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    Raffles Institution (Junior College) H2 Chemistry 2008/9 Tutorial - Hydroxy and Phenol Compounds

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    This document is a chemistry tutorial on hydroxy and phenol compounds that contains 5 questions: 1) Identifying alcohols with the molecular formula C4H10O and their behavior with oxidizing agents. One alcohol is identified based on its properties. 2) Predicting the reactions of an alcohol with various reagents and drawing the organic products. 3) Suggesting structures for alcohols B, C, and D based on their reactions. B flavors fruits and forms esters. 4) Ranking compounds in order of increasing acidity and explaining the order. 5) Questions about isomeric alcohols A and B, including drawing another isomer, dehydration

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    Raffles Institution (Junior College) H2 Chemistry 2008/9 Tutorial - Hydroxy and Phenol Compounds

    Uploaded by

    Dom
    138 views2 pages
    This document is a chemistry tutorial on hydroxy and phenol compounds that contains 5 questions: 1) Identifying alcohols with the molecular formula C4H10O and their behavior with oxidizing agents. One alcohol is identified based on its properties. 2) Predicting the reactions of an alcohol with various reagents and drawing the organic products. 3) Suggesting structures for alcohols B, C, and D based on their reactions. B flavors fruits and forms esters. 4) Ranking compounds in order of increasing acidity and explaining the order. 5) Questions about isomeric alcohols A and B, including drawing another isomer, dehydration

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    A level Chemistry

    Original Title

    0809 Hydroxy Cpds Tut

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    This document is a chemistry tutorial on hydroxy and phenol compounds that contains 5 questions: 1) Identifying alcohols with the molecular formula C4H10O and their behavior with oxidizing agents. One alcohol is identified based on its properties. 2) Predicting the reactions of an alcohol with various reagents and drawing the organic products. 3) Suggesting structures for alcohols B, C, and D based on their reactions. B flavors fruits and forms esters. 4) Ranking compounds in order of increasing acidity and explaining the order. 5) Questions about isomeric alcohols A and B, including drawing another isomer, dehydration

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    138 views2 pages

    Raffles Institution (Junior College) H2 Chemistry 2008/9 Tutorial - Hydroxy and Phenol Compounds

    Uploaded by

    Dom
    This document is a chemistry tutorial on hydroxy and phenol compounds that contains 5 questions: 1) Identifying alcohols with the molecular formula C4H10O and their behavior with oxidizing agents. One alcohol is identified based on its properties. 2) Predicting the reactions of an alcohol with various reagents and drawing the organic products. 3) Suggesting structures for alcohols B, C, and D based on their reactions. B flavors fruits and forms esters. 4) Ranking compounds in order of increasing acidity and explaining the order. 5) Questions about isomeric alcohols A and B, including drawing another isomer, dehydration

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    Raffles Institution (Junior College)

    H2 Chemistry 2008/9
    Tutorial 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 dichromate (VI).

    (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.

    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

    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.
    J94/I/10

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

    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.
    [1]
    (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.
    [3]
    (c)
    Describe a reaction (reagent and observation) by which A could be distinguished
    from B.
    [2]
    (d)
    Name the class of compound formed when A reacts with ethanoyl chloride, and draw
    its structural formula.
    [2]
    (e)
    Draw diagrams to illustrate how A gives rise to optical isomerism.
    [2]
    N92/I/9

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