Hydrocarbons & Allotropes of Carbon

CHEM 357 Lecture 4 2.1-2.8 & pages 102-103, 105 & 138139.

Classes of Hydrocarbons

Hydrocarbons

Aliphatic

Aromatic

Alkanes

Alkenes

Alkynes

A straight chain hydrocarbon has the molecular formula C4H6 how many double () bonds does it contain? A0 B1 C2 D3 E4 F Need More
Information

Draw potential structures that fit this molecular formula

Introduction to Alkanes: Methane, Ethane, and Propane

Methane
CnH2n+2

(CH4)

CH4

Ethane

(C2H6) CH3CH3

Propane

(C3H8) CH3CH2CH3

bp -160C

bp -89C

bp -42C

Isomeric Alkanes: The Butanes

n-Butane Isobutane

CH3CH2CH2CH3 (CH3)3CH

bp -0.4C

bp -10.2C

Higher n-Alkanes

CH3CH2CH2CH2CH3 n-Pentane (BP 36.1C)

CH3CH2CH2CH2CH2CH3
n-Hexane (BP 68-69C)

CH3CH2CH2CH2CH2CH2CH3 n-Heptane (BP 98C)

How Many Isomers?

The number of isomeric alkanes increases as the number of carbons increase

Number of Constitutionally Isomeric Alkanes

CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 1 1 1 2 3 5 9 C8H18 C9H20 C10H22 C15H32 C20H42 C40H82 18 35 75 4,347 366,319 62,491,178,805,831

Physical Properties of Alkanes and Cycloalkanes

A ___________ is a change in the form of matter but not in its chemical identity
e.g.

Change of Phase (solid/liquid/gas) Solvation/dissolution A ___________ occurs whenever compounds are formed or decomposed

Boiling Point
Need to overcome inter-molecular forces (non-covalent interactions)

Governed by strength of intermolecular attractive forces Alkanes are nonpolar, so dipole-dipole and dipole-induced dipole forces are absent Only forces of intermolecular attraction are _____________________forces.

Explain how an induced dipole-induced dipole arises

Sources of Alkanes and Cycloalkanes Fractional distillation of crude oil, Fractional tower

25-95 C

70-200 C
100-150 C 150-230 C

200-300 C
300-400 C 350-450 C 400-500+ C

http://science.howstuffworks.com/environmental/energy/oil-refining5.htm http://www.gcsescience.com/o5.htm

 Gasoline is the most valuable fraction of crude oil refining, however only constitutes ~25% of the crude oil. Why higher boiling point fractions are cracked into lower boiling point fractions. Why lower boiling point fractions are reformed to make higher mw hydrocarbons.

Converting other fractions to gasoline

Cracking converts high molecular weight hydrocarbons to more useful, low molecular weight ones Types of Cracking: -Thermal Cracking (750-900C, 700 kPa) -makes ethane & propane -Catalytic Cracking (no O2, 500C & Zeolite) -makes 3-8 Carbons (propane to octane) -Hydrocracking (5000 kPa, H2 and Pt catalyst) -makes Kerosene & gasoline -Thermal Steam Cracking (850C, no O2) -makes alkenes for plastics & aromatics -higher temps means more unsaturated HCs

Petroleum Refining
Reforming
increases branching of hydrocarbon chains branched hydrocarbons have better burning characteristics for automobile engines More highly branched structures burn smoothly, while unbranched hydrocarbons tend to explode causing the drive piston forward violently, creating knocks. Why do branched hydrocarbons burn better?

Octane number
Scale to set up to evaluate burning of gasoline

Octane number 0

Gas at the pump is 87, 87% isooctane & 13% heptane What does unleaded mean?
Aromatics also have high octane ratings

Octane number 100

Explain how chain length and the degree of branching in alkanes have an affect on boiling point

..

Boiling Points

Heptane bp 98C

Octane bp 125C

Nonane bp 150C

Boiling Points

Octane: bp 125C 2-Methylheptane: bp 118C 2,2,3,3-Tetramethylbutane: bp 107C

The Power of Van der Waals Interactions

Gecko foot
http://academic.udayton.edu/NIRT/gecko.htm

A toe of gecko foot contains hundreds of thousands of setae and each seta contains hundreds of spatulae

Using Physical Change as a Power Source

Using Physical Change as a Power Source

http://straction.wordpress.com/how-the-steam-engine-of-the-locomotive-works/

Using Physical Change as a Power Source

http://straction.wordpress.com/how-the-steam-engine-of-the-locomotive-works/

Why Choose Water ?

Burn Fuel Heat Liquid Water

Expand to Gas Phase (i.e. Steam) Push a piston

Physical Properties of Molecules

The physical properties of a molecule are encoded by the chemical properties
E.g. melting point, boiling point, solubility

What Properties are Important in Determining Boiling Point ? Already seen hydrocarbons:

Hexane

Pentane

2-Methylbutane

69C

36C

28C

Boiling Points
O OH O

OH
28C 31C 80C 99C 141C

Boiling Points
O OH O

OH
28C 31C 80C 99C 141C

Allotropes of Carbon
Carbon atoms form strong bonds with itself.
Bucky ball diamond

Carbon nanotubes graphite

31

 Graphene
A single layer of graphite Atomic scale chicken wire A single layer was first isolated by using tape to pull off thinner and thinner layers Tape was then dissolved in acetone. Done 2004, noble prize 2010.

Applications . . .