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    Alcohols, Phenols and Ethers

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    Mike Daven Ladera
    The document summarizes experiments on the oxidation of alcohols, phenols, and ethers using various reagents such as potassium permanganate, chromic acid, and ferric chloride. It describes how primary, secondary, and tertiary alcohols react differently in oxidation reactions and confirmatory tests like the Lucas test. Phenol and substituted phenols are oxidized by potassium permanganate and bromine water. Their reactions with ferric chloride are also described. Guidelines for interpreting the results of the Lucas test are provided.

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    Alcohols, Phenols and Ethers

    Uploaded by

    Mike Daven Ladera
    22 views38 pages
    The document summarizes experiments on the oxidation of alcohols, phenols, and ethers using various reagents such as potassium permanganate, chromic acid, and ferric chloride. It describes how primary, secondary, and tertiary alcohols react differently in oxidation reactions and confirmatory tests like the Lucas test. Phenol and substituted phenols are oxidized by potassium permanganate and bromine water. Their reactions with ferric chloride are also described. Guidelines for interpreting the results of the Lucas test are provided.

    Original Title

    ALCOHOLS-PHENOLS-and-ETHERS

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    The document summarizes experiments on the oxidation of alcohols, phenols, and ethers using various reagents such as potassium permanganate, chromic acid, and ferric chloride. It describes how primary, secondary, and tertiary alcohols react differently in oxidation reactions and confirmatory tests like the Lucas test. Phenol and substituted phenols are oxidized by potassium permanganate and bromine water. Their reactions with ferric chloride are also described. Guidelines for interpreting the results of the Lucas test are provided.

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    22 views38 pages

    Alcohols, Phenols and Ethers

    Uploaded by

    Mike Daven Ladera
    The document summarizes experiments on the oxidation of alcohols, phenols, and ethers using various reagents such as potassium permanganate, chromic acid, and ferric chloride. It describes how primary, secondary, and tertiary alcohols react differently in oxidation reactions and confirmatory tests like the Lucas test. Phenol and substituted phenols are oxidized by potassium permanganate and bromine water. Their reactions with ferric chloride are also described. Guidelines for interpreting the results of the Lucas test are provided.

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    of 38

    ALCOHOLS, PHENOLS

    AND ETHERS
    Badilla, Tristan
    Diana, Emmanuel F.
    Fusin, Rosalinda
    Justol, Justine Sofia
    Ladera, Mike Daven
    Pangilinan, Ma. Diana
    Ragragio, Millaine Joy
    SCHEMATIC DIAGRAM
    OXIDATION OF REACTION PHENOLS
    ALCOHOLS
    LUCAS TEST
    1.Use the ff. test sample • Place 4pcs. pH paper on watch glass
    a.) Ethanol • Det. The pH of 0.1M sol’n of phenol,
    • Do the Test on the ff. sample b.) Isopropyl Alcohol p-nitrophenol, pictric acid, & p-methyl
    a.) Ethanol c.) Tert-butanol phenol by adding a drop of each to
    b.) Isopropyl Alcohol d.) Benzyl Alcohol separate pcs. pH paper.
    e.) Ethyl ether • Place 1ml phenol sol’n
    C.) Tert-butanol
    • To 1ml sample, + 0.5ml of dilute neutral • + bromine water drop by drop until
    d.) Benzyl Alcohol ppt. forms
    KMnO4, shake
    • To 1ml sample, + 6ml Lucas • Observe for decolorization of the violet color • Into 1ml phenol sol’n, + 1ml aqueous
    Reagent • Warm the mixture if decolorization takes neutral KMnO4
    • Shake place • Observe for decolorization of KMnO4
    • Note the time req’d for the for 2. Test compound to be used are: • To 1ml of 0.1M sol’n of phenol, ß-
    the formation of an emulsion/ a.) Ethanol naphthol, nitrophenol and
    separation layers. b.) Isopropyl Alcohol bromophenol in separate test tube, add
    c.) Tert-butanol a drop FeCl3 sol’n.
    d.) Benzyl Alcohol • Note the odor of resulting sol’ns.
    • To 1ml of acetone and 1 drp. Of test
    compound
    • +1d Chromic acid-sulfuric acid reagent &
    observe immediately.
    PERTINENT EQUATION
    &
    CONFIRMATORY
    (LUCAS TEST)
    1º Alcohol, 2º Alcohol, 3º Alcohol and Benzyl Alcohol
     𝑍𝑛𝐶𝐿 2
    •  
    + No reaction

     
     
       l +

     𝐼𝑠𝑜𝑝𝑟𝑜𝑝𝑦𝑙 𝐴𝑙𝑐𝑜h𝑜𝑙 2  ° 𝑎𝑙𝑘𝑦𝑙 𝑐h𝑙𝑜𝑟𝑖𝑑𝑒


     
       +  𝐻 2 𝑂 + 𝑍𝑛𝐶𝑙2

     𝑡 −𝑏𝑢𝑡𝑦𝑙 𝐴𝑙𝑐𝑜h𝑜𝑙 𝑡  − 𝑎𝑙𝑘𝑦𝑙 𝑐h𝑙𝑜𝑟𝑖𝑑𝑒


    𝑂𝐻
       𝐶𝑙
     
     + 𝐻𝐶𝑙  + 𝐻 2 𝑂

    𝐵𝑒𝑛𝑧𝑦𝑙
      𝐴𝑙𝑐𝑜h𝑜𝑙 𝐵𝑒𝑛𝑧𝑦𝑙
      𝐶h𝑙𝑜𝑟𝑖𝑑𝑒
    CONFIRMATORY

    1º Alcohol (Ethanol)-
    Colorless Solution

    2º Alcohol (Isopropyl
    Alcohol)- Turbid Solution

    3º Alcohol (T-Butyl
    Alcohol)- Turbid Solution

    Benzyl Alcohol- Turbid


    Solution
    OXIDATION OF ALCOHOLS
    ETHANOL
    IUPAC:
    Ethyl Alcohol
    Chemical Formula:
    (C2H5OH)
    EXPERIMENT NO.1:
    The Potassium Permanganate oxides primary alcohols in either basic or acidic solution. With primary alcohols the
    product normally is the carboxylic acid.

    • Oxidization of Ethanol with KMnO4


    H3C−CH2OH + H2O → H3C−CO2H + 4H+ + 4e−
    MnO4 −+ 4H+ + 3e− → MnO2(s) + 2H2O
    3H3C−CH2OH + 4MnO4- + 4H+→3H3C−CO2H + 4MnO2(s) + 5H2O

    • Confirmatory
    Discoloration of violet solution
    (Colorless Solution)
    EXPERIMENT NO.2:
    Primary alcohols are oxidized to carboxylic acids while the Cr+6 ion in the chromic acid is reduced to
    Cr+3.
    • Oxidation of Ethanol using Chromic Acid
    H2SO4 + CrO3 + H2O → H2CrO4
    acetone
    H2CrO4 + C2H5OH Cr3+ + CH₃COOH

    • CONFIRMATORY

    A blue-green color of solution in either layer.


    ISOPROPYL ALCOHOL
    IUPAC:
    2-Propanol
    Chemical Formula:
    (CH3CHOHCH3)
    EXPERIMENT NO.1:
    The Potassium Permanganate oxides secondary alcohols in either basic or acidic solution and yields
    ketone.
    • Oxidation of Isopropyl Alcohol using KMnO4

    3CH3CH(OH)CH3+ 2MnO4- + 2H+→ 3CH3COCH3+ 2MnO2(s) + 4H2O

    • CONFIRMATORY
    Discoloration of violet solution
    (Colorless solution)
    EXPERIMENT NO.2:
    Secondary alcohols are oxidized to ketones while the Cr +6 ion in the chromic acid is reduced to Cr+3.

    • Oxidation of Isopropyl Alcohol using Chromic Acid


    H2SO4 + CrO3 + H2O → H2CrO4
    acetone
    H2CrO4 + CH3CH(OH)CH3 Cr3+ + CH3COCH3

    • CONFIRMATORY
    Blue-green color of solution
    PERTINENT EQUATION
    &
    CONFIRMATORY
    (REACTION OF PHENOLS)
    PH PAPER CONFIRMATORY
    • 4-Nitrophenol can be used as a pH indicator. A solution of 4-nitrophenol
    appears colorless below pH 5.4 and yellow above pH 7.5.

    • The pH of a typical dilute solution of phenol in water is likely to be


    around 5 - 6 (depending on its concentration). That means that a very
    dilute solution isn't really acidic enough to turn litmus paper fully red.
    Litmus paper is blue at pH 8 and red at pH 5. Anything in between is
    going to show as some shade of "neutral".
    • Picric acid is a polynitrated aromatic acid. It dissolves in water to form a solution
    with low pH (pH 2.0).
    PHENOL WITH BROMINE WATER

    Odor: Musty or moldy


    smell
    PHENOL WITH NEUTRAL KMNO4

    KMnO4

    2,5-cyclohexadiene-1,4-ones
    (benzoquinones)

    Odor: Acrid, chlorine-like


    Phenol with FeCl3 REACTIONS WITH FERRIC CHLORIDE

    Ferric Phenoxide complex


    β-naphthol with FeCl3

    characteristic odor

    Green solution
    NITROPHENOL
    BROMOPHENOL

    + 3 HCl
    LUCAS REAGENT MECHANISM
    GUIDE Q3

    ZnCl2

    ROH + HCl—>RCl + H2O


    GUIDE Q2
    • In Lucas test, Zinc Chloride acts as catalyst. The classification of the alcohols is usually done
    based on the difference in reaction with concentrated hydrochloric acid. A simple reaction is
    given below:
    • ROH + HCl —>RCl + H2O
    • The points to note are:

    • The tertiary alcohol undergoes the most stable reaction and the primary alcohol undergoes the
    least stable reaction.
    • This test can be conducted only with those alcohols which are soluble in Lucas reagent and
    with lower molecular weight.
    • Alcohols generally with more than six carbon atoms cannot be tested, insolubility being the
    main reason here.
    The problem is that the alcohols themselves might be insoluble. Ethanol is
    soluble, yes, but as the alkyl chain length increases, the hydrophobic
    nature due to the chain starts dominating over whatever hydrophilicity
    the −OH−OH group had been providing for lower homologues.

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