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    Org Nitro Cpds Tutorial

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    Raffles Institution (Junior College) H2 Chemistry 2010/11 Tutorial 18 – Organic Nitrogen Compounds provides self-check and discussion questions about organic nitrogen compounds. The self-check questions ask students to order compounds by boiling point and explain properties of phenylalanine. The discussion questions ask students to order compounds by basic strength, write reactions for conversions between compounds, suggest tests to distinguish compounds, and identify structures from reactions.

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    Org Nitro Cpds Tutorial

    Uploaded by

    Dom
    121 views4 pages
    Raffles Institution (Junior College) H2 Chemistry 2010/11 Tutorial 18 – Organic Nitrogen Compounds provides self-check and discussion questions about organic nitrogen compounds. The self-check questions ask students to order compounds by boiling point and explain properties of phenylalanine. The discussion questions ask students to order compounds by basic strength, write reactions for conversions between compounds, suggest tests to distinguish compounds, and identify structures from reactions.

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    Organic Nitrogen Compounds Tutorial for A levels Chemistry.

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    Raffles Institution (Junior College) H2 Chemistry 2010/11 Tutorial 18 – Organic Nitrogen Compounds provides self-check and discussion questions about organic nitrogen compounds. The self-check questions ask students to order compounds by boiling point and explain properties of phenylalanine. The discussion questions ask students to order compounds by basic strength, write reactions for conversions between compounds, suggest tests to distinguish compounds, and identify structures from reactions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    121 views4 pages

    Org Nitro Cpds Tutorial

    Uploaded by

    Dom
    Raffles Institution (Junior College) H2 Chemistry 2010/11 Tutorial 18 – Organic Nitrogen Compounds provides self-check and discussion questions about organic nitrogen compounds. The self-check questions ask students to order compounds by boiling point and explain properties of phenylalanine. The discussion questions ask students to order compounds by basic strength, write reactions for conversions between compounds, suggest tests to distinguish compounds, and identify structures from reactions.

    Copyright:

    © All Rights Reserved
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    Raffles Institution (Junior College)

    H2 Chemistry 2010/11
    Tutorial 18 Organic Nitrogen Compounds

    Self-Check Questions
    1.

    Place the following compounds in the expected order of increasing boiling point.
    Give reasons for your answer.
    (a)
    (b)

    2.

    CH3CH2CH2NH2
    CH3CH2CH2CH3

    (c)
    (d)

    CH3CH2CH2OH
    CH3CH2NHCH3

    (e)

    (CH3)3N

    (a) Explain why phenylalanine although only slightly soluble in water, dissolves readily in
    aqueous acid and aqueous alkali.
    (b) To which electrode in an electrolytic cell would you expect the ions of phenylalanine to
    migrate in a solution of (i) pH = 1 and (ii) pH = 13?
    (c) In a solution of pH range 6-8, there is very little movement of phenylalanine towards the
    electrodes. What do you think is the nature of the species present in the solution at this
    pH?

    Discussion Questions
    1.

    Place the following compounds in the expected order of increasing basic strength.
    Give reasons for your answer.
    (a)

    O2N

    (b)

    2.

    NH 2

    CH2NH2

    (c)

    NH CH3

    (d)

    NHCOCH3

    (e)

    NH2

    Suggest the reagents and conditions required to carry out the following conversions.
    Write balanced equations for each step carried out.
    (a)

    CH3CH2Cl CH3CH2CH2NH2

    (b)

    CH2=CH2 CH3CONHCH2CH2NHCOCH3

    (c)

    CH3CONH2 CH3CONHCH2CH3

    (d)

    H3C COOH

    (CH3CH2)2NH

    (e)
    (e)

    CHO

    CH2CH2NH2

    -1-

    Br

    (f)
    Br

    (f)

    NH2
    Br

    (g)

    (g)CHCH
    3CH
    2CH2Br
    3CH2CH2Br

    NH2
    CH3CH2

    C COOH
    H

    3.

    Suggest simple chemical tests which can be carried out to distinguish between the
    members of the following groups of compounds. Write relevant equations for any reactions
    which occur.
    (a) phenylamine and (phenylmethyl)amine
    (b) CH3CH2CH2NH3+Cl and CH3CONH2
    (c)(d) H N
    2

    COCH3

    and

    CH3CONH
    HOCH2

    4.

    CO2CH2CH3

    H2N

    HO

    OH
    CH CH2 NH R

    Salbutamol (R = an alkyl group)

    benzocaine

    CH3

    D
    R

    C
    CO2CH2CH3

    S
    NH

    CH

    CH

    CH

    CH3
    CH3
    CO2H

    O
    penicillin (R = an aryl grouo)

    pethidine

    Write down the structural formula(e) of the organic product(s) obtained when
    (a) A, B, C and D are each treated with dilute hydrochloric acid at room temperature,
    (b) A, B and D are each heated with dilute hydrochloric acid,
    (c) A, B and C are each treated with ethanoyl chloride.

    5.

    A neutral compound A, C8H9NO, on refluxing with concentrated aqueous sodium hydroxide


    gives a solution of salt, B and a compound C (Mr = 93). With aqueous bromine, C forms a
    white precipitate D, C6H4Br3N.
    E is an isomer of A. On refluxing E with aqueous sodium hydroxide, ammonia gas is
    evolved and a salt F can be isolated from the reaction mixture. When F is refluxed with
    alkaline potassium manganate(VII) solution and the resulting mixture subsequently
    acidified, benzene-1,4-dicarboxylic acid is obtained.
    G is another isomer of A. On refluxing G with aqueous sodium hydroxide, an alkaline
    vapour, H, is obtained together with a salt solution I, C7H5O2Na. H reacts with ethanoyl
    chloride to form J, C3H7NO.
    Identify the compounds A to J with giving your reasons, and explaining all reactions using
    balanced equations.

    -2-

    Optional Question
    This question is about compound B, C9H9NO2, which forms zwitterions in aqueous solution
    and conducts electricity when a potential difference is applied across an aqueous solution
    of B at pH = 3.
    - On warming B with aqueous Na2CO3, a colourless gas which gave white precipitate with
    Ca(OH)2 is evolved.
    - With bromine water, B gives white precipitate, C, C9H7Br4NO2 and D, C9H6Br3NO3.
    - Treatment of 1 mole of B with hot acidified potassium permanganate gives a colourless
    solution and 2 moles of carbon dioxide gas. Controlled neutralization of the colourless
    solution gives a white precipitate, E, C7H7O2N.
    Compound E, dissolves in both NaOH(aq) and HCl (aq). Compound E can also be
    synthesized as indicated in the following sequence.
    CH3

    (i) Sn(s)/conc. HCl, reflux

    H+(aq)/MnO4F

    NO2

    heat

    E
    (ii) controlled addition of NaOH(aq)

    Deduce the structures of compounds B to F. Explain the chemistry of the reactions


    described, with the aid of equations where appropriate.

    -3-

    Self-Check Answers
    1.

    (a)
    (b)

    CH3CH2CH2NH2
    CH3CH2CH2CH3

    (c)
    (d)

    CH3CH2CH2OH
    CH3CH2NHCH3

    (e)

    (CH3)3N

    Expected order of increasing boiling point: (b) < (e) < (d) < (a) < (c).
    The 5 compounds have approximately the same Mr.
    (b) has the lowest b.p.. As the molecules are essentially non-polar, only id-id interactions exist between
    them.
    For (e), the molecules are polar and pd-pd interactions exist between them (no H-bonding because of
    absence of N-H group).
    For (d), the molecules can interact with each other through hydrogen bonding which is stronger than the
    van der Waals forces of attraction in (b) and (e).
    Hydrogen bonding between molecules of (a) is more extensive compared to that for (d) because the lone
    pair of electrons on the secondary amine is more sterically hindered for the formation of the H-bond.

    (c) has the highest b.p. because the molecules can interact with each other through OH ----O hydrogen
    bonding. This type of hydrogen bond is stronger than the NH ----N hydrogen bond since the OH bond is
    more polar (due to the more electronegative oxygen atom compared to the nitrogen atom) than the NH
    bond.
    2 (a)Phenylalanine is only slightly soluble in water because it contains the benzene ring which is
    hydrophobic.

    OH- (aq)

    CH2
    III

    H3N CH COO-

    H2N CH COO -

    H3N CH COOH
    H+ (aq)

    CH2
    I

    CH2
    II

    In aqueous acids and alkalis, phenylalanine exists as a cation (II) and an anion (III) respectively.
    In each case, a charged species is formed which can be more easily solvated by water molecules
    and thus solubility is enhanced.
    (b) (i) At pH=1, phenylalanine exists as cations and hence would migrate to the cathode (i.e. the
    negatively charged electrode).
    (ii) At pH=13, phenylalanine exists as anions and hence would migrate to the anode (i.e. the
    positively charged electrode).
    (c) At pH 6-8, phenylalanine exists predominantly as zwitterions. Such species possess no net
    charge (i.e. electrically neutral) and hence exhibits little movement towards the electrodes.

    -4-

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