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IBDP Chemistry: Carbonxylic Acid Derivatives - Acid Anhydrides

Acid Anhydrides

· acid anhydrides,chemistry,IB Chemistry,IBDP Chemistry,carbonxylic acid

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

Acid Anhydrides

  • In this chapter of IBDP Chemistry, it formed from the removal of water (H2O) from 2 carboxylic acid molecules
  • To name, remove ‘acid’ from the parent carboxylic acid name and replace with ‘anhydride’ for the (CO)2O bond system
  • e.g. 2 molecules of ethanoic acid --> ethanoic anhydride + water
  • React in a similar way to acyl chlorides with alcohols, phenols, water, ammonia and amines
  • Less reactive than acyl chlorides
  • Useful for some lab preparations where acyl chlorides may be too reactive
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Reactions of Acid Anhydrides with Water

  • Hydrolysis
  • Acid anhydride + water --> 2 carboxylic acids
  • e.g. ethanoic anhydride + water --> 2 ethanoic acid
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Reactions of Acid Anhydrides with Alcohols

  • In this chapter of IBDP Chemistry, Acid anhydride + alcohol --> ester + carboxylic acid
  • e.g. ethanoic anhydride + methanol --> methyl ethanoate + ethanoic acid
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Reactions of Acid Anhydrides with Ammonia

  • Acid anhydride + ammonia --> primary amide + carboxylic acid
  • e.g. ethanoic anhydride + NH3 --> ethanamide + ethanoic acid
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Reactions of Acid Anhydrides with Amines

  • In this chapter of IBDP Chemistry, Acid anhydride + amine --> N-substituted amide + carboxylic acid
  • e.g. ethanoic anhydride + methyl amine --> N-methylethanamide + ethanoic acid

Nucleophilic Addition-Elimination Reactions

Addition: Step 1

  • Lone pair of electrons from the nucleophile is attracted to and donated to the delta positive Carbon atom in the C=O group of the acyl chloride
  • A dative covalent bond is formed between the nucleophile and the carbonyl Carbon atom
  • The pi bond of the C=O group breaks, forming a negatively charged intermediate

Elimination: Step 2

  • A lone pair of electrons on Oxygen reforms the C=O bond, causing a chloride ion to be removed
  • A proton is also then lost to complete the elimination

Nucleophilic Addition-Elimination Mechanism

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  • Add lone pairs
  • Add any charges from electronegativity etc.
  • Curly arrows- show the transfer of electrons
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  • Add lone pairs
  • Add any charges from electronegativity etc.
  • Curly arrows- show the transfer of electrons
  • Acid anhydrides are symmetrical- doesn’t matter which Carbon is used

This is the end of this topic.

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