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    Phenolistan

    Uploaded by

    guym4529
    It's about phenol production

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd

    Phenolistan

    Uploaded by

    guym4529
    3 views11 pages
    It's about phenol production

    Copyright

    © © All Rights Reserved

    Available Formats

    PPT, PDF, TXT or read online from Scribd

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    It's about phenol production

    Copyright:

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

    Phenolistan

    Uploaded by

    guym4529
    It's about phenol production

    Copyright:

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

    ROUTES

    TO PHENOL
    PHENOL

    Structure phenol is an aromatic alcohol with formula C6H5OH


    the OH group is attached directly to the benzene ring
    it is an almost colourless crystalline solid
    PHENOL

    Structure phenol is an aromatic alcohol with formula C6H5OH


    the OH group is attached directly to the benzene ring
    it is an almost colourless crystalline solid

    Preparation You cannot put an OH group directly onto a benzene ring by


    electrophilic substitution, so phenol has to be synthesised in
    a multi-stage process
    PHENOL

    Structure phenol is an aromatic alcohol with formula C6H5OH


    the OH group is attached directly to the benzene ring
    it is an almost colourless crystalline solid

    Preparation You cannot put an OH group directly onto a benzene ring by


    electrophilic substitution, so phenol has to be synthesised in
    a multi-stage process

    Step 1 - Nitration of benzene


    reagents conc. nitric acid and conc. sulphuric acid (catalyst)
    conditions reflux at 55°C
    equation C6H6 + HNO3 ——> C6H5NO2 + H2O
    mechanism electrophilic substitution
    PHENOL

    Structure phenol is an aromatic alcohol with formula C6H5OH


    the OH group is attached directly to the benzene ring
    it is an almost colourless crystalline solid

    Preparation You cannot put an OH group directly onto a benzene ring by


    electrophilic substitution, so phenol has to be synthesised in
    a multi-stage process

    Step 2 - Reduction of nitrobenzene


    reagents tin and conc. hydrochloric acid
    conditions reflux
    equation C6H5NO2 + 6 [H] ——> C6H5NH2 + 2H2O
    mechanism reduction
    PHENOL

    Structure phenol is an aromatic alcohol with formula C6H5OH


    the OH group is attached directly to the benzene ring
    it is an almost colourless crystalline solid

    Preparation You cannot put an OH group directly onto a benzene ring by


    electrophilic substitution, so phenol has to be synthesised in
    a multi-stage process

    Step 3 - Diazotisation of phenylamine


    reagents nitrous acid and hydrochloric acid (use sodium nitrite)
    conditions keep below 10°C
    equation C6H5NH2 + HNO2 + HCl ——> C6H5N2+ Cl¯ +
    2H2O
    reaction type diazotisation
    PHENOL

    Structure phenol is an aromatic alcohol with formula C6H5OH


    the OH group is attached directly to the benzene ring
    it is an almost colourless crystalline solid

    Preparation You cannot put an OH group directly onto a benzene ring by


    electrophilic substitution, so phenol has to be synthesised in
    a multi-stage process

    Step 4 - Substitution of diazo group by OH


    reagents water
    conditions warm above 10°C
    equation C6H5N2+ Cl¯ + H2O ——> C6H5OH + N2 +
    HCl
    reaction type hydrolysis / substitution
    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)


    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)


    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)

    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)


    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

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