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    Hydroxy Cpds Tut (Ans)

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    This document contains a chemistry tutorial on hydroxy and phenol compounds with 5 questions. It discusses the structures and reactions of alcohols with the molecular formula C4H10O, the reactions of a compound with various reagents, identifying structures based on reaction products, comparing acidities of compounds, and properties and reactions of isomeric alcohols. The tutorial provides detailed explanations and drawings of structures to answer multi-part questions involving identifying structures, explaining reactions, distinguishing between isomers, and more.

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    Hydroxy Cpds Tut (Ans)

    Uploaded by

    Dom
    89 views6 pages
    This document contains a chemistry tutorial on hydroxy and phenol compounds with 5 questions. It discusses the structures and reactions of alcohols with the molecular formula C4H10O, the reactions of a compound with various reagents, identifying structures based on reaction products, comparing acidities of compounds, and properties and reactions of isomeric alcohols. The tutorial provides detailed explanations and drawings of structures to answer multi-part questions involving identifying structures, explaining reactions, distinguishing between isomers, and more.

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    A level chemistry

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    This document contains a chemistry tutorial on hydroxy and phenol compounds with 5 questions. It discusses the structures and reactions of alcohols with the molecular formula C4H10O, the reactions of a compound with various reagents, identifying structures based on reaction products, comparing acidities of compounds, and properties and reactions of isomeric alcohols. The tutorial provides detailed explanations and drawings of structures to answer multi-part questions involving identifying structures, explaining reactions, distinguishing between isomers, and more.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    89 views6 pages

    Hydroxy Cpds Tut (Ans)

    Uploaded by

    Dom
    This document contains a chemistry tutorial on hydroxy and phenol compounds with 5 questions. It discusses the structures and reactions of alcohols with the molecular formula C4H10O, the reactions of a compound with various reagents, identifying structures based on reaction products, comparing acidities of compounds, and properties and reactions of isomeric alcohols. The tutorial provides detailed explanations and drawings of structures to answer multi-part questions involving identifying structures, explaining reactions, distinguishing between isomers, and more.

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    © All Rights Reserved
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    Download as pdf or txt
    of 6

    Raffles Institution (Junior College)

    H2 Chemistry 2010/11
    Tutorial 15 Hydroxy and Phenol
    Compounds
    Prepared by: Mr Chen Yongchang, Joseph

    Question 1
    (a)
    Draw the full structural formulae for all the alcohols with the molecular formula
    C4H10O and classify each as a primary, secondary or tertiary.
    (b)

    Compare and contrast the behaviour of these alcohols with oxidising agents such as
    acidified, aqueous potassium manganate(VII).

    (c)

    One of these alcohols is found to have the following properties.

    It exists as a pair of optical isomers.

    On warming with iodine and aq NaOH a pale yellow precipitate is obtained.

    On heating with an excess of concentrated sulphuric acid at 180oC a mixture


    of three alkenes is obtained.
    Identify the alcohol, explaining your reasoning. Also, give the full structural formulae
    of the three alkenes.

    Answer:
    (a)

    (b)

    All primary and secondary alcohols are oxidised by acidified, aqueous potassium
    manganate(VII). Tertiary alcohols are not oxidised.
    Observation: Purple KMnO4 turns colourless.
    Products: Primary alcohols to give carboxylic acids. Secondary alcohols to give
    ketones.

    (c)

    Butan-2-ol

    It possesses a chiral carbon. And it does not have a plane of symmetry. Thus,
    it exists as a pair of optical isomers.
    It possess a CH3CH(OH)- group. Hence the alcohol gives a positive iodoform
    test (yellow CHI3 ppt).
    CH3CH2CH(OH)CH3 + 4I2 + 6NaOH CHI3 + CH3CH2COO- + 5NaI + 5H2O

    Butan-2-ol undergoes dehydration to give three alkenes.

    Question 2
    How, and under what conditions would you expect a compound with the formula given below
    to react, if at all, with the following reagents? Draw the structural formula of the organic
    product(s) formed (if any) for reagents from (a) to (j).
    (a)
    (b)
    (c)
    (d)
    (e)
    (f)
    (g)
    (h)
    (i)
    (j)

    sodium
    sodium hydroxide
    sodium carbonate
    phosphorus(V) chloride
    hydrogen bromide
    ethanoic acid
    ethanoyl chloride
    aqueous bromine
    bromine in CCl4
    potassium manganate(VII)

    OH

    CH CHCH2OH

    Answer:
    (a)

    Phenolic and alcoholic OH react with sodium to form the respective phenoxide and
    alkoxide ion.
    Condition: Room temperature

    (b)

    Phenolic but not alcoholic OH reacts with sodium hydroxide.


    Condition: Room temperature

    (c)

    Both phenolic and alcoholic OH do not react with sodium carbonate which is a weak
    base.

    (d)

    Only the alcoholic OH gets substituted with Cl.


    Condition: Room temperature

    (e)

    Alcoholic OH gets substituted with Br and the electrophilic addition of HBr across
    the C=C bond.
    Condition: Room temperature

    (f)

    Alcoholic OH (but not phenolic OH) reacts with ethanoic acid to give an ester.
    Condition: Reflux, conc H2SO4 catalyst

    (g)

    Both Alcoholic and phenolic OH react with ethanoyl chloride to form esters.
    Condition: Room temperature

    (h)

    Both ring substitution (at 2-, 4- and 6-) and addition across the C=C bond occur.
    Condition: Room temperature

    (i)

    Both ring substitution and addition across the double bond occurs.
    Condition: Room temperature

    (j)

    Diol formation.
    Condition: Cold, dilute, alkaline KMnO4
    Oxidative cleavage of the double bond.
    Condition: Concentrated, acidified KMnO4, reflux

    Question 3
    Alcohol B, with the molecular formula of C5H12O, forms esters which are responsible for the
    flavours of various fruits. Reaction of B with acidified potassium dichromate(VI) produces a
    compound C, C5H10O2. Heating B over Al2O3 produces D, C5H10. Vigorous oxidation of D
    forms 2-methylpropanoic acid as one of the products.
    Suggest structures for B, C and D and explain the reactions involved.
    Answer:

    Compound

    Structural Formula

    H3C CH

    CH2

    CH2OH

    CH2

    COOH

    CH

    CH2

    CH3

    H3C CH
    CH3

    H3C CH
    CH3

    B being an alcohol undergoes dehydration when heated with Al2O3 to give an alkene D.
    Oxidation of D forms 2-methlypropanoic acid, which suggest that D is a terminal alkene.
    Therefore, the suggestion for D is a 3-methylbut-1-ene.

    Product D
    H3C CH CH

    [O]

    CH2

    2-methlypropanoic acid
    H3C CH

    CH3

    CH2

    COOH

    CO2

    H2O

    CH3

    Oxidation of B to C gives an additional oxygen in product C, which suggests C is a


    carboxylic acid. Therefore, B must be a primary alcohol in order to oxidize into a carboxylic
    acid.

    Product B
    H3C CH
    CH3

    CH2

    [O]

    CH2OH

    Product C
    H3C CH CH2

    COOH

    CH3

    Question 4
    Arrange the following in order of increasing acidity:
    phenol, 2-nitrophenol, ethanol, methylpropan-2-ol, water, methanol, 2-methylphenol.
    Explain your answer.
    Answer:
    methylpropan-2-ol < ethanol < methanol < water < 2-methylphenol < phenol < 2-nitrophenol

    In general, acidity: alcohol < water < phenol.


    The relative acid strength depends on the relative stability of the respective conjugate bases,
    namely the phenoxide, the hydroxide and the ethoxide ions. The more stable the conjugate
    base, the more acidic the compound.
    Alcohols

    contain alkyl groups which are electron donating, intensify electron density on O
    atom

    destabilise the alkoxide ions (compared to hydroxide ions)

    acidity decreases as number of alkyl group increases.


    Phenols

    phenoxide ions are stabilised by delocalisation of the negative charge on the oxygen
    into the ring.
    Phenol containing an electron-releasing substituent (e.g. methyl group)

    less acidic than an unsubstituted phenol

    delocalisation of negative charge into the ring is hindered


    Phenol containing an electron-withdrawing substituent (e.g. nitro group)

    more acidic than an unsubstituted phenol

    delocalisation of negative charge into the ring is enhanced.


    Question 5
    CH3CH(OH)CH2CH3
    A

    (CH3)3COH
    B

    Alcohols A and B are isomers.


    (a) Draw the structural formula of one other alcohol isomeric with A and
    B.
    (b) What reagent would you use to dehydrate A and B to alkenes? Draw
    the structural formulae of the three alkenes that are obtained by
    dehydrating A.
    (c) Describe a reaction (reagent and observation) by which A could be
    distinguished from B.
    (d) Name the class of compound formed when A reacts with ethanoyl
    chloride, and draw its structural formula.
    (e) Draw diagrams to illustrate how A gives rise to optical isomerism.

    [1]

    [3]

    [2]
    [2]
    [2]

    N92/I/9
    (a)

    CH3(CH2)3OH

    (b)

    Conc. H2SO4 and 170oC

    (c)

    Tri-iodomethane test. When iodine and sodium hydroxide is warmed with A,


    yellow crystals of tri-iodomethane are formed. There is no precipitate
    observed with B.

    (d)

    Ester Group
    (e)

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