Topic 17 - Acyl chlorides:

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8 Terms

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Acyl chlorides - naming:

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2
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Explain why acyl chlorides are so reactive:

  • 2 polar bonds (C=O and C-Cl)

  • C-Cl bond is quite weak as it is a large atom so a longer bond

  • Therefore extremely reactive compound

<ul><li><p>2 polar bonds (C=O and C-Cl)</p></li><li><p>C-Cl bond is quite weak as it is a large atom so a longer bond</p></li><li><p>Therefore extremely reactive compound </p></li></ul>
3
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Formation of acyl chlorides:

  • add PCl5 to carboxylic acids

  • As PCl5 is added - steamy fumes of HCl is produced (which turn damp blue litmus paper red)

  • HCl is a toxic gas therefore reaction should be carried out in a fume cupboard

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Reaction of acyl chlorides with water:

  • makes a carboxylic acid (and HCl)

  • Steamy fumes which turn damp blue litmus paper red

<ul><li><p>makes a carboxylic acid (and HCl)</p></li><li><p>Steamy fumes which turn damp blue litmus paper red</p></li></ul>
5
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Reaction of acyl chlorides with alcohols:

  • forms an ester (and HCl)

  • Same reaction as with a carboxylic acid (acyl chloride used in place of acid)

  • However - acyl chlorides are more reactive than carboxylic acids, therefore acid catalyst is not needed in order to progress the reaction

<ul><li><p>forms an ester (and HCl)</p></li><li><p>Same reaction as with a carboxylic acid (acyl chloride used in place of acid) </p></li><li><p>However - acyl chlorides are more reactive than carboxylic acids, therefore acid catalyst is not needed in order to progress the reaction </p></li></ul>
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Reaction of acyl chlorides with ammonia:

  • forms an amide (and HCl / NH4Cl)

<ul><li><p>forms an amide (and HCl / NH4Cl)</p></li></ul>
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Reaction of acyl chlorides with amines:

  • forms an amide (secondary or tertiary) (and HCl)

<ul><li><p>forms an amide (secondary or tertiary) (and HCl)</p></li></ul><p></p>
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Summary of reactions of acyl chlorides:

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