Carboxylic Acids: Intro + Physical properties

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Last updated 5:56 AM on 4/22/26
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7 Terms

1
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general structure of carboxylic acids

  • contains the carboxyl group (-CO2H)

  • trigonal planar about the carboxyl carbon (bond angle=120)

  • carbonyl carbon is sp2 hybridised

<ul><li><p>contains the carboxyl group (-CO<sub>2</sub>H)</p></li><li><p>trigonal planar about the carboxyl carbon (bond angle=120)</p></li><li><p>carbonyl carbon is sp<sup>2</sup> hybridised</p></li></ul><p></p>
2
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nomenclature for carboxylic acids

carbon bonded to

  • straight chain: suffix ‘-oic acid’ eg methanoic acid

  • -CO2H bonded to the ring: suffix ‘carboxylic acid’ eg cyclopentane carboxylic acid

  • -CO2H bonded to aromatic ring: suffix ‘benzoic acid’

  • carbon in ring attached to -CO2H is numbered C1

3
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Arrange in increasing boiling point

  • carboxlic acids

  • hydrocarbons

  • aldehydes and ketones

  • alcohols and phenols

hydrocarbons> alcohols and phenols > aldehydes and ketones > carboxylic acids

4
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Why do carboxylic acids have higher bp than alcohols with similar electron clouds size?

  1. Carboxylic acids dimerise with hydrogen bonding

  • effectively doubling their electron cloud size in the dimer

  • stronger dispersion forces between carboxylic acid molecules

  1. electron-withdrawing C=O group intensifies the partial positive charge on the H atom,

  • stronger hydrogen bonding between carboxylic acid molecules

  • more energy required to overcome the stronger dispersion forces and hydrogen bonding than for alcohol

<ol><li><p>Carboxylic acids dimerise with hydrogen bonding</p></li></ol><ul><li><p>effectively doubling their electron cloud size in the dimer</p></li><li><p>stronger dispersion forces between carboxylic acid molecules </p></li></ul><p></p><ol start="2"><li><p>electron-withdrawing C=O group intensifies the partial positive charge on the H atom,</p></li></ol><ul><li><p>stronger hydrogen bonding between carboxylic acid molecules </p></li></ul><p></p><ul><li><p>more energy required to overcome the stronger dispersion forces and hydrogen bonding than for alcohol</p></li></ul><p></p>
5
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Which type of carboxylic acids are highly soluble in non-polar solvents and why?

  • carboxylic acids with long carbon chains

  • can form hydrogen-bonded dimers and increase size of e- cloud, therefore strength of dispersion forces

  • energy released from stronger dispersion forces between hydorcarbon chain of dimers and solvent molecules

  • is able to overcome the dispersion forces and hydrogen bonding in carboxylic acid and hydrogen bonding in water

6
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Which type of carboxylic acids are highly soluble in water/polar solvents and why?

  • carboxylic acids with shorter hydrocarbon chains

  • cannot form hydrogen-bonded dimers

  • instead, form hydrogen bonds with water

  • energy released form forming of hydrogen bonds between carboxylic acid molecules and water moleculesbetween -CO2H group and water molecules

  • is more than energy required to overcome weaker dispersion forces between carboxylic acid molecules and hydrogen bonding in water

7
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As length of hydrocarbon chain of carboxylic acid inceases, solubility in water increases/decreases?

  • as hydrocarbon chain length increases

  • stregnth of dispersion forces between carboxylic acid molecules inceases

  • energy released from hydrogen bonding between -CO2H group and water molecules

  • is less than energy needed to overcome stronger dispersion forces between carboxylic acid molecules and hydrogen bonding between water molecules