3.3.9.4 Acyl Chlorides

• The general formula of acyl chlorides is RCOCl, where R is an alkyl group.

  True
• The general formula for acyl chlorides is RCOCl.
• Acyl chlorides have the functional group -COCl.
• Acyl chlorides react readily with nucleophiles due to the highly polarized C-Cl bond.

  True
• The byproduct formed when using PCl5 to prepare acyl chlorides is POCl3.
• The byproducts of SOCl2 reaction are gaseous, making purification easier.


  True
• PCl5 directly replaces the hydroxyl group with chlorine in a single-step conversion.


  True
• Match the property with the corresponding compound

  Functional Group of Carboxylic Acid ↔️ -COOH

  Functional Group of Acyl Chloride ↔️ -COCl

  General Formula of Carboxylic Acid ↔️ RCOOH

  General Formula of Acyl Chloride ↔️ RCOCl
• Match the acyl chloride with its parent carboxylic acid

  Ethanoyl chloride ↔️ Ethanoic acid

  Propanoyl chloride ↔️ Propanoic acid
• Using SOCl2 in the preparation of acyl chlorides results in gaseous byproducts, making purification easier.


  True
• Phosphorus pentachloride (PCl5) replaces the hydroxyl group with a chlorine atom, forming an acyl chloride and phosphorus oxychloride
• Why is phosphoric acid (H3PO3) considered a disadvantage of using phosphorus trichloride (PCl3)?

  It must be removed
• What type of bond in acyl chlorides contributes to their high reactivity?

  Polarized C-Cl bond
• Acyl chlorides are derivatives of carboxylic acids where the -OH group is replaced with a -Cl atom.
• Acyl chlorides are highly reactive compared to carboxylic acids.


  True
• Acyl chlorides feature a -COCl functional group attached to an alkyl chain.
• Acyl chlorides typically have low boiling points.
• The reaction of carboxylic acids with SOCl2 produces byproducts SO2 and HCl.
• Acyl chlorides can be synthesized from carboxylic acids using reagents like thionyl chloride, phosphorus trichloride, and phosphorus pentachloride
• One PCl3 molecule can convert three carboxylic acid molecules to acyl chlorides, forming phosphoric acid as a byproduct
• Acyl chlorides are more reactive than carboxylic acids.


  True
• The nomenclature of acyl chlorides replaces the "-ic acid" ending of the parent carboxylic acid with "-oyl chloride
• Acyl chlorides are soluble in organic solvents and react with water.

  True
• The byproducts of acyl chloride reactions include hydrogen chloride (HCl).


  True
• What byproduct is formed when phosphorus trichloride (PCl3) reacts with carboxylic acids?

  Phosphoric acid (H3PO3)
• Steps in the reaction mechanism of thionyl chloride (SOCl2) with a carboxylic acid

  1️⃣ SOCl2 reacts with the hydroxyl group

  2️⃣ An intermediate ester is formed

  3️⃣ The ester breaks down to form acyl chloride, SO2, and HCl
• The reactive nature of acyl chloride synthesis reagents requires careful handling.


  True
• The hydrolysis of acyl chlorides is faster than that of carboxylic acids.


  True
• Acyl chlorides are highly versatile intermediates in organic synthesis due to their reactivity.


  True
• Why do acyl chlorides not require activation for esterification with alcohols?

  They have a polarized C-Cl bond
• Acyl chlorides are used in polymer synthesis to produce polyesters and polyamides
• Acyl chlorides are named by replacing the "-ic acid" ending of the parent carboxylic acid with "-oyl chloride".
• Match the property with the correct compound:

  Functional Group -COOH ↔️ Carboxylic Acid

  Functional Group -COCl ↔️ Acyl Chloride
• Propanoyl chloride has the formula CH3CH2COCl.


  True
• Match the property with the correct compound:

  Boiling Point: Low ↔️ Acyl Chloride

  Boiling Point: High ↔️ Carboxylic Acid
• Steps in the reaction of a carboxylic acid with thionyl chloride (SOCl2):

  1️⃣ SOCl2 reacts with the hydroxyl group to form an intermediate ester.

  2️⃣ The intermediate breaks down to form RCOCl, SO2, and HCl.
• Steps in the reaction mechanism of SOCl2 with carboxylic acids

  1️⃣ SOCl2 reacts with the hydroxyl group to form an intermediate ester

  2️⃣ The intermediate ester breaks down

  3️⃣ Acyl chloride, SO2, and HCl are formed
• Acyl chlorides are derivatives of carboxylic acids in which the -OH group has been replaced by a chlorine atom
• Acyl chlorides have a -COCl functional group directly attached to an alkyl chain.

  True
• Acyl chlorides have a lower boiling point compared to carboxylic acids