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    Suggested Solutions To Discussion Questions Carboxylic

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    Dom
    The document summarizes the following: 1. It provides explanations for the relative acid strengths of various carboxylic acids and phenols based on stabilization of the conjugate base by resonance or inductive effects. 2. It outlines tests to distinguish between three unknown organic compounds (E, F, and G) based on their reactions with sodium hydroxide, sodium carbonate, and properties. 3. It describes a series of organic synthesis reactions involving oxidation, halogenation, substitution, hydrolysis, and condensation to transform one compound to another.

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    Suggested Solutions To Discussion Questions Carboxylic

    Uploaded by

    Dom
    449 views5 pages
    The document summarizes the following: 1. It provides explanations for the relative acid strengths of various carboxylic acids and phenols based on stabilization of the conjugate base by resonance or inductive effects. 2. It outlines tests to distinguish between three unknown organic compounds (E, F, and G) based on their reactions with sodium hydroxide, sodium carbonate, and properties. 3. It describes a series of organic synthesis reactions involving oxidation, halogenation, substitution, hydrolysis, and condensation to transform one compound to another.

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    A level chemistry

    Original Title

    Suggested Solutions to Discussion Questions Carboxylic

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    The document summarizes the following: 1. It provides explanations for the relative acid strengths of various carboxylic acids and phenols based on stabilization of the conjugate base by resonance or inductive effects. 2. It outlines tests to distinguish between three unknown organic compounds (E, F, and G) based on their reactions with sodium hydroxide, sodium carbonate, and properties. 3. It describes a series of organic synthesis reactions involving oxidation, halogenation, substitution, hydrolysis, and condensation to transform one compound to another.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    449 views5 pages

    Suggested Solutions To Discussion Questions Carboxylic

    Uploaded by

    Dom
    The document summarizes the following: 1. It provides explanations for the relative acid strengths of various carboxylic acids and phenols based on stabilization of the conjugate base by resonance or inductive effects. 2. It outlines tests to distinguish between three unknown organic compounds (E, F, and G) based on their reactions with sodium hydroxide, sodium carbonate, and properties. 3. It describes a series of organic synthesis reactions involving oxidation, halogenation, substitution, hydrolysis, and condensation to transform one compound to another.

    Copyright:

    © All Rights Reserved
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    Download as pdf or txt
    of 5

    Suggested Solutions to Discussion Questions (Tutorial 17)

    1. (a)
    Ethyl ethanoate Ethanol
    <
    Phenol
    <
    <
    Consider a weak acid, HA
    HA
    H+
    +
    A
    More stable A, greater dissociation, stronger acid.
    No acidic proton electron donating benzene
    ring
    present.
    ethyl group
    present
    allows
    intensifies
    delocalisation of of
    cannot act as
    negative charge
    negative charge on
    an acid!
    and destabilizes
    Oalkoxide anion
    O of
    into
    benzene
    ring
    stabilizing
    the
    phenoxide ion

    ethanoic acid <

    negative charge is
    dispersed over 2
    electronegative
    oxygen atoms in 2
    equivalent
    resonance
    structures causing
    the anion to be
    greatly stabilised

    benzoic acid [1]

    Presence
    of
    benzene
    enables
    delocalisation of
    negative charge in
    the anion into the
    benzene
    ring,
    stabilising the anion

    (b) CH3CH2CH2CH2COOH < CH3COOH < HOCH2COOH < CCl3COOH


    HA
    H+
    +
    A
    More stable A, greater dissociation, stronger acid.
    Compare stability of A, taking CH3COO as reference:
    alkyl groups are elctron donating by inductive effect. It intensifies the negative
    charge & destabilises the anion. CH3CH2CH2CH2COO is only slightly less stable
    than CH3COO due to longer alkyl chain (effect of alkyl chain length is minimal)
    OH is electron withdrawing by inductive effect. It helps to disperse the negative
    charge & stabilises the anion. HOCH2COOH is more acidic than CH3COOH.
    the presence of 3 Cl atoms (electron withdrawing by inductive effect) disperses the
    negative charge extensively. CCl3COO is greatly stabilised & CCl3COOH is the
    strongest acid among the 4.
    2.

    All three compounds react with Na(s) to give effervescence of H2(g) and the
    corresponding Na+ salts which are soluble in water.
    E

    CH2OH

    H3C

    OH

    Na (s)

    COOH

    Na(s)

    CH2O Na + 1/2 H2

    H3C

    O Na + 1/2 H2

    Na (s)

    COO Na + 1/2 H2

    G
    Both E and F have no reaction with aqueous Na2CO3. G reacts with aq. Na2CO3 to
    give effervescence of CO2(g) and Na+ salt which is soluble in water.

    COOH

    + Na2CO3 (aq)

    COO Na + CO2

    G
    1

    E has no reaction with aqueous NaOH. Both F and G react with NaOH to give the
    corresponding Na+ salts which are soluble in water.

    H3C

    OH

    + NaOH (aq)

    H3C

    O Na + H2O

    + NaOH (aq)

    COOH

    COO Na + H2O

    G
    Add aqueous Na2CO3 to the sample. If effervescence of CO2 is detected, then the
    sample is G. If not, then the sample is either E or F, which can be differentiated by
    adding aqueous NaOH. Only F is soluble in aqueous NaOH.
    3. C6H5COOH
    and
    C6H5OH
    [acid strength]
    Test:
    Add Na2CO3 (aq)
    [or NaHCO3 (aq)]
    Observations: Effervescence observed.
    No effervescence observed
    Colourless gas (CO2) evolved
    formed white ppt with aq. Ca(OH)2
    Equation:
    2 CH3COOH + Na2CO3 2 CH3COONa+ + CO2 + H2O
    (b) HOCH2CH2COCl
    and
    ClCH2CH2COOH [acyl chloride vs acid]
    Test:
    Add AgNO3(aq)
    Observations: White fumes
    No white fumes
    White ppt (AgCl)
    No ppt observed
    Equation:
    HOCH2CH2COCl + H2O HOCH2CH2COOH + HCl
    Cl(aq) + Ag+(aq) AgCl (s)
    (c)C6H5COCl and C6H5COBr and C6H5CH2Cl [acyl chloride vs acyl bromide vs alkyl halide]
    Test:
    Add AgNO3(aq)
    Observations: White fumes
    White fumes
    White fumes
    White ppt (AgCl) Off-white ppt (AgBr)
    White ppt (AgCl) only when
    heated
    Equation:
    C6H5COX + H2O C6H5COOH + HX
    C6H5CH2Cl + H2O
    C6H5CH2OH + HCl
    X(aq) + Ag+(aq) AgX (s)
    X= Cl, Br
    Cl(aq) + Ag+(aq) AgCl (s)
    (d) CH3COOCH2CH2CH3
    and
    CH3COOCH(CH3)2
    Test:
    1) Heat with NaOH (aq)
    2) Add aq. I2
    Observations: No yellow ppt formed
    yellow ppt formed

    Equation:
    CH3COOCH2CH2CH3 +OH CH3COO + HOCH2CH2CH3
    CH3COOCH(CH3)2 +OH CH3COO + HOCH(CH3)2
    HOCH(CH3)2 + 4I2 + 6OH CH3COO + CHI3 + 5I + 5H2O

    4.

    (a)

    2
    4
    CH3COOH + H2O
    CH3CH2OH + [O]
    heat

    dilH SO , aq.KMnO

    2
    CH3COOH
    CH3COCl + SO2 + HCl
    room temperature

    SOCl

    O=

    (b)

    (c)

    room temperature
    CH3CH2OH + CH3CH2COCl
    CH3C-O-CH2CH3
    (from a)

    CH3CH2OH + [O]

    K2Cr2O7(aq), dil H2SO4, heat


    with immediate distillation

    CH3CHO + H2O

    O
    CH3

    C H

    OH

    KCN

    HCN

    CH3

    C CN
    H

    OH
    CH3

    C CN

    OH

    dil HCl
    + 2H2O + H+

    H
    (d)
    CH3CH2CH2OH + 2 [O]

    CH3

    C COOH

    heat

    + NH4+

    KMnO4 (aq), dil H2SO4,


    heat

    CH3CH2COOH + H2O

    room temperature

    CH3CH2COOH + SOCl2

    CH3CH2COCl + SO2 + HCl


    O

    +CH3CH2COCl + Na O

    5.

    C O

    + NaCl

    COCl

    COOH

    room temperature
    SOCl2

    COCl

    +
    6.

    CH3CH2

    NH2CH2COOH

    HCl

    room temperature
    CONHCH 2COOH

    SO2

    HCl

    F undergoes neutralization with NaOH(aq)

    F contains an acidic fn gp
    F is either a phenol or a carboxylic acid
    F undergoes condensation reaction with 2,4-DNPH but does not undergo oxidation with
    Fehlings solution
    F is a carbonyl compound that is not an aliphatic aldehyde
    F is either an aromatic aldehyde or a ketone
    F undergoes electrophilic substitution with Br2 water to give G.

    F contains a strongly activated benzene ring


    F is a phenol
    Since G has 2 H atoms substituted with 2Br atoms
    G is a 2- or 4-substituted phenol
    F gives a positive iodoform test to yield H
    F is a methyl ketone
    H is a carboxylic acid with 1 C less
    H undergoes neutralization with both NaOH(aq) and Na2CO3(aq).
    H is a carboxylic acid (confirmed)
    H is obtained by alkaline hydrolysis of J followed by acidification.
    H is 1,2-disubstituted.
    OH

    O
    C

    OH

    H is
    OH

    OH

    Br

    O
    C

    OH
    CH3

    O
    C

    CH3

    OH

    Br

    [1] per correct structure

    Equations:
    [F + NaOH]
    OH

    O-Na+ O

    O
    C

    CH3

    + NaOH

    CH3

    + H 2O

    [F + 2,4-DNPH]
    OH

    OH

    O2N

    CH3

    CH3
    C

    H2NNH

    NO2

    O2N

    NNH

    NO2 + H2O

    [F + Br2(aq)]
    OH

    O
    C

    OH
    CH3

    Br

    O
    C

    + 2Br2

    CH3

    + 2HBr

    Br

    [F + aq. alkaline I2]

    OH

    O-

    O
    C

    O
    C

    CH3 + 3I2 + 5OH-

    O-

    + CHI3 + 3I- + 4H2O

    [acidification after iodoform test]


    [acidification after J + NaOH]
    O-

    OH

    O
    C

    O-

    O
    C

    + 2H

    OH

    [J + NaOH]
    OH

    O-

    O
    C

    OCH3

    O
    C

    + 2OH-

    O-

    + H2O

    + CH3OH

    [J + Na2CO3]
    OH
    2

    OH

    O
    C

    OH

    + Na2CO3

    O
    C

    O-Na+

    + CO2 + H2O

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