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    Chapter 2 Practice

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    cwod
    This document contains practice problems related to acid-base chemistry and organic structures. It includes 25 questions about identifying acids and bases, drawing structures, assigning formal charges and determining polarity. It also contains 10 additional questions involving curved arrow notation, acidity constants, and identifying reactants and products in acid-base reactions.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd

    Chapter 2 Practice

    Uploaded by

    cwod
    88 views11 pages
    This document contains practice problems related to acid-base chemistry and organic structures. It includes 25 questions about identifying acids and bases, drawing structures, assigning formal charges and determining polarity. It also contains 10 additional questions involving curved arrow notation, acidity constants, and identifying reactants and products in acid-base reactions.

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    Chapter 2 practice

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    This document contains practice problems related to acid-base chemistry and organic structures. It includes 25 questions about identifying acids and bases, drawing structures, assigning formal charges and determining polarity. It also contains 10 additional questions involving curved arrow notation, acidity constants, and identifying reactants and products in acid-base reactions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    88 views11 pages

    Chapter 2 Practice

    Uploaded by

    cwod
    This document contains practice problems related to acid-base chemistry and organic structures. It includes 25 questions about identifying acids and bases, drawing structures, assigning formal charges and determining polarity. It also contains 10 additional questions involving curved arrow notation, acidity constants, and identifying reactants and products in acid-base reactions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 11

    Chapter 2 Practice and Review

    1. Convert the following structure into a skeletal drawing.

    2. Convert the following structure into a skeletal drawing.

    Structural
    Consider the structural representation below to answer the following questions.

    3. Refer to Structural. This skeletal structure corresponds to the molecular formula:

    a. C5H6O6
    b. C7H10O6
    c. C6H6O6
    d. C6H8O6
    4. Refer to Structural. Show how many hydrogen atoms are bonded to each carbon in Vitamin C.
    Formal Charges
    Calculate the formal charges on the indicated atoms in each compound below.

    5. Refer to Formal Charges. The formal charge on phosphorous is __________.


    6. Refer to Formal Charges. The formal charge on oxygen is __________.
    7. Refer to Formal Charges. The formal charge on carbon is __________.
    8. Refer to Formal Charges. The formal charge on oxygen is __________.

    Phenylalanine
    Phenylalanine is an amino acid that is essential to human nutrition. The representation below shows the
    structure of phenylalanine at physiological pH. Consider this structure to answer the following questions.

    9. Refer to Phenylalanine. Assign any formal charges to atoms in this representation of phenylalanine.
    10. Refer to Phenylalanine. The oxygen atom labeled A. has __________ non-bonding electrons.
    11. Refer to Phenylalanine. The oxygen atom labeled B. has __________ bonding electrons.
    12. Use the convention and the crossed arrow ( ) to show the direction of the expected polarity of
    the indicated bond in the following compound.

    The C−F bond in fluorobenzene,


    13. Use the convention and the crossed arrow ( ) to show the direction of the expected polarity of
    the indicated bond in the following compound.

    The C−Si bond in tetramethylsilane, (CH3)4Si


    14. Use the convention and the crossed arrow ( ) to show the direction of the expected polarity of
    the indicated bond in the following compound.

    The C−O bond in furan,


    15. Label the acid and base in each reaction.

    16. Label the acid and base in each reaction.

    Equation 2-1
    Refer to the following equation to answer the questions below. Place the letter corresponding to the correct
    answer in the blank.

    17. Refer to Equation 2-1. The strongest Brønsted-Lowry acid in the equation is __________.
    18. Refer to Equation 2-1. The strongest Brønsted-Lowry base in the equation is __________.
    19. Refer to Equation 2-1. Will this reaction take place as written? Explain.
    20. An acid with a low pKa:

    a. is a weak acid
    b. is a strong acid
    c. has a weak conjugate base
    d. both b and c

    Cocaine
    The following questions refer to cocaine, whose skeletal structure is shown below.

    21. Refer to Cocaine. The number of hydrogens bonded to this carbon is __________.
    22. Refer to Cocaine. The number of hydrogens bonded to this carbon is __________.
    23. Refer to Cocaine. The number of hydrogens bonded to this carbon is __________.
    24. Refer to Cocaine. The molecular formula for cocaine is __________.
    25. Circle all the Lewis bases in the group of compounds below.

    26. Put a box around all the Lewis acids in the group of compounds below.

    27. Draw two resonance structures for the species below.

    28. Draw two resonance structures for the species below.

    29. Draw two resonance structures for the species below.

    Acidity Constants
    Consider the acidity constants below to answer the following questions.
    30. Refer to Acidity Constants. Which acid above will be almost completely deprotonated by NaOH?
    31. Refer to Acidity Constants. Which acid has the strongest conjugate base?
    32. Explain why phenol has a much lower pKa than ethanol.

    Reaction 2-1
    Consider the reaction below to answer the following questions.

    33. Refer to Reaction 2-1. Using the curved arrow formalism, show the flow of electrons for this reaction.
    34. Refer to Reaction 2-1. Label the acid and the base in the reaction.

    Indole
    Indole is pleasant smelling in highly dilute solutions and had been used in perfumery. Use the structure of
    indole, below, to answer the following questions.

    35. Refer to Indole. Indole can function as a Bronsted-Lowry acid in the presence of strong bases. Formulate a
    reaction, showing electron flow with arrows, that demonstrates this reactivity of indole.
    36. Refer to Indole. Indole can function as a Lewis base in the presence of strong acid. Formulate a reaction,
    showing electron flow with arrows, that demonstrates this reactivity of indole.

    Reaction 2-2
    Consider the acid-base reaction below to answer the following questions.

    37. Refer to Reaction 2-2. Using the curved arrow formalism, show the flow of electrons for this reaction.
    38. Refer to Reaction 2-2. Write the products of this Lewis acid - base reaction.
    Chapter 2 Practice
    Answer Section

    PROBLEM

    1. ANS:

    PTS: 1
    2. ANS:

    PTS: 1
    3. ANS:
    d

    PTS: 1
    4. ANS:

    PTS: 1
    5. ANS:
    +1

    PTS: 1
    6. ANS:
    -1

    PTS: 1
    7. ANS:
    -1

    PTS: 1
    8. ANS:
    +1

    PTS: 1
    9. ANS:

    PTS: 1
    10. ANS:
    four

    PTS: 1
    11. ANS:
    two

    PTS: 1
    12. ANS:

    PTS: 1
    13. ANS:

    PTS: 1
    14. ANS:

    PTS: 1
    15. ANS:

    PTS: 1
    16. ANS:

    PTS: 1
    17. ANS:
    D

    PTS: 1
    18. ANS:
    C

    PTS: 1
    19. ANS:
    No, the reaction will not take place as written because the strongest acid reacts with the strongest base to give
    the weakest conjugate acid and the weakest conjugate base. D (pKa = 15.7) is a stronger acid than A (pKa =
    18).

    PTS: 1
    20. ANS:
    d

    PTS: 1
    21. ANS:
    two

    PTS: 1
    22. ANS:
    one

    PTS: 1
    23. ANS:
    zero

    PTS: 1
    24. ANS:
    C17H21NO4

    PTS: 1
    25. ANS:

    PTS: 1
    26. ANS:
    PTS: 1
    27. ANS:

    PTS: 1
    28. ANS:

    PTS: 1
    29. ANS:

    PTS: 1
    30. ANS:
    phenol

    PTS: 1
    31. ANS:
    Ethanol is the weakest acid (largest pKa) so its conjugate base, ethoxide, CH3CH2O−, will be the strongest
    base.

    PTS: 1
    32. ANS:
    Phenol is more acidic (has a lower pKa) than ethanol because the phenoxide anion is resonance stabilized by
    the pi electrons in the ring. Sharing (delocalizing) the negative charge on oxygen with the three ring carbons
    stabilizes the phenoxide anion relative to undissociated phenol.

    Ethoxide anion has no resonance stabilization. The negative charge is borne fully by oxygen.
    PTS: 1
    33. ANS:

    PTS: 1
    34. ANS:

    PTS: 1
    35. ANS:

    PTS: 1
    36. ANS:

    PTS: 1
    37. ANS:

    PTS: 1
    38. ANS:
    PTS: 1

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