Textbook: Brown 6th Ed. (2011)

Individual Problems

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!

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.)

Problem # 309

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

Problem # 310

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

Problem # 311

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

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!

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!

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!

Problem # 569

Draw all resonance forms for each species.

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

Problem # 580

Draw all resonance forms for each species.

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

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.

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.

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.