# Textbook: McMurry 8th 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 # 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. 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. 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. 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. Problem # 307

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

Explain your reasoning. Problem # 308

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

Explain your reasoning. Problem # 535 Rank the following anions in order of decreasing stability (1 = most stable) Problem # 540

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