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CARBOXYLIC ACIDS – chemistry & uses

See also 10b. ESTERS – chemistry and uses (now on a separate page)

Doc Brown's GCSE/IGCSE/O Level KS4 science–CHEMISTRY Revision Notes

Oil, useful products, environmental problems, introduction to organic chemistry

10a. Carboxylic Acids – structure, properties and uses

Carboxylic acids are a group of organic compounds which have weakly acidic properties. Carboxylic acids react with bases/alkalis to for salts and release carbon dioxide from carbonates. They react with alcohols to form esters

Index of KS4 Science GCSE/IGCSE/O Level Chemistry Oil & Organic Chemistry revision notes pages: 1. Fossil Fuels & carbon Cycle : 2. Fractional distillation of crude oil & physical properties and uses of fractions, what makes a good fuel? : 3. ALKANES - saturated hydrocarbons, structure, uses, combustion : 4. Pollution, carbon monoxide, sulfur/nitrogen oxides, climate change-global warming : 5. Alkenes - unsaturated hydrocarbons, structure and chemistry : 6. Cracking - a problem of supply and demand, other products : 7. Polymers, plastics, uses and problems : 8. Introduction to Organic Chemistry - Why so many series of organic compounds? : 9a. Alcohols, Ethanol, manufacture, physical properties & chemical reactions : 9b. Biofuels & alternative fuels, hydrogen, biogas, biodiesel : 10a. Carboxylic acids - chemistry and uses : 10b. Esters, chemistry and uses including perfumes : 11. Condensation polymers, Nylon & Terylene, comparing thermoplastics, fibres and thermosets : 12. Natural Molecules - carbohydrates - sugars - starch : 13. Amino acids, proteins, enzymes & chromatography : 14. Oils, fats, margarine and soaps : 15. Vitamins, drugs-analgesic medicines & food additives and aspects of cooking chemistry! : 16. Ozone destruction, CFC's and free radicals : 17. Extra notes, ideas and links on Global Warming and Climate Change : Multiple Choice and Gap-Fill Quizzes: m/c QUIZ on Oil Products (GCSE/IGCSE easier-foundation-level) : m/c QUIZ on Oil Products (GCSE/IGCSE harder-higher-level) : IGCSE/GCSE m/c QUIZ on other Aspects of Organic Chemistry : and 3 Easy linked GCSE/IGCSE Oil Products word-fill worksheets

ALL my Advanced Level Organic Chemistry revision notes

10a. CARBOXYLIC ACIDS

We find members of the homologous series called carboxylic acids in fruits and in vinegar and many in fragrances and food additives as carboxylic acid derivatives called esters.

  • The molecular structure of carboxylic acids
  • Carboxylic acids form another homologous series and have the functional group –COOH.
    • A homologous series is a family of compounds which have the same general formula and have a similar molecular structure and similar chemical properties because they have the same functional group of atoms (e.g. in this case the COOH group).
    • The homologous series of carboxylic acids have the general formula CnH2n+1COOH, where n = 0, 1, 2 etc. number of carbon atoms in the molecule minus 1.
    • The functional group (COOH) is a group atoms common to all members of a homologous series that confer a particular set of characteristic chemical reactions on each member of the series e.g. in this series they all behave like acids with alkalis, carbonates etc., they all form compounds called esters when reacted with alcohols.
    • Members of a  homologous series have similar physical properties such as appearance, melting/boiling points, solubility etc. BUT show trends in them e.g. steady increase in melting/boiling point with increase in carbon number or molecular mass.
  • The structures of the first three members of the carboxylic acid homologous series are shown given below.
  • The last alcohol structure given below is the full displayed formula which you should definitely know, but you also need to know the various abbreviated ways of writing the molecular structure of alcohols.
  • Names end in ...oic acid (actually here they all end in ..anoic acid),
    • and check out their formula from the general formula above, the final structure is the full displayed formula showing every covalent bond in the molecule (C–H, C=O, C–O, O–H, C–C) and note the arrangement of atoms in the COOH functional group, common to all the members of the homologous series of carboxylic acids. The first three are as follows ...
    • methanoic acid (old name 'formic acid')
      • or or , 1st in the series
    • ethanoic acid (old name 'acetic acid', in vinegar)
      • C2H5COOH or or or , 2nd in the series
    • propanoic acid (old name 'propionic acid')
      • or or , 3rd in the series etc.
    • ADVANCED A Level revision notes on the structure and naming of CARBOXYLIC ACIDS and DERIVATIVES, including nomenclature of isomers (NOT needed for GCSE/IGCSE students!)
  • The properties and uses of carboxylic acids
    • This particular homologous series of carboxylic acids are colourless liquids with very strong odours (pungent smell) and tastes.
    • The obnoxious smell of rancid butter and sweaty socks are due to the formation of carboxylic acids.
    • It should be mentioned here that carboxylic acids with long carbon chains are called fatty acids, because they are combined with an alcohol called glycerol to form large ester molecules (glycerides/triesters) that make up most natural oils from plants and fat in animals.
      • Many traditional soaps are made from natural oils and fats.
      • The fatty acids may be saturated (no C=C double bonds) or unsaturated (with at leat one C=C double bond) in the carbon chain.
      • For more details on glycerides and soaps see Oils, fats, margarine and soaps
  • Vinegar contains ethanoic acid (old name 'acetic acid')
    • In the chemical industry ethanoic acid can be manufactured on a large scale by oxidising the alcohol ethanol.
    • See in section 9 Oxidation of the alcohol ethanol
    • It is used as a food preservative and in food flavourings.
    • It is the oxidation of ethanol to ethanoic acid that results in alcoholic drinks turning sour (e.g. cider, wine) when exposed to air.
    • The fruit material already contains the enzymes that catalyse the oxidation of ethanol ('alcohol') in the presence of air.
    • ethanol + oxygen ==> ethanoic acid + water
    • CH3CH2OH + O2 ==> CH3COOH + H2
    • + O2 ==>  + H2O
    • This reaction occurs if wine, beer or cider is left out open to the air, it eventually becomes vinegar and not very nice to drink!, but vinegar is very nice in salad dressings and on your fish and chips.
  • Ethanoic acid is used in the manufacture of the fibre, acetate rayon.
  • CITRIC ACIDCitrus fruits like oranges and lemons and many soft drinks contain the tri–carboxylic acid citric acid. and contribute to the 'tarter' or 'sour' taste of fruit. The molecule contains three acidic carboxylic acid groups –COOH.
    • Citric acid is a natural preservative (E330 on food labels) and is found in the largest quantities in oranges, lemons, limes and grapefruit. It is an anti–oxidant. Metal salts from citric acid, i.e. citrates, are used in dietary supplements to deliver trace metal minerals in a biologically available/absorbable chemical form.
    • Citric acid can be used in baking powder to react with sodium bicarbonate giving the raising action from carbon dioxide gas formation. The same combination can be used to give the fizzy drink effect in medicines like ant–acid stomach powders.
    • Citric acid is made in large quantities for the food industry, including fizzy drinks – which can be quite acid – dental concerns about the health of teeth here!
    • Citric acid is strong enough to be used in some limescale removers – so think about your teeth when consuming all those fizzy drinks we might like!
  • Aspirin is a carboxylic acid. Aspirin is a drug used for pain relief and is taken regularly by those at risk from heart attacks (see also Drugs).
  • Ascorbic acid (vitamin C) is another carboxylic acid and is present in fresh fruit and vegetables and is vital for good health AND the body cannot synthesise it, so you must eat fruit and vegetables regularly!
    • A lack of vitamin C can cause the disease scurvy. The symptoms of scurvy are skin sores, spongy gums and bleeding from mucous membranes. This is one example of malnutrition diseases caused by a vitamin deficiency in a diet.
  • Long chain carboxylic acids, known as 'fatty acids', are used to make soaps and detergents, originally derived from plant oils.
    • Below are some diagrams of the organic molecules or ions involved, typically with 16 to 20 carbon atoms in the chain.
    • Diagram S1: The stearic acid molecule C17H35COOH or CH3(CH2)16COOH is a typical long chain fatty acid obtained from naturally occurring plant oils and used to make traditional soaps.
    • Diagram S2: The salt sodium stearate C17H35COONa+, formed when stearic acid is neutralised with sodium hydroxide is a typical soap molecule.
  • Carboxylic acids are weak acids
    • Typically weak acid solutions have a pH of around 2 to 6 (yellow–orange–pink with universal indicator), which is somewhat higher than strong acid solutions with a pH of 0 to 2.
    • Advanced Chemistry Page Index and LinksThey are called weak acids because only a few % of the molecules in aqueous ionise to release protons (hydrogen ions, H+).
      • It is the presence of hydrogen ions that makes aqueous solutions of carboxylic acids acid.
      • e.g. for ethanoic acid (vinegar)
      • 98% CH3COOH(aq) (c) doc b CH3COO(aq) + H+(aq)
      • This is a reversible reaction with only 2% of the weak acid ionised on the right–hand side of the equilibrium.
        • At similar concentrations, strong acids have a low pH of 0 or 1, because they are more fully ionised.
        • Ethanoic acid will turn blue litmus pink and universal indicator gives an orangey–red colour.
        • Being a weak acid, the pH is higher than in strong mineral acids like hydrochloric acid and the rate of reaction is slowed down too.
        • For a more detailed discussion of these points see The theory of acids and bases
    • Despite being a weak acid, carboxylic acids like ethanoic acid behave like any other acid and react with metals, alkalis and carbonate to form salts and fizzing here and there!
  • Carboxylic acids react with metals and are neutralised by bases/alkalis (insoluble or soluble metal oxides, hydroxides and carbonates) to form salts. The salt names depends on the name of the acid, so methanoic acids forms methanoate salts, ethanoic acid gives ethanoate salts, propanoic acid gives propanoate salts on neutralisation ...
    • metals react and dissolve to form salts and hydrogen e.g.
      • ethanoic acid + magnesium ==> magnesium ethanoate + hydrogen
      • 2CH3COOH + Mg ==> (CH3COO)2Mg + H2
    • alkalis (soluble bases) react to form a carboxylic acid salt and water  e.g.
      • ethanoic acid + sodium hydroxide ==> sodium ethanoate + water
      • CH3COOH + NaOH ==> CH3COONa + H2O
      • ethanoic acid + potassium hydroxide ==> potassium ethanoate + water
      • CH3COOH + KOH ==> CH3COOK + H2O
    • insoluble bases dissolve and react to form salt and water e.g.
      • zinc oxide + ethanoic acid ==> zinc ethanoate + water
      • ZnO + 2CH3COOH ==> (CH3COO)2Zn + H2O
      • ethanoic acid + calcium hydroxide ==> calcium ethanoate + water
      • 2CH3COOH + Ca(OH)2 ==> (CH3COO)2Ca + 2H2O
      • ethanoic acid + magnesium hydroxide ==> magnesium ethanoate + water
      • 2CH3COOH + Mg(OH)2 ==> (CH3COO)2Mg + 2H2O
    • carbonate and hydrogencarbonate bases produce a carboxylic acid salt, water and carbon dioxide gas e.g.
      • ethanoic acid + sodium hydrogen carbonate ==> sodium ethanoate + water + carbon dioxide
      • CH3COOH + NaHCO3 ==> CH3COONa + H2O + CO2
      • ethanoic acid + sodium carbonate ==> sodium ethanoate + water + carbon dioxide
      • 2CH3COOH + Na2CO3 ==> 2CH3COONa + H2O + CO2
      • propanoic acid + sodium carbonate ==> sodium propanoate + water + carbon dioxide
      • 2CH3CH2COOH + Na2CO3 ==> 2CH3CH2COONa + H2O + CO2
      • ethanoic acid + magnesium carbonate ==> magnesium ethanoate + water + carbon dioxide
      • 2CH3COOH + MgCO3  ==> (CH3COO)2Mg + H2O + CO2
      • ethanoic acid + calcium carbonate ==> calcium ethanoate + water + carbon dioxide
      • 2CH3COOH + CaCO3  ==> (CH3COO)2Ca + H2O + CO2
    • aqueous ammonia solution forms ammonium salts e.g.
      • methanoic acid + ammonia ==> ammonium methanoate
        • HCOOH + NH3 ==> HCOONH4
      • ethanoic acid + ammonia ==> ammonium ethanoate
        • CH3COOH + NH3 ==> CH3COONH4
      • Strictly speaking, ammonium hydroxide doesn't really exist, but in older texts you will find these reactions written in this way, but NOT correct e.g.
        • propanoic acid + ammonium hydroxide ==> ammonium propanoate + water
        • CH3CH2COOH + NH4OH ==> CH3CH2COONH4 + H2O
  • Advanced Chemistry Page Index and LinksESTERS: Carboxylic acids are used to manufacture esters.
    • Carboxylic acids react with alcohols to form members of another homologous series called esters. Concentrated sulphuric acid acts as a catalyst in this reaction.
    • General word equation: carboxylic acid + alcohol ==> ester + water
    • ethanoic acid + ethanol ethyl ethanoate + water
    • + + H2O
      • sometimes more simply written as
      • CH3COOH + CH3CH2OH CH3COOCH2CH3 + H2O
    • Detailed notes on esters are on a separate page now, and they are a very important group of compounds and more than merit their own page!

Advanced Chemistry Page Index and Links

 

Multiple Choice Quizzes and Worksheets

KS4 Science GCSE/IGCSE m/c QUIZ on Oil Products (easier–foundation–level)

KS4 Science GCSE/IGCSE m/c QUIZ on Oil Products (harder–higher–level)

KS4 Science GCSE/IGCSE m/c QUIZ on other aspects of Organic Chemistry

and (c) doc b 3 linked easy Oil Products gap–fill quiz worksheets

ALSO gap–fill ('word–fill') exercises originally written for ...

... AQA GCSE Science (c) doc b Useful products from crude oil AND (c) doc b Oil, Hydrocarbons & Cracking etc.

... OCR 21st C GCSE Science (c) doc b Worksheet gap–fill C1.1c Air pollutants etc ...

... Edexcel 360 GCSE Science Crude Oil and its Fractional distillation etc ...

... each set are interlinked, so clicking on one of the above leads to a sequence of several quizzes

ALL my Advanced Level Organic Chemistry revision notes

 

keywords equations: CH3CH2OH + O2 ==> CH3COOH + H2O


Revision notes on carboxylic acids reactions uses KS4 Science GCSE/IGCSE/O level Chemistry Information on carboxylic acids reactions uses for revising for AQA GCSE Science, Edexcel Science chemistry IGCSE Chemistry notes on carboxylic acids reactions uses OCR 21st Century Science, OCR Gateway Science notes on carboxylic acids reactions uses WJEC gcse science chemistry notes on carboxylic acids reactions uses CIE O Level chemistry CIE IGCSE chemistry notes on carboxylic acids reactions uses CCEA/CEA gcse science chemistry (help for courses equal to US grade 8, grade 9 grade 10) science chemistry courses revision guides explanation chemical equations for carboxylic acids reactions uses educational videos on carboxylic acids reactions uses guidebooks for revising carboxylic acids reactions uses textbooks on carboxylic acids reactions uses

Advanced Chemistry Page Index and Links
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