Exercise

a) One stereoisomer of 1,4-dibromocyclohexane has a

melting point of 113oC; the other isomer melts below
0oC. Draw both structures and assign melting points to
the structures. Justify your choice.

b) Which has the higher melting point, hexane or

cyclohexane? Explain your choice.

c) Cyclopentanethiol has a markedly

Lower melting point than cyclopentanol even though it
has a higher molecular weight. Explain.
1
There is a 20oC difference in the boiling points of
cyclohexane and 1,4-dioxacyclohexane (commonly called
1,4-dioxane). Which boils higher? Explain.

2
Exercise 4.3
a) Is cyclohexane more or less soluble in water than
1,4-dioxacyclohexane (more commonly called 1,4-
dioxane)? Explain.

b) Which of the two following compounds is more

soluble in pentane? (Hint: Be sure to draw a Lewis
structure of each.)

c)Is methyl acetate more or less soluble in pentane

than is propanoic acid? Explain.