Vollhardt 6th Ed. (2010)
CH 2: Structure and Reactivity: Acids and Bases, Polar and Nonpolar Molecules

Solutions can be seen at mendelset.com/chapters/1132


  1. Problem # 286

    Draw the conjugate base forms of each acid listed below, then rank the acids in order or decreasing acidity (1 = most acidic).

    Explain your reasoning.

  2. Problem # 288

    Draw the conjugate base form of each acid listed below, then rank the acids in order or decreasing acidity (1 = most acidic).

    Explain your reasoning.

     

     

  3. Problem # 303

     Draw the conjugate base form of each acid listed below, then rank the acids in order or decreasing acidity (1 = most acidic).

    Explain your reasoning.

     

  4. Problem # 304

     Draw the conjugate base form of each acid listed below, then rank the acids in order or decreasing acidity (1 = most acidic).

    Explain your reasoning.

     

  5. Problem # 305

    Rank each group of acids in order of decreasing acidity. (1 = most acidic)

    Explain your reasoning. You will have to use more than one rule in your explanation (resonance, electronegativity, atomic radius, etc.). 

     

  6. Problem # 306

    Rank each group of acids in order of decreasing acidity. (1 = most acidic)

    Explain your reasoning. You will have to use more than one rule in your explanation (resonance, electronegativity, atomic radius, etc.). 

     

  7. Problem # 307

    Rank the group of molecules below in in order of decreasing basicity. (1 = most basic)

    Explain your reasoning.

  8. Problem # 308

     

    Rank the group of molecules below in in order of decreasing basicity. (1 = most basic)

    Explain your reasoning.

     

  9. Problem # 320

     

    Let's perform conformational analysis on 2-methylbutane along the C2-C3 bond. We'll use the energy chart given below.

     

    First, draw out the Newman projections along the C2-C3 bond, rotating the front carbon (C-2) by 60 degrees clockwise each time while keeping the back carbon (C-3) stationary.

    According to the table above, how much energy does each conformation "cost?"

     

    Second, make a plot of the total energy value for each Newman projection versus its dihedral angle.

     

  10. Problem # 535

    Rank the following anions in order of decreasing stability (1 = most stable)

  11. Problem # 540

     

    Rank the following anions in order of decreasing stability (1 = most stable)

  12. Problem # 697

    Rank the following compounds in order of decreasing boiling point.

    Also, make a guess about their relative solubilities in water. Explain your reasoning.

  13. Problem # 745

    The molecule below has five different types of hydrogens (A through E). Rank each in order of decreasing acidity.

    (1 = most acidic). Explain your reasoning.

  14. Problem # 1287

    Rank each set of compounds in order of decreasing boiling point (1 = highest boiling point):

    a) ethane, n-octane, n-pentane

    b) n-butane, 1-butanol, 1-chlorobutane.

    c) n-octane, 2-methylheptane, 2,5-dimethylhexane

     

    (Note that the n- prefix before an alkane just means that it's one chain, without any branching.)