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    Alcohols, Phenols and Ethers

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    Anonymous GO6JVW9Wud
    This document summarizes the results of experiments performed to identify various alcohols, phenols, and ethers using common chemical tests like the Lucas test and reaction with potassium permanganate. It provides balanced equations for the reactions and explains why tertiary alcohols and ethers do not undergo oxidation with potassium permanganate and why the Lucas test is only applicable to alcohols with 5 or fewer carbons. It also correlates the structures of different phenolic compounds with their measured pH values.

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    Alcohols, Phenols and Ethers

    Uploaded by

    Anonymous GO6JVW9Wud
    3K views4 pages
    This document summarizes the results of experiments performed to identify various alcohols, phenols, and ethers using common chemical tests like the Lucas test and reaction with potassium permanganate. It provides balanced equations for the reactions and explains why tertiary alcohols and ethers do not undergo oxidation with potassium permanganate and why the Lucas test is only applicable to alcohols with 5 or fewer carbons. It also correlates the structures of different phenolic compounds with their measured pH values.

    Original Description:

    Chem 31.1 ATQ- Experiment 7

    Original Title

    ALCOHOLS, PHENOLS AND ETHERS

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    This document summarizes the results of experiments performed to identify various alcohols, phenols, and ethers using common chemical tests like the Lucas test and reaction with potassium permanganate. It provides balanced equations for the reactions and explains why tertiary alcohols and ethers do not undergo oxidation with potassium permanganate and why the Lucas test is only applicable to alcohols with 5 or fewer carbons. It also correlates the structures of different phenolic compounds with their measured pH values.

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    © All Rights Reserved
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    Download as docx, pdf, or txt
    3K views4 pages

    Alcohols, Phenols and Ethers

    Uploaded by

    Anonymous GO6JVW9Wud
    This document summarizes the results of experiments performed to identify various alcohols, phenols, and ethers using common chemical tests like the Lucas test and reaction with potassium permanganate. It provides balanced equations for the reactions and explains why tertiary alcohols and ethers do not undergo oxidation with potassium permanganate and why the Lucas test is only applicable to alcohols with 5 or fewer carbons. It also correlates the structures of different phenolic compounds with their measured pH values.

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    © All Rights Reserved
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    of 4

    ALCOHOLS, PHENOLS AND ETHERS

    J.V. DE GUZMAN
    DEPARTMENT OF CHEMICAL ENGINEERING, COLLEGE OF ENGINEERING
    UNIVERSITY OF THE PHILIPPINES, DILIMAN QUEZON CITY, PHILIPPINES
    DATE PERFORMED: FEBRUARY 27, 2015
    INSTRUCTORS NAME: ALLAN KENNETH REGUNTON

    ANSWERS TO QUESTIONS
    1. Give the balance equations for all the reactions.
    a. Ethyl alcohol + Lucas Reagent
    ZnCl2

    + HCl
    No reaction (clear, colorless solution)
    b. Isopropyl Alcohol + Lucas Reagent
    ZnCl2

    + HCl

    + H2O
    (slow)

    Insolule-cloudiness

    c. Benzyl alcohol + Lucas Reagent


    ZnCl

    + HCl

    +HO

    Insolule-cloudiness
    2

    d. Tert-butyl alcohol + Lucas Reagent


    ZnCl
    2

    + HCl
    e. Ethyl alcohol + KMnO4

    Insolule-cloudiness

    + MnO4Balanced:
    CH3-CH2-OH +
    COH=O +
    H2O
    f. Isopropyl alcohol + KMnO4

    + MnO4-

    + H2O

    + MnO4MnO4-(aq)

    (fast)

    MnO2(s) +

    + MnO2(s) + 2H2O

    + MnO2(s)
    CH3-

    g. Benzyl alcohol + KMnO4

    + MnO4h. Tert-butyl alcohol + KMnO4

    + MnO4i. Diethyl ether + KMnO4

    + MnO2(s) + H2O

    No Reaction

    + MnO4j. Phenol + Bromine water

    No Reaction

    + 3Br2
    k. Phenol + KMnO4

    + 3HBr

    + MnO4l. Phenol + FeCl3


    36
    + FeCl3
    + 3Clm. p-nitrophenol + FeCl3

    3
    + FeCl3
    HCl
    n. p-bromophenol + FeCl3

    3
    + 3HCl

    + FeCl3

    Fe

    + 6H+

    Fe

    Fe

    o. -naphthol + FeCl3

    + FeCl3
    3

    Fe

    + 3HCl

    2. Why is Lucas Test applicable only to alcohols containing 5 or


    less carbons?
    Lucas test makes use of the solubility of the reagent for the reaction to
    happen. As such, this method applies only for alcohols that are soluble
    in the reagent in order for the chlorination reaction of the alcohol to
    occur. Lucas reagent is a solution of ZnCl 2 in HCl, as such; this polar
    solution dissolves only highly polar alcohols or those that have less
    number of non-polar groups. More than 5 carbons, the alcohol becomes
    more nonpolar, therefore, Lucas test is applicable only to alcohols with
    less than 5 or less carbons.
    3. Why tertiary alcohols and ethers cannot undergo oxidation
    upon reaction with potassium permanganate?
    Oxidation of the alcohol depends on its relative stability. As the number
    of alkyl substituent of the carbon of which the hydroxide is bonded
    increases, the greater is the stability of the alcohol. Therefore, it can be
    arranged that tertiary alcohol>secondary alcohol>primary alcohol in
    terms of stability. Permanganate can oxidize primary alcohols into
    aldehyde then into carboxylic acids and secondary alcohols into
    ketones only. However, potassium permanganate cannot remove an
    electron from a tertiary alcohol to oxidize it because of its great
    stability. The same also applies for diethyl ether. The symmetric
    structure of diethyl ether gives stability to the molecule as such
    permanganate cannot withdraw an electron form it.
    4. Correlate the structure of the phenolic compounds with the measured
    pH values.
    Given are the structure and corresponding pH values of phenolic
    compounds:

    Picric acid (pH=3)

    p-nitrophenol

    Phenol (pH=5)

    The relative acidity of phenolic compounds is dependent on electron


    withdrawing groups attach to the ring. As the electron withdrawing group
    increases, the benzene ring becomes more positively charged thereby
    making the compound more acidic. In phenol, there is only one electron (OH) withdrawing group and two for p-nitrophenol (-OH and NO2) making
    nitrophenol more acidic than phenol. Picric acid has four electron
    withdrawing groups (-OH and 3(-NO2)) making it the strongest organic acid.
    This idea correlates with the obtained pH values of the phenolic compounds:
    picric acid > p-nitrophenol > phenol in terms of relative acidity.
    REFERENCES:
    [1]Pahlavan, L. Properties of Alcohol: structure, reactions and identification
    of alcohols. Southwest College Houston Community College. [Online].
    2014. Retrieved from: http://swc2.hccs.edu/pahlavan/2425L4.pdf
    (accessed March 3, 2015).
    [2]Pavia, D. L., Lampman, G. M., Kriz, G.S., Engel, R. Introduction to Organic
    Laboratory Techniques: A Microscale Approach. Part 3: Identification of
    Organic Substances-Experiment 53H: Alcohols. Saunders College
    Publishing: Orlando, 1995. pg 513.
    [3]Xiamen University. Oxidation of Alcohols. [Online]. 2002. Retrieved from:
    http://chem.xmu.edu.cn/teach/yjhx/chem/02en/chpt12_2.pdf (accessed
    March 3, 2015).

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