17.2.3 Acyl Chlorides

• What is the functional group in acyl chlorides that makes them more reactive than carboxylic acids?

  Carbonyl bonded to chlorine
• Acyl chlorides are more reactive than carboxylic acids due to the electron-withdrawing nature of chlorine
• Acyl chlorides feature a carbonyl group bonded to a chlorine atom.
• What is the stability of acyl chlorides compared to carboxylic acids?

  Relatively unstable
• The functional group in acyl chlorides is a carbonyl group bonded to a chlorine atom.
• Acyl chlorides have the general formula R-COCl.
• What suffix replaces "-ic acid" in the nomenclature of acyl chlorides?

  -oyl chloride
• In the nomenclature of acyl chlorides, the suffix "-oyl chloride" replaces -ic acid.
• The acyl group CH3CO- is named ethanoyl.
• Which reagent is commonly used to synthesize acyl chlorides from carboxylic acids?

  Thionyl chloride
• Acyl chlorides can be synthesized by reacting a carboxylic acid with thionyl chloride.
• The reaction of ethanoic acid with thionyl chloride produces ethanoyl chloride, sulfur dioxide, and hydrochloric acid.
• Arrange the nucleophiles in order of their reactivity with acyl chlorides:

  1️⃣ Water

  2️⃣ Alcohol

  3️⃣ Ammonia

  4️⃣ Grignard reagent
• What are the products when acyl chlorides react with water?

  Carboxylic acid and HCl
• Acyl chlorides react with ammonia to form amides.
• Ethanoyl chloride reacts with water to form ethanoic acid and hydrochloric acid.