Chapter 26.4 - Carboxylic Acid Derivatives {part 1}

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26.4 - Carboxylic acid derivates [ part 1] Key Facts: Notes! Carboxylic acid derivatives : - compounds than can be hydrolysed to form the parent carboxylic acid [OH in -COOH is replaced] R 0 11 C OH R O derivatives derivatives au have the acul group in their structure OR ester in hydrolysis this bond ✓ breaks in the presence of X H₂0 0 acyl C Chloride 11 CL R NH₂ amide R 0 acid anhydride - Suffic= -oyl chloride - parent chain recognise acyl Chloride functional group prepare in fume cupboard acyl chlorides e.g. H3C OH ethanoic acid 0 11 CH3CH₂-C preparation of acul chlorides ● - can be prepared from carboxylic acids with thionyl chloride, SOCI₂ |e.g. OH propanoic acid + SOCI ₂ 0 11 H3C CL ethanoul chloride → =0 CH3CH₂-C propanoy! Chloride CL + SO₂ + HCL 1 toxic gases hydrogen Chloride gas Condensation reaction: - two molecules react together to form larger molecules -Chlorine leaves 'elimination reaction of acyl chlorides -acyl chlorides are very reactive - easily converted into carboxylic acid derivatives such as esters / amides. they react with nucleophiles by losing CL whilst retaining C=0 double bond don't need fuu mechanim. (no curly arrow) reaction of acyl chlorides with alcohols and phenols to form esters e.g. CH3CH₂-C + HO-CH₂ CH3 CL ethano propanoyl chloride e.g. CH3CH₂-C 20 `CL CH3CH₂-C + OH phenor (not an alcohor) OCH₂CH3 ethylpropanoate + CH3CH₂-C phenyl Propanoate gas HCl + HCL reaction of acyl chlorides with water to form carboxylic acids -acyl chlorides will react violently with water to form a carboxylic acid, HCI (9) 40 CH3CH₂-C `CL propanoul chloride + H₂0 >> CH3CH₂ 20 1/1 ·C ОН propanoic acid Observation -dense steamy fumes - therefore must be done in annydrous conditions (without water) + Ha reaction acyl chlorides with ammoniq and amines to form amides. e.g. (HO 0 acid anhydrides H3C e.g. without water - loss of water ethanoic anhydride CH3 OCH derives from ال OH H3C ethanoic acid H₂C OH HO CH3 2 molecules of ethanoic acid i i ethanoic propanoic anhydride reactions of acid anhydrides Moto HO- phenol H₂C CH3 ethanoic anhydride phenyl ethanoate + ester - less reactive than acyl chlorides i i HỌCH,CH3 H₂C HO ethanoic acid carboxylic acid ·Sta + OCH₂CH₂ OH CH 3

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