Brown 6th Ed. (2011)
CH 1: Covalent Bonding and Shapes of Molecules

Solutions can be seen at mendelset.com/chapters/1158


  1. Problem # 309

    Convert each formula to a carbon skeleton diagram, or vice-versa.

     

  2. Problem # 310

    For each molecule, determine the formal charge of the indicated atom.

     

  3. Problem # 311

    For each molecule below, draw in all implied lone pairs and/or protons (hydrogens) based on the formal charge shown.

     

  4. Problem # 312

    Draw all possible resonance forms for each structure below. Use curved arrows.

    Note that some structures only show charge, and not implied protons or lone pairs!

     

  5. Problem # 313

    Draw all possible resonance forms for each structure below. Use curved arrows.

    Note that some structures only show charge, and not implied protons or lone pairs!

     

     

  6. Problem # 314

    Draw all possible resonance forms for each structure below. Use curved arrows.

    Note that some structures only show charge, and not implied protons or lone pairs!

  7. Problem # 315

     

    Draw all possible resonance forms for each structure below. Use curved arrows.

    Note that some structures only show charge, and not implied protons or lone pairs!

     

  8. Problem # 569

    Draw all resonance forms for each species. 

    For the anion and cation species, used curved arrows. For the radical species, use hooks.

  9. Problem # 580

    Draw all resonance forms for each species.

    For the anion and cation species, used curved arrows. For the radical species, use hooks.

  10. 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.

  11. Problem # 755

    The nitrosyl cation is shown below. Also shown are several proposed resonance arrows, only one of which is correct.

    Draw the resonance forms that would follow from each set of arrows, and include formal charges. Which one is the correct resonance form? Explain your reasoning.

  12. Problem # 1286

    For the molecule shown below, indicate the hybridization (sp3, sp2, sp, etc.) of atoms A through H, and the bond angles of X, Y, and Z.

  13. 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.)