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    Carboxylic Acids

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    Tom Tommma
    Carboxylic acids can be produced through two main methods: oxidation of alcohols via fermentation or using strong oxidizing agents. Fermentation of ethanol by acetic acid bacteria produces ethanoic acid/vinegar, while heating ethanol with acidified potassium manganate(VII) also yields ethanoic acid. Carboxylic acids are weak acids that form salts with metals and react with carbonates to produce salts, water and carbon dioxide. They undergo esterification reactions with alcohols to form esters, with sulfuric acid as a catalyst.

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    Carboxylic Acids

    Uploaded by

    Tom Tommma
    26 views7 pages
    Carboxylic acids can be produced through two main methods: oxidation of alcohols via fermentation or using strong oxidizing agents. Fermentation of ethanol by acetic acid bacteria produces ethanoic acid/vinegar, while heating ethanol with acidified potassium manganate(VII) also yields ethanoic acid. Carboxylic acids are weak acids that form salts with metals and react with carbonates to produce salts, water and carbon dioxide. They undergo esterification reactions with alcohols to form esters, with sulfuric acid as a catalyst.

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    Carboxylic acids can be produced through two main methods: oxidation of alcohols via fermentation or using strong oxidizing agents. Fermentation of ethanol by acetic acid bacteria produces ethanoic acid/vinegar, while heating ethanol with acidified potassium manganate(VII) also yields ethanoic acid. Carboxylic acids are weak acids that form salts with metals and react with carbonates to produce salts, water and carbon dioxide. They undergo esterification reactions with alcohols to form esters, with sulfuric acid as a catalyst.

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    © All Rights Reserved
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    Download as pdf or txt
    26 views7 pages

    Carboxylic Acids

    Uploaded by

    Tom Tommma
    Carboxylic acids can be produced through two main methods: oxidation of alcohols via fermentation or using strong oxidizing agents. Fermentation of ethanol by acetic acid bacteria produces ethanoic acid/vinegar, while heating ethanol with acidified potassium manganate(VII) also yields ethanoic acid. Carboxylic acids are weak acids that form salts with metals and react with carbonates to produce salts, water and carbon dioxide. They undergo esterification reactions with alcohols to form esters, with sulfuric acid as a catalyst.

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    Carboxylic Acids: Basics

    • These are a homologous series of organic compounds that all contain the same
    functional group: –COOH
    • They have the general formula: CnH2n+1COOH
    • They are colourless liquids which are weakly acidic and have typical acidic
    properties
    • They react with alkaline solutions, turn blue litmus red and
    form salts called ethanoates

    Making Carboxylic Acids

    • Two methods used to make carboxylic acids are:


    o Oxidation by fermentation
    o Using oxidising agents
    • The microbial oxidation (fermentation) of ethanol will produce a weak solution of
    vinegar (ethanoic acid)
    • This occurs when a bottle of wine is opened as bacteria in the air (acetobacter) will use
    atmospheric oxygen from air to oxidise the ethanol in the wine

    C2H5OH (aq) + O2 (g) → CH3COOH (aq)+ H2O (l)

    • The acidic, vinegary taste of wine which has been left open for several days is due to
    the presence of ethanoic acid
    • Alternatively, oxidising agent potassium manganate(VII) can be used
    • This involves heating ethanol with acidified potassium manganate(VII) in the
    presence of an acid
    • The heating is performed under reflux which involves heating the reaction mixture in a
    vessel with a condenser attached to the top
    • The condenser prevents the volatile alcohol from escaping the reaction vessel as
    alcohols have low boiling points
    • The equation for the reaction is:

    CH3CH2OH (aq) + [O] → CH3COOH (aq) + H2O (l)


    • The solution will change from purple to colourless
    • The oxidising agent is represented by the symbol for oxygen in square brackets

    Diagram showing the


    experimental setup for the oxidation with KMnO4 using reflux apparatus
    Chemical properties of carboxylic acid.
    • Carboxylic acids are weak acids and dissociate slightly in water, producing a mildly
    acidic solution
    • The equilibrium lies far to the left during ionisation:

    CH3COOH (aq) ⇌ H+ (aq) + CH3COO- (aq)

    • The carboxylic acids behave like other acids


    • They react with metals to form a salt and hydrogen and with carbonates to form a
    salt, water and carbon dioxide gas
    • They also take part in neutralisation reactions with bases to produce salt and water

    Reaction of reactive metals and carboxylic acids

    In the reaction with metals a metal salt and hydrogen gas are produced

    o For example, in reaction with magnesium the salt magnesium ethanoate is


    formed:

    2CH3COOH (aq) + Mg (s) → (CH3COO)2Mg (aq) + H2(g)

    Reaction of bases with carboxylic acids

    In the reaction with hydroxides a salt and water are formed in a neutralisation reaction

    For example, in reaction with potassium hydroxide the salt potassium ethanoate is formed:

    CH3COOH (aq) + KOH (aq) → CH3COOK (aq) + H2O (l)

    Reaction of metal carbonates with carboxylic acid

    In the reaction with carbonates a salt, water and carbon dioxide gas are produced

    For example, in reaction with potassium carbonate the salt potassium ethanoate is formed:

    2CH3COOH (aq) + K2CO3 (s) → 2CH3COOK (aq) + H2O (l) +CO2 (g)
    Esterification

    • Alcohols and carboxylic acids react to make esters in esterification reactions


    • Esters are compounds with the functional group R-COO-R
    • Esters are sweet-smelling oily liquids used in food flavourings and perfumes
    • Ethanoic acid will react with ethanol in the presence of concentrated sulfuric acid
    (catalyst) to form ethyl ethanoate:

    CH3COOH (aq) + C2H5OH (aq) ⇌ CH3COOC2H5 (aq) + H2O (l)

    Diagram showing the formation of ethyl ethanoate


    Naming Esters

    • An ester is made from an alcohol and carboxylic acid


    • The first part of the name indicates the length of the carbon chain in the alcohol, and it
    ends with the letters ‘- yl’
    • The second part of the name indicates the length of the carbon chain in the carboxylic
    acid, and it ends with the letters ‘- oate’
    o E.g. the ester formed from pentanol and butanoic acid is
    called pentyl butanoate

    Diagram showing the origin of each carbon chain in ester; this ester is ethyl
    butanoate

    Table showing the formation of esters

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