2. Molecular Representations

Which has

g. the higher boiling point: 1-bromopentane or 1-chloropentane?

Which has

h. the higher boiling point: diethyl ether or butyl alcohol?

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

c. 1-bromobutane and 1-chlorobutane

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

b. isopropyl chloride and tert-butyl bromide

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

a. isopropyl bromide and n-butyl bromide

For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.

c. cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-ene

d. cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutane

For each pair of compounds, predict the one with a higher boiling point. Which compounds have zero dipole moments?

b. cis- or trans-2,3-dichlorobut-2-ene

For each pair of compounds, predict the one with a higher boiling point. Which compounds have zero dipole moments?

c. cyclohexene or 1,2-dichlorocyclohexene

Rank the boiling points of the following molecules. Explain your ranking ( 1 = highest bp; 3 = lowest bp ).

a. Which compound would you expect to have a greater dipole moment, methyl acetate or butanone?

b. Which would you expect to have a higher boiling point?

Imidazole boils at 257 °C, whereas N-methylimidazole boils at 199 °C. Explain the difference in boiling points.

Rank the following isomers in order of increasing boiling point, and explain the reasons for your order of ranking.

Identify the hydrogen bond donors and hydrogen bond acceptors in the following molecules.

(a)

Identify the hydrogen bond donors and hydrogen bond acceptors in the following molecules.

(d)

In each pair, which would you expect to have the higher melting point?

(b)