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    Phenol: A Guide For CAPE Students

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    Jordan Steele
    Phenol is a weak acid that dissolves slightly in water to form a weak acidic solution. It is a stronger acid than aliphatic alcohols due to the aromatic ring stabilizing the resulting anion. Phenol reacts with sodium hydroxide to form a salt, sodium phenoxide, and it reacts with bromine water without a catalyst to undergo electrophilic substitution at the 2, 4, and 6 positions on the aromatic ring. Relative acidities increase in the order of ethanol, water, and then phenol based on the stability of their anions.

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    Phenol: A Guide For CAPE Students

    Uploaded by

    Jordan Steele
    55 views11 pages
    Phenol is a weak acid that dissolves slightly in water to form a weak acidic solution. It is a stronger acid than aliphatic alcohols due to the aromatic ring stabilizing the resulting anion. Phenol reacts with sodium hydroxide to form a salt, sodium phenoxide, and it reacts with bromine water without a catalyst to undergo electrophilic substitution at the 2, 4, and 6 positions on the aromatic ring. Relative acidities increase in the order of ethanol, water, and then phenol based on the stability of their anions.

    Original Description:

    Cape unit 2 chemistry phenols

    Original Title

    Phenols in CAPE Unit 2

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    Phenol is a weak acid that dissolves slightly in water to form a weak acidic solution. It is a stronger acid than aliphatic alcohols due to the aromatic ring stabilizing the resulting anion. Phenol reacts with sodium hydroxide to form a salt, sodium phenoxide, and it reacts with bromine water without a catalyst to undergo electrophilic substitution at the 2, 4, and 6 positions on the aromatic ring. Relative acidities increase in the order of ethanol, water, and then phenol based on the stability of their anions.

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    55 views11 pages

    Phenol: A Guide For CAPE Students

    Uploaded by

    Jordan Steele
    Phenol is a weak acid that dissolves slightly in water to form a weak acidic solution. It is a stronger acid than aliphatic alcohols due to the aromatic ring stabilizing the resulting anion. Phenol reacts with sodium hydroxide to form a salt, sodium phenoxide, and it reacts with bromine water without a catalyst to undergo electrophilic substitution at the 2, 4, and 6 positions on the aromatic ring. Relative acidities increase in the order of ethanol, water, and then phenol based on the stability of their anions.

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    of 11

    PHENOL

    A guide for CAPE students

    2015
    SPECIFICATIONS
    PHENOL - REACTIONS OF THE OH GROUP

    Water phenol is a weak acid


    it dissolves very slightly in water to form a weak acidic solution
    it is a stronger acid than aliphatic alcohols
    the ring helps weaken the O-H bond and stabilises the resulting anion

    C6H5OH(aq) C6H5O¯(aq) + H+(aq)

    NaOH phenol reacts with sodium hydroxide to form a salt - sodium phenoxide
    it is ionic and water soluble

    C6H5OH(aq) + NaOH(aq) ——> C6H5O¯ Na+(aq) + H2O(l)

    Sodium phenol reacts with sodium to form an ionic salt - sodium phenoxide
    hydrogen is also produced
    this reaction is similar to that with aliphatic alcohols such as ethanol

    2C6H5OH(s) + 2Na(s) ——> 2C6H5O¯ Na+(s) + H2(g)


    2.Reaction with an acyl chloride like ethanoyl chloride

    Phenol reacts with ethanoyl chloride at room


    temperature. Phenyl ethanoate is formed together
    with hydrogen chloride gas.
    3.Reaction with sodium hydroxide (note
    that aliphatic alcohols do NOT react with
    sodium hydroxide)

    Phenols are more acidic than alcohols and thus can


    react with strong bases like sodium hydroxide.
    PHENOL - REACTIONS OF THE AROMATIC RING

    ELECTROPHILIC SUBSTITUTION

    Bromine the OH group is electron releasing


    it increases the electron density of the delocalised system
    it makes substitution much easier compared to benzene
    the electron density is greatest at the 2,4 and 6 positions
    substitution takes place at the 2,4 and 6 positions
    phenol reacts readily with bromine water WITHOUT A CATALYST
    it is so easy that multiple substitution takes place
    other electrophiles such as NO2+ react in a similar way
    1. Reaction with brominePHENOLS
    water
    A white ppt is immediately formed
    when
    bromine water is added to a solution of
    phenol in water. The bromine water
    decolorises. The ppt has an antiseptic
    smells of
    .
    Relative acidities of Alcohols, Water and Phenols

    Both ethanol and phenol dissociate into their


    ethoxide and phenoxide ion respectively and
    release a proton when dissolved in water
    therefore both substances can act as acids.
    However they have varying orders of acidity,
    in fact increasing order of acidity is ethanol,
    water and then phenol.
    The strength as an acid depends on the stability of the anion formed

    The greater the charge spread over the ion, the more stable
    the ion is and the more readily it is formed. The more
    stable the anion, the more readily it is formed i.e. the more
    readily a proton is donated i.e. the stronger the acid.

    pKa values can be used to express acidity of molecules


    The smaller the value, the more acidic the substance is:
    Ethanol pKa = 16.0, Water pKa = 15.7, Phenol pKa = 10.0
    REVISION CHECK
    What should you be able to do?

    Recall and explain the physical properties of alcohols


    Recall the different structural types of alcohols
    Recall the Lewis base properties of alcohols
    Recall and explain the chemical reactions of alcohols
    Write balanced equations representing any reactions in the section
    Understand how oxidation is affected by structure
    Recall how conditions and apparatus influence the products of oxidation
    Explain how infrared spectroscopy can be used to differentiate between functional groups

    CAN YOU DO ALL OF THESE? YES NO


    You need to go over the
    relevant topic(s) again
    Click on the button to
    return to the menu
    WELL DONE!
    Try some past paper questions

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