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    Organic Chemistry Prelim Exam Part 1

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    Nathan Ray Alim
    The document contains an organic chemistry exam covering various topics: [1] Drawing Lewis structures and calculating formal charges for various molecules and ions [2] Ranking acids and bases by Brønsted acidity/basicity based on pKa values [3] Identifying the strongest Lewis acids and bases [4] Determining whether reactions will proceed completely, partially or not at all based on pKa values [5] Drawing resonance structures and molecular orbital diagrams

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    Organic Chemistry Prelim Exam Part 1

    Uploaded by

    Nathan Ray Alim
    303 views1 page
    The document contains an organic chemistry exam covering various topics: [1] Drawing Lewis structures and calculating formal charges for various molecules and ions [2] Ranking acids and bases by Brønsted acidity/basicity based on pKa values [3] Identifying the strongest Lewis acids and bases [4] Determining whether reactions will proceed completely, partially or not at all based on pKa values [5] Drawing resonance structures and molecular orbital diagrams

    Original Description:

    Organic Chemistry Reviewer Questions

    Original Title

    Prelim OrgChem 1

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    The document contains an organic chemistry exam covering various topics: [1] Drawing Lewis structures and calculating formal charges for various molecules and ions [2] Ranking acids and bases by Brønsted acidity/basicity based on pKa values [3] Identifying the strongest Lewis acids and bases [4] Determining whether reactions will proceed completely, partially or not at all based on pKa values [5] Drawing resonance structures and molecular orbital diagrams

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    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    303 views1 page

    Organic Chemistry Prelim Exam Part 1

    Uploaded by

    Nathan Ray Alim
    The document contains an organic chemistry exam covering various topics: [1] Drawing Lewis structures and calculating formal charges for various molecules and ions [2] Ranking acids and bases by Brønsted acidity/basicity based on pKa values [3] Identifying the strongest Lewis acids and bases [4] Determining whether reactions will proceed completely, partially or not at all based on pKa values [5] Drawing resonance structures and molecular orbital diagrams

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    © All Rights Reserved
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    Download as docx, pdf, or txt
    of 1

    Organic Chemistry Prelim Exam Part 1

    A. Formal charges. Draw the Lewis dot structures of the following molecules/ions 4) Reaction of potassium hydroxide and tertiary butanol
    and calculate the formal charge of the atoms inside the parenthesis.
    1) Hypochlorite ion (Cl, O) pKa of H2O = 15.7 pKa of tert-butanol = 17
    2) Nitrogen monoxide (N, O)
    5) Reaction of tert-butyllithium with ammonia
    B. Brønsted acidity. Draw the structure of the strongest Brønsted acid, and arrange
    the following in order of INCREASING Brønsted acidity. Use "<" ('less than’) sign to
    assign the lower vs. higher (e.g. A < B < C < D). + Li+
    1) A. Benzoic acid, B. p-nitrobenzoic acid, C. m-nitrobenzoic acid, D. o-nitrobenzoic acid pKa of tert-butane = 53 pKa of NH3= 38
    2) A. Ethyne, B. ethylene (ethene), C. ethane, D. benzene

    C. Brønsted basicity. Draw the structure of the strongest Brønsted base, write the G. Resonance structures.
    pKa of its conjugate acid, and arrange the following in order of increasing Brønsted 1) Draw the resonance structures of nitrobenzene. (5 pts.)
    basicity. (Refer to Evan's pKa table if applicable). Use "<" sign. 2) Draw the resonance structures of phenol. (5 pts.)
    1) A. NaOMe, B.tBuOK, C. NaOH, D. NaNH2
    2) A. NaNH2, B. KHMDS, C. LDA, D. tBuLi
    H. Molecular orbital
    D. Lewis acidity. Draw the structure of the strongest Lewis acid, and arrange the Draw the molecular orbital diagram of ethene (H2C=CH2).
    following in order of increasing Lewis acidity. Use "<" sign.
    1) A. NaCl, B. CaCl2, C. AlCl3, D. TiCl4
    2) A. BCl3, B. AlCl3, C. GaCl3, D. InCl3 Bonus question: Which of the following has the highest Lewis acidity (partial positive
    charge)? Why? BF3, BCl3, BBr3, BI3
    E. Lewis basicity. Draw the structure of the strongest Lewis base, and arrange the
    following in order of increasing Lewis basicity. Use "<" sign.
    1) A. NaOH, B. LiHMDS, C. tBuOK, D. LDA
    2) A. Acetone, B. hexafluoroacetone, C. 1,1-difluoroacetone, D. bromoacetone

    F. Indicate whether the given reaction PROCEEDS COMPELETELY, PROCEEDS


    PARTIALLY, or DOES NOT PROCEED. (10 pts.)

    1) Reaction of carbonate with methanol

    pKa of HCO3– = 10 pKa MeOH = 15.5

    2) Reaction of methoxide with bicarbonate

    pKa MeOH = 15.5 pKa of HCO3– = 10

    3) Reaction with propyne and sodium amide

    pKa = 25 pKa of NH3 = 38

    Note: 1) Use "<" sign for arranging compounds in order of increasing Brønsted/Lewis acidity or basicity, or boiling point. (e.g. EtOH < H2O < AcOH)
    2) KHMDS = potassium hexamethyldisilazide, LDA = lithium N,N-diisopropylamide, DMAP = dimethyl aminopyridine, DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, DABCO = 1,4-
    diazabicyclo[2.2.2]octane, Cy2NEt = dicyclohexylethylamine, iPr2NEt = diisopropylethylamine

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