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    Carbonyl Compounds

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    Carbonyl Compounds

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    18. Carbonyl Compounds

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    Carbonyl Compounds

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    of 5

    CIE Chemistry A Level

    18 : Carbonyl Compounds
    Notes

    www.pmt.education
    Aldehydes and Ketones

    Aldehydes​ and ​ketones​ both contain the carbonyl group,


    C=O.
    The​ position​ of the ​carbonyl​ group in the carbon chain is
    different​ in aldehydes and ketones.

    The carbonyl group is at the end of the carbon chain in


    aldehydes and in the middle in ketones. The suffix for
    aldehydes is ​-al​ and the suffix for ketones is ​-one​.

    Formation of aldehydes and ketones


    Aldehydes and ketones are formed when alcohols are
    oxidised​ using ​acidified potassium dichromate(VI)
    (Cr​2​O​7​2-​/H​+​).

    Aldehydes are formed from ​primary​ alcohols, whereas ketones are formed from ​secondary
    alcohols.

    Primary alcohols
    Primary​ alcohols can be ​partially oxidised​ to ​aldehydes​.
    CH​3​CH​2​OH + [O] → CH​3​CHO + H​2​O
    If the aldehyde undergoes ​further oxidation​, ​carboxylic acids ​are produced.
    CH​3​CHO + [O] → CH​3​COOH + H​2​O
    The full oxidation reaction can be written as:
    CH​3​CH​2​OH + 2[O] → CH​3​COOH + 2H​2​O
    If you are only collecting the aldehyde, carry out the reaction with excess alcohol and distill off the
    aldehyde as soon as it forms to prevent further oxidation.

    Secondary alcohols
    Secondary​ alcohols are oxidised to ​ketones​. No further oxidation can take place.
    CH​3​C(OH)HCH​3​ + [O] → CH​3​COCH​3​ + H​2​O

    Reduction of aldehydes and ketones


    A ​reducing agent​ can be used to reverse the reactions above and convert aldehydes and ketones
    back to primary and secondary alcohols.
    Typically LiAlH​4 or
    ​ NaBH​4​ (dissolved in water with methanol) are used as reducing agents for this
    reaction.

    www.pmt.education
    Reduction of aldehydes
    RCHO + 2[H] →RCH​2​OH
    For example, the reduction of ​ethanal to ethanol​:

    Reduction of ketones
    R​1​COR​2​ + 2[H] →RC(OH)HR​2

    For example, the reduction of ​propanone to propanal​:

    Reaction with HCN and KCN or NaCN


    Hydrogen cyanide reacts with aldehydes and ketones to produce ​hydroxynitrile compounds​ by
    removing the C=O double bond. The reaction is called ​nucleophilic addition​ (see the mechanism
    on the following page).

    Naming:
    When naming a hydroxynitrile, the ​carbon in the nitrile group (C≡N) ​is referred to as the​ first
    carbon​ so the position of groups (including the alcohol group) is counted from there. In the
    equations below, the product of the first reaction is ​2-hydroxypropanenitrile​ and the product of
    the second reaction is ​2-hydroxy-2-methylpropanenitrile​.

    HCN is a very ​poisonous gas. ​Often ​KCN​ or ​NaCN​ are used with acid instead to form HCN in
    situ.

    www.pmt.education
    Nucleophilic addition reactions
    When aldehydes and ketones react with HCN to form ​hydroxynitriles​, a​ nucleophilic addition
    reaction occurs.

    A nucleophile is an​ electron pair donor​.

    The mechanism:
    The ​carbonyl bond​ (C=O) is ​highly polar​. The negative​ cyanide ion​ acts as a ​nucleophile​ and
    attacks the slightly positive carbon atom. The C=O bond breaks, leaving only a ​single bond
    between the ​carbon and oxygen ​atoms.
    The negatively charged oxygen then bonds to a ​hydrogen ion​ (from HCN or any added acid).

    Detecting carbonyl compound


    The carbonyl group can be detected using 2,4-dinitrophenylhydrazine (2,4-DNPH).
    When 2,4-DNPH is added to a solution of aldehyde or ketone, a ​yellow/ orange precipitate​ is
    produced. The formation of this coloured precipitate indicates the presence of a​ C=O carbonyl
    group​.

    Distinguishing between aldehydes and ketones


    Simple tests can be carried out to detect whether a compound is an aldehyde or a ketone.
    Ketones​ are ​not easily oxidised​ whereas ​aldehydes​ are ​easily oxidised​ to carboxylic acids.

    After identifying a solution as a carbonyl using 2,4-DNPH, certain reactions can be carried out
    using ​oxidising agents​. A ​positive result​ indicates that an ​aldehyde​ is present while a ​negative
    result​ suggests a ​ketone ​is present.

    Acidified potassium dichromate(VI)


    Aldehyde​ - orange solution turns green.
    Ketone​ - no visible change / solution remains orange.

    Tollen’s reagent
    Aldehyde​ - silver mirror forms on the walls of the test tube.
    Ketone​ - no visible change.

    Fehling’s reagent
    Aldehyde​ - blue solution gives a brick red precipitate.
    Ketone​ - no visible change / solution remains blue.

    www.pmt.education
    Deducing the presence of CH​3​CO- group
    A CH​3​CO- group can be detected using ​alkaline aqueous iodine,​ I​2​.
    Iodine​ is added to the carbonyl, followed by ​sodium hydroxide​ (to make the solution alkaline). If
    the CH​3​CO- group is present, a ​yellow precipitate​ of ​tri-iodomethane​ (CHI​3​) will form.
    CH​3​COR + 3I​2​ + 4NaOH → RCOONa + CHI​3​ + 3NaI + 3H​2​O

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