For each of the following compounds,

1. draw the Lewis structure.

2. show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.

3. estimate whether the compound will have a large, small, or zero dipole moment.

a. CH₃CH=NCH₃

b. CH₃CH₂OH

c. CBr₄

For each of the following compounds,

1. draw the Lewis structure.

2. show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.

3. estimate whether the compound will have a large, small, or zero dipole moment.

d.

For each of the following compounds,

1. draw the Lewis structure.

2. show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.

3. estimate whether the compound will have a large, small, or zero dipole moment.

e.

Sulfur dioxide has a dipole moment of 1.60 D. Carbon dioxide has a dipole moment of zero, even though C―O bonds are more polar than S―O bonds. Explain this apparent contradiction.

Which of the following pure compounds can form hydrogen bonds? Which can form hydrogen bonds with water? Which ones do you expect to be soluble in water?

a. (CH₃CH₂)₂NH

b. (CH₃CH₂)₃N

c. CH₃CH₂CH₂OH

d. (CH₃CH₂CH₂)₂OH

Which of the following pure compounds can form hydrogen bonds? Which can form hydrogen bonds with water? Which ones do you expect to be soluble in water?

e. CH₃(CH₂)₃CH₃

f. CH₂=CH—CH₂CH₃

g. CH₃COCH₃

h. CH₃CH₂COOH

Predict which member of each pair is more soluble in water. Explain your prediction.

(a)

(b)

Predict which member of each pair is more soluble in water. Explain your prediction.

(c)

(d)

Predict which member of each pair is more soluble in water. Explain your prediction.

(e)

(f)

Diethyl ether and butan-1-ol are isomers, and they have similar solubilities in water. Their boiling points are very different, however. Explain why these two compounds have similar solubility properties but dramatically different boiling points.

N-Methylpyrrolidine has a boiling point of 81 °C, and piperidine has a boiling point of 106 °C.

b. Tetrahydropyran has a boiling point of 88 °C, and cyclopentanol has a boiling point of 141 °C. These two isomers have a boiling point difference of 53 °C. Explain why the two oxygen-containing isomers have a much larger boiling point difference than the two amine isomers.

N-Methylpyrrolidine has a boiling point of 81 °C, and piperidine has a boiling point of 106 °C.

c. N,N-Dimethylformamide has a boiling point of 150 °C, and N-methylacetamide has a boiling point of 206 °C, for a difference of 56 °C. Explain why these two nitrogen-containing isomers have a much larger boiling point difference than the two amine isomers. Also explain why these two amides have higher boiling points than any of the other four compounds shown (two amines, an ether, and an alcohol).

Predict which compound in each pair has the higher boiling point. Explain your prediction.

(a) CH₃CH₂OCH₃ or CH₃CH(OH)CH₃

(b) CH₃CH₂CH₂CH₃ or CH₃CH₂CH₂CH₂CH₃

Predict which compound in each pair has the higher boiling point. Explain your prediction.

(c) CH₃CH₂CH₂CH₂CH₃ or (CH₃)₂CH₂CH₂CH₃

(d) CH₃CH₂CH₂CH₂CH₃ or CH₃CH₂CH₂CH₂CH₂Cl

Predict which compound in each pair has the higher boiling point. Explain your prediction.

(e)

(f)

Rank the following species in order of increasing acidity. Explain your reasons for ordering them as you do.

HF NH₃ H₂SO₄ CH₃OH CH₃COOH H₃O⁺ H₂O

All of the following compounds can react as acids. Without using a table of acidities, rank them in order of increasing acidity. Explain your ranking.

a. CH₃CH₂SO₃H

b. CH₃CH₂OH

c. CH₃CH₂COOH

d. CH₃CHClCOOH

e. ClCH₂CH₂COOH

Rank the following species in order of increasing basicity. Explain your reasons for ordering them as you do.

NH₃ CH₃O^– H₂O CH₃COO^– NaOH NH₂^– HSO₄^–

The K_a of phenylacetic acid is 5.2 × 10⁻⁵, and the pK_a of propionic acid is 4.87.

a. Calculate the pK_a of phenylacetic acid and the K_a of propionic acid.

b. Which of these is the stronger acid? Calculate how much stronger an acid it is.

The K_a of phenylacetic acid is 5.2 × 10⁻⁵, and the pK_a of propionic acid is 4.87.

c. Predict whether the following equilibrium will favor the reactants or the products.

The following compound can become protonated on any of the three nitrogen atoms. One of these nitrogens is much more basic than the others, however.

a. Draw the important resonance forms of the products of protonation on each of the three nitrogen atoms.

The following compound can become protonated on any of the three nitrogen atoms. One of these nitrogens is much more basic than the others, however.

b. Determine which nitrogen atom is the most basic.

The following compounds are listed in increasing order of acidity. In each case, the most acidic proton is shown in red.

b. Explain why X is a stronger acid than W.

c. Explain why Y is a stronger acid than X.

d. Explain why Z is a stronger acid than Y.

Predict the products of the following acid–base reactions.

(a) H₂SO₄ + CH₃COO^– ⇌

(b) CH₃COOH + (CH₃)₃N: ⇌

Hydrogen peroxide (HOOH) has a pK_a of 11.6, making it roughly 10,000 times as strong an acid as water (pK_a = 15.7). Explain why H₂O₂ is a stronger acid than H₂O.

Peroxyacetic acid (pK_a = 8.2) is a much weaker acid than acetic acid (pK_a = 4.74). Explain why peroxyacetic acid is a weaker acid than acetic acid.

Predict the products of the following acid–base reactions.

(c)

(d)

Predict the products of the following acid–base reactions.

(e) H₂O + NH₃ ⇌

Predict the products of the following acid–base reactions.

(f)

Predict the products of the following acid–base reactions.

(g) HCOOH + CH₃O^– ⇌