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  • Which of the following is NOT a pair of isomers?
    butan-2-one and butan-1-ol
    ethyl benzene and 1,2-dimethylbenzene
    pentan-2-one and pentanal
    urea and ammonium cyanate
  • If n=2, what is l and ml respectively?
    l = 0, 1; ml= -1, 0, +1
  • Examine the diagrams below carefully. Which of the burets shown below is/are ready for use?
    1
    3
    4 only
    2
  • What is the major functional group shown here?
    Primary amine
  • Are these: conformational isomers, stereoisomers, constitutional isomers OR identical
    identical
  • What are the reagents?
    1. NaNH2, NH3 2. CH3CH2I
  • If 3-chloro-3-methylpentane is heated in alcoholic potassium hydroxide, how many structural (constitutional) alkene isomers could be produced?
    2
    4
    3
    1
  • Calculate the ΔG°, in kJ, for the spontaneous reaction, if the E = 0.79V
    -1.5E2 kJ
  • This is an example of:
    E1 process
    SN1 process
    SN2 process
    E2 process
  • What is the bond order of O2–
    1.5
  • Consider the acidity constants below to answer the following question. Which acid will be almost completely deprotonated by NaOH?
    phenol
  • The electrophile in aromatic nitration.
    +NO
    +NO2
    F-TEDA-BF4
    benzyne
  • Which of the following is the correct order of boiling points for KNO3, CH3OH, C2H6, Ne?
    C2H6 < Ne < CH3OH < KNO3
    Ne < C2H6 < CH3OH < KNO3
    Ne < C2H6 < KNO3 < CH3OH
    Ne < CH3OH < C2H6 < KNO3
  • Which of the following is a meta- director?
    —OH
    —CH2CH2CH3
    —Br
    —COCH3
  • Which of the following compounds would show the longest wavelength λmax in its UV spectrum?
    a
    d
    b
    c
  • which of the following would have the formula C5H10O
    pent-3-en-1-al
    methoxybutane
    pentanol
    pentanone
  • What reagent(s) can be used for this reaction?
    BH3, THF H2O2, NaOH, H2O OR just water in acid
  • For nitrous acid, HNO2, Ka = 4.0 × 10–4. Calculate the pH of 0.54 M HNO2.
    1.83
  • Which reaction would be faster and WHY
    −SH is a better nucleophile than −OH because nucleophilicity usually increases in going down a column of the periodic table and sulfur is below oxygen in group
  • Cubic closest packing is another name for _____________.
    body-centered cubic packing
    simple cubic packing
    hexagonal closest packing
    face-centered cubic packing
  • What VSEPR molecular shape do you expect for IF4 +?
    seesaw
  • What would be the best reagent for this reaction
    LiAlH4 in ether, then H3O+
    NaH, then CH3I
    Hg(O2CCF3)2, CH3OH
    PCC, CH2Cl2
  • How many unpaired electrons in the F2 2+ ion are based on molecular orbital theory? The order of the molecular orbitals are (σ2s)(σ*2s)(σ2p)(π2p)(π*2p)(σ*2p).
    2
  • Are these: conformational isomers, stereoisomers, constitutional isomers OR identical
    stereoisomers
  • This is the amino acid valine. Is it chiral? Explain
    yes, the carbon where NH2 is.
  • What is the value of ε°cell?
    -0.676
    2.836
    0.676
    0.176
  • Name this
    N-aminopentane
    N-ethylpropanamine
    butanamide
    ethyl amino butane
  • What's the best reagent?
    1) CH3MgBr, ether 2) acid treatment
    CrO3, acetone, H2O
    1) LiAlH4, ether 2) acid treatment
    1) NaBH4, ethanol 2) acid treatment
  • What would be the best reagent for this reaction
    PCC, CH2Cl2
    LiAlH4 in ether, then H3O+
    warm H2SO4/H2O
    m-ClC6H4CO3H
  • Which of the following is a good approximation of the equilibrium temperature for the reaction at 200 000 atm if enthalpy and entropy are assumed to be temperature independent?
    T = 100 K
    T = 3000 K
    T = 4000 K
    T = 1000 K
  • Intermediate in the elimination-addition mechanism of nucleophilic aromatic substitution.
    benzyne
    electron-donating
    Meisenheimer complex
    electron-withrawing
  • Which is the most basic?
    A
    D
    B
    C
  • Which is the most reactive toward electrophilic aromatic substitution
    toluene (the one in the middle)
  • What are the reagents?
    1. BH3, (THF) 2. H2O2, (NaOH, H2O)
  • What's the best reagent?
    Dess-Martin periodinane
    1) NaBH4, ethanol 2) acid treatment
    1) CH3MgBr, ether 2) acid treatment
    1) LiAlH4, ether 2) acid treatment
  • What would be the best reagent for this reaction
    LiAlH4 in ether, then H3O+
    PCC, CH2Cl2
    warm H2SO4/H2O
    CH3MgBr in ether, then H3O+
  • If four orbitals on one atom overlap four orbitals on a second atom, how many molecular orbitals will form?
    8
  • Which is most similar for the elements in a group in the periodic table?
    ground state electron configuration
    boiling point
    first ionization energy
    physical state
  • What do you see in a mass spec if there is an alcohol
    M-18 and also alpha cleavage
  • WhWhich of the peak in the IR spectrum shown is due to the C—O stretch in an alcohol?
    3
  • The oxidation number of Fe in K3Fe(CN)6 is:
    +3
  • How many bridgehead carbons are there in camphor?
    2
  • What would be the best reagent for this reaction
    warm H2SO4/H2O
    CH3MgBr in ether, then H3O+
    LiAlH4 in ether, then H3O+
    PCC, CH2Cl2
  • What type of reaction is this?
    addition/hydration
  • How many different tripeptides can be formed from the amino acids glycine, alanine and valine if each is used only once in each tripeptide?
    3
    5
    4
    6
  • When ignited, a uranium compound burns with a green flame. The wavelength of the light given off by this flame is greater than that of
    radio waves
    IR light
    red light
    UV light
  • Which of these compounds would you expect to be water soluble?
    propanoic acid and naproxen
  • Is furan aromatic? Why or why not?
    Furan is a planar and conjugated. Furan has 6 π electrons. The additional electron pair of the oxygen atom is not part of aromatic π system. It is aromatic
  • Which of the following compounds will react as a diene in a Diels-Alder reaction?
    d
    a
    c
    b
  • The stereochemical configuration at C3 (one answer to be given only)
    R
  • Name the 2 products
    iodoethane and butan-2-ol
  • What is the product of oxidation of propan-2-ol
    propanoic acid
    propan-2-one
    propene
    propanal
  • What's the best reagent?
    Dess-Martin periodinane, CH2Cl2
    1) LiAlH4, ether 2) acid treatment
    1) CH3MgBr, ether 2) acid treatment
    1) NaBH4, ethanol 2) acid treatment
  • Which of the following could be used to convert butan-1-ol to butan-1-amine?
    Treat with dilute H2SO4 then with concentrated NH3
    Treat with SOCl2 and then with concentrated NH3
    Treat with concentrated H2SO4 then with concentrated NH3
    Treat with concentrated NH3
  • What would be the best reagent for this reaction
    LiAlH4 in ether, then H3O+
    warm H2SO4/H2O
    CH3MgBr in ether, then H3O+
    PCC, CH2Cl2
  • What reagent can be used
    CH2I2, Zn(Cu)
  • How many d electrons are present on the metal ion in the complex ion FeCl64–?
    6
  • Name this
    2-propoxybutane
  • Based on the following table, in which compound is the energy difference between the HOMO and LUMO the largest?
    X
    Z
    W
    Y
  • What is the molecular formula of this natural product?
    C13H10
  • Which of the following is an ortho- and para- director and a deactivator?
    —Cl
    —OH
    —COCH3
    —CH2CH2CH3
  • What is E o for the reaction 2 H2(g) + O2(g) → 2 H2O(l)?
    4.06 V
    2.06 V
    0.43 V
    1.23V
  • compound with specific rotation, [α]D = +35.4° reacts to form a single product. The product of the reaction has no optical activity. This could mean the product:
    all are possible
    does not have chiral centers
    is a racemate.
    is a meso compound
  • The stereochemical configuration of the C4-C5 alkene is
    Z
  • What is the electrophile in this reaction
    B
    doesn't apply
    C
    A
  • This is an example of a(n) ____________ reaction.
    Diels-Alder
  • What is a major peak of an alcohol in IR?
    broad peak at around 3400
  • The hybridization of the nitrogen atom
    sp3
  • Which of the following will undergo rearrangement upon heating?
    2-butenyl phenyl ether
    1-propenyl 2-propenyl ether
    All will undergo rearrangement.
    2-pentenyl phenyl ether
  • Based on the pKas for their corresponding ammonium ions, which arylamine above is the strongest base?
    they are all the same
    p-aminoaniline
    p-cyanoaniline
    aniline
  • What is the electron configuration of the Mn(II) ion?
    [Ar] 3d5
  • Which of the following is NOT a strong base? 1. Be(OH)2 c. NaOH 2. Li2O d. CaO
    Be(OH)2
  • Identify 1 and 2 (if you only get one correct, you will only receive 5 marks and include catalysts)
    1) HNO3, H2SO4 2) Br2, FeBr3
  • Which alkene would you use to prepare (1-bromoethyl)cyclohexane
    ethenylcyclohexane
  • Which signal in the following proton NMR is due to an alcohol proton?
    3
    4
    2
    1
  • What are the reagents?
    1. BH3, (THF) 2. H2O2, (NaOH, H2O)
  • The amount of energy in electromagnetic radiation is related to the frequency and wavelength of the radiation. High energy radiation like gamma rays is of:
    low frequency and long wavelength
    high frequency and short wavelength
    high frequency and long wavelength
    low frequency and short wavelength
  • Name the product
    cyclopentene
  • Name the product
    5-bromopentan-2-ol
  • An aqueous solution is 5.0% ethanoic acid (HC2H3O2) by mass and its density is 0.96 g mL−1 . What is the molar concentration of ethanoic acid in this solution?
    12 mol L−1
    4.8 mol L−1
    0.80 mol L−1
    0.087 mol L−1
  • Which represents the nucleophile in this reaction?
    A
  • Which of the following processes is the most endothermic?
    H2O(l)--> H2O(g)
    K + (g) + Cl− (g) --> KCl(s)
    F(g) + e−--> F − (g)
    Na(g) --> Na+ (g) + e−
  • On a phase diagram, the critical point lies at the end of the curve separating the _liquid_ phase and the _gas_ phase. At pressures and temperatures above the critical point, the substance is a
    supercritical fluid
  • Which of the following is the best reducing agent?
    Mg
    Cl2
    H2
    Cl-
  • Which alkene would you use to prepare (1-bromoethyl)cyclohexane
    ethenylcyclohexane
  • What type of reaction is this?
    an aldol reaction
    a Hoffmann rearrangement
    a Curtius rearrangement
    a Gabriel synthesis
  • Which base is most suitable to prepare a buffer solution with a pH = 11.00?
    ammonia (Kb = 1.8´10-5 )
    methylamine (Kb = 4.4´10-4 )
    pyridine (Kb = 1.7´10-9 )
    aniline (Kb = 4.0´10-10)
  • Which of the compounds E through K at the bottom of the page are enol tautomers of 2-butanone?
    JH
    EFJ
    KIG
    ABC
  • How many peaks would appear in the 13CNMR for the following compound? Atoms other than carbon and hydrogen are labeled.
    8
    9
    7
    6
  • Larger bond order means _________ bond strength.
    greater
  • What is the concentration of the solution that results from mixing 40.0 mL of 0.200 M HCl with 60.0 mL of 0.100 M NaOH?
    0.0600 M NaCl and 0.0200 M HCl
    0.0200 M NaCl and 0.0600 M HCl
    0.150 M NaCl
    0.0200 M NaCl and 0.0200 M HCl
  • A complex ion is a charged species consisting of a metal ion surrounded by
    ligands
  • This is the synthesis of methamphetamine. Intermediate A is an example of:
    imide
    imine
    enamine
    iminium ion
  • Which ion has the same electron configuration as Cl- ?
    Si4+
    P+
    F-
    Sc3+
  • How many resonance forms can be drawn for the NO3– ion?
    3
  • Which of the following has the greatest number of unpaired electrons in its ground electronic state?
    Cl
    Ti2+
    Zn2+
    Al
  • When equilibrium is established, which of the following will be true?
    [A] = [B] < [C]
    [A] = [B] = [C]
    [A] > [B] > [C]
    [A] < [B] < [C]
  • What is the pH of a solution made of 0.50 M acetic acid and 0.200 sodium acetate given the Ka of acetic acid is 1.8 x 10-5?
    4.34
  • which of the following group probably has the most unpleasant odour?
    butyl butanoate
    propanamine
    ethanol
    propanal
  • What is the valence electron for Polonium?
    6p4
    5p6
    7p3
    7p5
  • Calculate the heat released (in kJ mol-1 ) during this reaction, using the bond enthalpies given.
    563
    1160
    521
    296
  • Which statement comparing catalytic reactions to non-catalytic reactions is correct?
    The enthalpy of reaction of the catalytic reaction is small
    The activation energy of the catalytic reaction is smaller.
    The activation energy of the catalytic reaction is larger
    The enthalpy of reaction of the catalytic reaction is larger
  • What is the major product when 1-methylcyclohex-1-ene is reacted with hydrogen iodide
    1-iodo-1-methylcyclohexane
  • The electron configuration of a particular diatomic species is (σ2s)2(σ*2s)2(σ2p)2(π2p)2(π*2p)4. What is the bond order for this species?
    0
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