# Textbook: Vollhardt 6th Ed. (2010)

## Individual Problems

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 # 308

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

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 # 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.

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 # 286

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

Problem # 288

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

Problem # 303

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

Problem # 304

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

Problem # 307

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

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.