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IBDP Chemistry: Carbonxylic Acid Derivatives - Acyl Chlorides

Acyl Chlorides

· chemistry,IB Chemistry,IBDP Chemistry,carbonxylic acid,Acyl Chlorides

In this chapter of IBDP Chemistry, we will learn about carbonxylic acid derivatives - Acyl Chlorides.

Acyl Chlorides

  • In this chapter of IBDP Chemistry, it named after the parent carboxylic acid from which it is derived
  • Remove the ‘-oic acid’ suffix and replace with ‘-oyl chloride’ for the COCl bond system
  • e.g. propanoic acid to propanoyl chloride
  • Very reactive and so very useful in organic synthesis
  • They are easily converted into carboxylic acid derivatives e.g. esters and amides with good yields
  • React with nucleophiles by losing the chloride ion whilst retaining the C=O double bond

Preparation of Acyl Chloride

  • In this chapter of IBDP Chemistry, it must be prepared in a fume cupboard as the products are harmful- produce SO2 and HCl as gases
  • Prepared from their parent carboxylic acid + thionyl chloride (SOCl2)
  • e.g. propanoic acid(aq) + thionyl chloride(aq)  --> propanoyl chloride(aq) + SO2(g) + HCl(g)
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Reactions of Acyl Chlorides with Alcohols

Acyl chloride + alcohol --> ester + HCl (hydrogen chloride gas)

  • In this chapter of IBDP Chemistry, it is esterification reaction
  • Alcoholic conditions
  • e.g. ethanoyl chloride + propan-1-ol --> propyl ethanoate + HCl
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Acyl chloride + phenol --> phenyl ester + HCl

  • Carboxylic acids are not reactive enough to form esters with phenols
  • Acyl chlorides and acid anhydrides are both much more reactive than carboxylic acids

e.g. ethanoyl chloride + phenol --> phenylethanoate + HCl

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Reactions of Acyl Chlorides with Water

  • Hydrolysis
  • React instantly in cold water
  • Violent reaction takes place- evolution of dense, steamy hydrogen chloride fumes (white)
  • Very exothermic

Acyl chloride + water --> carboxylic acid + hydrogen chloride

  • e.g. ethanoyl chloride + water --> ethanoic acid + HCl
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Reactions of Acyl Chlorides with Ammonia

  • In this chapter of IBDP Chemistry, ammonia can act as a nucleophile by donating the lone pair of electrons on the Nitrogen atom to an electron deficient species to form primary amides

Acyl chloride + ammonia --> primary amide + ammonium chloride

  • A primary amide is when the Nitrogen atom is attached to one Carbon only and 2 Hydrogen atoms
  • e.g. ethanoyl chloride + ammonia --> ethanamide + ammonium chloride
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This is the end of this topic.

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