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    Carboxylic Acids and Esters

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    Carboxylic Acids and Esters

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    5 views18 pages

    Carboxylic Acids and Esters

    Uploaded by

    csharpest13

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
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    LEARNING OBJECTIVES

    • Know that carboxylic acids contain the functional group –COOH

    • Understand how to draw structural and displayed formulae for unbranched-chain


    carboxylic acids with up to four carbon atoms in the molecule, and name
    each compound.

    • Describe the reactions of aqueous solutions of carboxylic acids with metals and
    metal carbonates.

    • Know that vinegar is an aqueous solution containing ethanoic acid.


    The carboxylic acids form another homologous series, this time with the general formula CnH2n+1COOH. All
    the carboxylic acids possess –COOH as their functional group. The functional group is also called the carboxyl
    group.
    The first member of the carboxylic acid family is methanoic acid (HCOOH), which is found in stinging ants and
    nettles.
    • The ending ‘e’ of the corresponding alkane name for the carbon chain is replaced with ‘oic’ and
    the word ‘acid’ is added.
    • The carbon atom of the –COOH functional group is counted as part of the carbon chain. It
    is counted as the first carbon.
    • Any substituent on the carbon chain is named as usual.

    Methanoic acid Ethanoic acid 2-methylpropanoic acid


    Carboxylic acids reacting as acids
    Methanoic acid is present in stinging nettles and ant stings. Ethanoic acid, however, is the most well known as it
    is the main constituent of vinegar.
    Like other acids, ethanoic acid affects indicators and will react with metals such as magnesium. However,
    whereas the mineral acids, such as hydrochloric acid, are called strong acids, ethanoic acid is a weak
    acid.
    Even though it is a weak acid, it will still undergo typical reactions of acids.

     Ethanoic acid will react with bases to form salts.


    Ethanoic acid + sodium hydroxide sodium ethanoate + water

    CH3COOH + NaOH CH3COONa + H2O

    Ethanoic acid will react with reactive metals such as magnesium to give a salt and hydrogen
    gas. Ethanoic acid + magnesium magnesium ethanoate + hydrogen

    2CH3COOH + Mg (CH3COO)2Mg + H2
    Carboxylic acids reacting as acids
     Ethanoic acid reacts with carbonates such as calcium carbonate to give calcium ethanoate, carbon dioxide
    and water.
    Ethanoic acid + calcium carbonate calcium ethanoate + carbon dioxide + water
    2CH3COOH + CaCO3 (CH3COO)2Ca + CO2 + H2O
    Formation of ethanoic acid by oxidation of ethanol
     By fermentation: When ethanol is left standing in air, bacteria (Acetobacter) bring about its oxidation to ethanoic
    acid.
     Using oxidising agents: Ethanol is oxidised much faster by warming it with the powerful oxidising
    agent
    potassium manganate(VII), in the presence of acid. This is achieved by refluxing.

    Ethanol + oxygen (from oxidising agent) ethanoic acid + water


    C2H5OH + 2[O] CH3COOH + H2O

    Refluxing: a technique using a condenser fitted vertically


    to condense vapours from an experiment back into a flask.
    Describe the reaction that takes place between ethanoic acid
    and:
    i. Calcium
    ii.potassium
    carbonate iii.potassium
    hydroxide.
    In each case, write a word equation as well as a balanced
    chemical equation.
    ESTERS
    • Describe the reaction of a carboxylic acid with an alcohol
    using an acid catalyst to form an ester.
    Esterification
    Esterification is a chemical reaction between an alcohol and a carboxylic acid that produces an ester.
    Ethanoic acid will react with ethanol, in the presence of a few drops of concentrated sulfuric acid acting as a catalyst,
    to produce ethyl ethanoate – an ester.

    The esters formed usually have sweet, fruity


    smells. They are present naturally in fruits,
    and we use them in artificial flavourings
    and perfumes. They are also used as
    solvents, e.g. in nail varnish remover.
    Esterification
    Let’s take a look at the reaction between propanol and ethanoic
    acid.

    • Two molecules have joined to make a larger molecule, with the loss of a small molecule, water. So this is called a
    condensation reaction.
    • The reaction is reversible, and sulfuric acid acts a catalyst.
    Esterification
    Esterification
    Members of the ‘ester’ family have strong and pleasant smells.
    Esters are named after the acid and alcohol from which they are
    derived:
     name – alcohol part first, acid part second
     formula – acid part first, alcohol part second (or vice versa)

    Ethyl ethanoate Propyl methanoate Methyl butanoate


    Esterification

    Take note!
    An ester can be drawn either way round but the name is always written the same way round:
    ethyl ethanoate.

    Different ways of drawing ethyl ethanoate.


    Esterification

    Splitting an ester.
    You also need to be able to reverse this and work out which carboxylic acid and alcohol you
    would have to react together to produce a given ester. To do this, break apart the molecule
    between the C and O and add OH to one side and H to the other so that you have two OH groups.
    Questions

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