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Old End of CCC final review

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  • In comparing Fischer projections, which of the following are allowed rotations in the plane of the page?
    90°
    109°
    270°
    180°
  • Which statements regarding alloys are correct?
    I and II only
    II and III only
    I and III only
    I, II and III
  • How many covalent bonds does graphite have?
    3
  • What reagent(s) can be used for this reaction?
    BH3, THF H2O2, NaOH, H2O OR just water in acid
  • Which alkene would you use to prepare (1-bromoethyl)cyclohexane
    ethenylcyclohexane
  • Q and Z are cyclic examples of:
    hemialditols
    alditols
    hemiacetals
    acetals
  • What is the major functional group shown here?
    Primary amine
  • what reagent can be used for this reaction?
    O3 Zn, H3O+
  • What are the reagents?
    1. NaNH2, NH3 2. CH3CH2I
  • What do you see in a mass spec if there is an alcohol
    M-18 and also alpha cleavage
  • Unknown element W has 2 valence electrons. Unknown element X has 7 valence electrons. Which formula shows the most likely outcome when elements W and X react?
    WX2
  • How many resonance forms can be drawn for the NO3– ion?
    3
  • The process by which anomer Q is converted into a mixture of both anomers is called:
    mutarotation.
    anomeric rotation
    glycosidation
    pyranorotation.
  • Which of the molecules obeys the octet rule?
    O3
    BH3
    NO2
    PCl5
  • 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
  • What type of reaction is this?
    addition/hydration
  • . Compound Z is:
    the α-anomer
    the D-anomer
    the β-anomer
    the L-anomer
  • 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
  • Which of the following would you expect to have the highest melting point?
    hydrogen chloride
    dinitrogen oxide
    phosphorous trichloride
    magnesium fluoride
  • Which molecule is most polar?
    CClF 3
    CHF 3
    CF 4
    CCl 4
  • What is the molecular formula of this natural product?
    C13H10
  • What is the electron configuration of the Mn(II) ion?
    [Ar] 3d5
  • What is the major product when 1-methylcyclohex-1-ene is reacted with hydrogen iodide
    1-iodo-1-methylcyclohexane
  • The stereochemical configuration of the C4-C5 alkene is
    Z
  • Although not always evident in an IR spectrum, which peak in the IR spectrum below might be due to the C—O stretch of an ether?
    2
    1
    3
    4
  • Which reagent would be used
    NaOCH3, CH3OH
    warm H2SO4/H2O
    Hg(O2CCF3)2, CH3OH
    NaH, then CH3I
  • What is a major peak of an alcohol in IR?
    broad peak at around 3400
  • What is the molecular geometry of the carbonate ion? What would be the angles?
    trigonal planar; 120 degrees
  • How many d electrons are present on the metal ion in the complex ion FeCl64–?
    6
  • This Williamson ether synthesis reaction is mechanistically
    SN1 process
    SN2 process
    E2 process
    E1 process
  • The hybridization of the central atom in XeF5+ is:
    dsp3
    sp2
    d2sp3
    sp3
  • Name the 2 products
    iodoethane and butan-2-ol
  • Which of these compounds would you expect to be water soluble?
    propanoic acid and naproxen
  • Which reagent would be used
    NaH, then CH3I
    NaOCH3, CH3OH
    m-ClC6H4CO3H
    Hg(O2CCF3)2, CH3OH
  • Name the following with IUPAC naming
    (1-methylethyl) benzene
  • Are these: conformational isomers, stereoisomers, constitutional isomers OR identical
    identical
  • This is the amino acid valine. Is it chiral? Explain
    yes, the carbon where NH2 is.
  • Which reagent would be used
    NaOCH3, CH3OH
    CH3MgBr in ether, then H3O+
    Hg(O2CCF3)2, CH3OH
    NaH, then CH3I
  • What is the bond order of O2–
    1.5
  • 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: a. is a racemate. b. does not have chiral centers. c. is a meso compound
    all are possible
  • What reagent can be used
    CH2I2, Zn(Cu)
  • Larger bond order means _________ bond strength.
    greater
  • Which reagent would be used
    NaOCH3, CH3OH
    PCC, CH2Cl2
    warm H2SO4/H2O
    CH3MgBr in ether, then H3O+
  • Consider the acidity constants below to answer the following question. Which acid will be almost completely deprotonated by NaOH?
    phenol
  • How many chirality centers are present?
    4
    1
    3
    2
  • What are the reagents?
    1. BH3, (THF) 2. H2O2, (NaOH, H2O)
  • How many bridgehead carbons are there in camphor?
    2
  • What m/z ratio range might be common to many substituted benzene compounds?
    26-38
    less than 59
    81-88
    72-77
  • The stereochemical configuration at C3 (one answer to be given only)
    R
  • 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
  • If four orbitals on one atom overlap four orbitals on a second atom, how many molecular orbitals will form?
    8
  • 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
  • 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
  • Which reagent would be used
    CH3MgBr in ether, then H3O+
    warm H2SO4/H2O
    NaH, then CH3I
    NaOCH3, CH3OH
  • A complex ion is a charged species consisting of a metal ion surrounded by
    ligands
  • The hybridization of the nitrogen atom
    sp3
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