Textbook: Solomons 10th Ed. (2009)

Remember the rules of what gives compounds a higher boiling point (and melting point):

Van der Waals Forces

More electrons = more Van der Waals interactions = higher boiling point

So in general, the more "stuff" in a molecule (the higher the molecular weight), the higher its b.p. Example: C₁₀H₂₂ will have a higher b.p. than C₅H₁₂.

How to remember this trend? What do you grill with? propane gas. (C₃H₈)

What's in a lighter? butane liquid (C₄H₁₀)

Hydrogen Bonding

Compounds that can hydrogen bond have higher b.p./m.p/ than those that don't.

Compounds can hydrogen bond is they have a N, O, or F bonded directly to an H.

In organic chemistry, the best examples are alcohols (ROH) and amines (RNH₂).

Branching

Branching makes it harder for molecules to pack together, which makes it harder to form Van der Waals interactions, and so tends to lower b.p./m.p.

a) (highest b.p.) n-octane > n-pentane > ethane (lowest b.p.)

Reason: octane has the most "stuff" (higher molecular weight).

b) 1-butanol > 1-chloroethane > n-butane

Reason: 1-butanol can hydrogen bond. 1-chloroethane has a higher molecular weight than n-butane.

c) n-octane > 2-methylheptane > 2,5-dimethylhexane

Reason: Branching. n-octane has no branching. 2,5-dimethylhexane has the most branching. Notice that each compound has the same molecular formua- C₈H₁₈. (and therefore the same weight).