible to nucleophilic attack by water. Alkyl chlorides and halogenoarenes are less polarised and the C-Cl bond is stronger.
Write the general equation for the reaction of an acyl chloride with a primary amine.
RCOCl + 2R'NH₂ → RCONHR' + R'NH₃Cl. An N-substituted amide is formed, along with the amine salt.
Ready to test yourself?
Practice with MCQ questions to check your understanding of Acyl chlorides.
Take QuizStudy Mode
Rate each card Hard, Okay, or Easy after flipping.