Introduction to Organic Chemistry Importance of carbon

Alkanes
Alkanes Nomenclature System Basis for all life.
Structural Isomers
Cycloalkanes
Form stable covalent bonds to other carbon
Reactions of Alkanes and Cycloalkanes atoms - catenation.
Alkyl Halides
Can form single, double and triple bonds.
Organic Long carbon chains can be produced.
Compounds Will bond with many other elements.
Alkanes A HUGE number of chemicals are possible.

Allotropic forms
of carbon
Elemental carbon exists in 4 forms.
Amorphous- no definite structure
Graphite- layered sheets of rings
Diamond- tetrahedral
Spherical- combination of rings

Classes of organic compounds Line representations

Molecular Formula C5H12
We commonly look at organic species
by class.
Possible line representations
Alkanes
simplest class of organic compounds CH3CH2CH2CH2CH3 n-pentane
contain only carbon and hydrogen CH3CH(CH3)CH2CH3 2-methylbutane
only have single bonds
(CH3)4C 2,2-dimethylpropane
methane ethane propane butane
H H H H H H H H H H All are structural isomers of C5H12.
H C H H C C H H C C C H H C C C C H
H H H H H H H H H H This system is used to show the arrangement
of atoms in a molecule in a single line.
Structural isomers Formula
Structural Formula
Compounds with the same number of
• Shows all atoms with bonds.
atoms and bonds but with different • Bonds are represented as lines.
arrangements. H H H
Example. Propane H C C C H

CH3CH2CH2CH2CH3 CH3CH(CH3)CH2CH3 H H H

CH3 Condensed formula

H2 H2
C C
• A type of line format.
CH CH3
H3C C CH3 H3C C • Shorthand way of writing formula.
H2 H2 • Lists all atoms in order and tells how they are
(CH3)4C bound together.
CH3
Example
H3C C CH3 Propane CH3CH2CH3
CH3

Shapes of organic Models

molecules Three dimensional representations
Properties of organic compounds are related to
their geometry. Ball and stick

Bond order will help to determine geometry.

• single bond = bond order of 1
• double bond = bond order of 2
• triple bond = bond order of 3

Models are useful to help see

these shapes.
Space filling

Ethane Hybridization
• Bond order = 1 You should be asking . . . .
• Single C-C bond
• Tetrahedral geometry “ If carbon has two s electrons and two p
electrons, how do we get a tetrahedral
shape? ”
• The reason is that the s and p orbitals will blend
together, giving us 4 equivalent orbitals.
• The s and p orbitals are very close in energy so
the four electrons spend time in the s and the 3
different p.
• This process is called hybridization.
 Hybridization Ethane sp3
hybrids

1s orbital
1 +3 4 of H
s p sp3
C ! bond C
In the case of a carbon that has 4 single
bonds, all of the orbitals are hybrids.

sp3
25% s and 75% p character We’ll look at other hybrids
in the next chapter.

Ethene Bond length and strength

• Bond order = 2
• Double C-C bond - sp2 hybrid bond length
• Planer geometry distance between two bonded atoms.
single bonds > double bonds > triple bonds
Ethyne bond strength
• Bond order = 3 energy necessary to break a chemical bond.
• Triple C-C bond - sp hybrid triple bonds > double bonds > single bonds
• Linear geometry

Classifying organic compounds Alkanes

Simplest members of the hydrocarbon
Classify compounds by functional group. family.

Functional group
• contain only hydrogen and carbon
Specific combination of atoms that gives a
• only have single bonds
known type of behavior All members have the general formula of
CnH2n+2
Hydrocarbons C and H only
Alcohols R-OH First four members of the alkanes
Acids R-COOH Name # of C Condensed formula
Amines R-NH2 Methane 1 CH4

Ketones R(C=O)R’
C=O Ethane 2 CH3CH3

Aldehydes R-CHO Propane 3 CH3CH2CH3

Butane 4 CH3CH2CH2CH3

R, R’ = any hydrocarbon chain. Called a homologous series

“Only differ by number of CH2 groups”
 Alkanes
Alkanes
Physical Properties
Non-polar molecules Name BP (oC) MP (oC) Density
Not soluble in water Methane -161.7 -182.6 0.424
Low density These
These gogo up
up
Ethane - 88.6 -172.0 0.546
Propane - 42.2 -187.1 0.582
Low melting point as the number
as the number Butane -0.5 -135.0 0.579
Low boiling point of
of carbons
carbons Pentane 36.1 -129.7 0.626
increase.
increase. Hexane 68.7 - 94.0 0.659
Heptane 98.4 - 90.5 0.684
Octane 125.6 - 56.8 0.703
Nonane 150.7 -53.7 0.718
Decane 174.0 -29.7 0.730

Organic nomenclature Naming alkanes

1. Find the longest carbon chain. Use as

Organic molecules can be very complex.
Naming system must be able to tell
• Number of carbons in the longest chain
• The location of any branches
• Where functional groups are (if any)
The IUPAC Nomenclature System provides
a uniform set of rules that we can follow.
base name with an ane ending.
2. Locate any branches on chain. Use
base names with a yl ending.
3. For multiple branch of the same type,
modify name with di, tri, ...
4. Number the location of each branch.
5. List multiple branches alphabetically -
the di, tri, ... don’t count..

Base names Length of carbon Naming alkanes

Prefix
chain
Meth 1
C-C-C-C-C-C
Eth 2
Prefixes are derived Six carbon atoms in the longest chain
Prop 3
from Greek (except use base name of hex
But 4
for ‘Non’ which is
Pent 5 All carbon and hydrogen with single bonds
from Latin.
Hex 6 use ane ending
Go figure? Hept 7
Oct 8 Name of compound is hexane
Non 9
Dec 10
 CH3 Examples
CH CH3 C-C-C-C-C-C
H3C C | | 3,5-dimethyl heptane
H2 C-C C
Longest C chain has 4 carbon - use but
3-ethyl-5-methylheptane C-C-C-C-C-C-C
All C and H with single bonds - use ane
| |
Parent name: butane C-C C
C-C-C-C C-C-C
CH3- on 2nd carbon - methyl | |
C-C-C-C-C-C-C
2-methylbutane | 2,3,3,7,8-pentamethyldecane
C

Another example Another example

(CH3)2CHCH2CH2CH(CH3)2
Name the following.

(CH3)2CHCH2CH2CH(CH3)2 C C
| |
This is a condensed structural formula. C-C-C-C-C-C
First convert it to a carbon skeleton,
leaving out the hydrogens - it may help. Now name it!

Even more examples

Another example

C C
| |
C-C-C-C-C-C 3-ethyl-2,2-dimethylhexane

1. Longest chain is 6 - hexane

2. Two methyl groups - dimethyl 4-propylheptane

3. Use 2,5-dimethylhexane
Even more examples Cycloalkanes
Cyclic alkanes of the general formula, CnH2n.

Named as the parent alkane but add cyclo-

cyclo-

4-methyldecane C-C
\ / cyclopropane
C Cyclic alkanes of the general formula,
CnH2n.
C-C
| | cyclobutane Named as the parent alkane but add
C-C cyclo-
C-C
/
C
\
C cyclohexane
• When they occur as a branch, use the
\ / same rules as with any branch.
C-C
• Cyclohexane as a branch would be
cyclohexyl.
2,2,4,4,6-pentamethylheptane

Cycloalkanes. cis and trans isomers

• The book discusses cis and trans isomers. We’ll
worry about it in the next chapter. Just a couple
of examples for now.

ethylcyclopentane CH3

H2C
CH
C
H2 H2
HC C
CH2

CH3
cycloheptane cyclohexane trans-1,4-dimethylcyclohexane

CH3

H2C
CH
1-cyclohexylheptane H3C
C
H2 H2 cis-1,4-dimethylcyclohexane
C C
H CH2

Sources of alkanes
Alkanes can be obtained by refinement or
Reactions of alkanes
hydrogenation of:
Halogenation
petroleum A reaction where a halogen
shale oil
coal replaces one or more hydrogens.

Low molecular weight alkanes can be

obtained directly from natural gas.
CH4(g) + Cl2(g) CH3Cl(g) + HCl(g)

Reactions of alkanes Used to prepare many solvents

Combustion
CH4(g) + 2 O2(g) CO2(g) + 2H2O(g)
• dichloromethane - paint stripper
Many alkanes are used this way - as fuels
• chloroform - used as anesthesia
Methane - natural gas • 1,2-dichloroethane - dry cleaning fluid
Propane - used in gas grills
Butane - lighters This is a substitution reaction
Gasoline - mixture of hydrocarbons
Alkyl halides Naming alkyl halides
Theses are alkanes with one or more
halogens in place of hydrogen.

A halogen The names used for halogens are

General formula R-X F, Cl, Br, I

Any alkane Halogen Name Symbol

chain fluorine fluoro -F
Structure and naming are chlorine chloro -Cl
similar to the alkanes. bromine bromo -Br
iodine iodo -I

!Follow the same system as Naming alkyl

with alkanes. halides Nomenclature examples
!Give the name and carbon CH3CHBrCH3
number for the halide just
like a side branch. 2-bromopropane
1-fluoro
fluoroethane 1-bromo
bromo-2-methylpentane CH3CH2C(CH3)ClCH2CH2CH3
C-C-F C-C-C C-C-C-C-C 3-chloro-3-methylhexane
| |

Cl C-Br CCl2F2
2-chloro
chloropropane
dichlorodifluoromethane
CH3C(CH3)ICH3
2-iodo-2-methylpropane

Examples Properties of alkyl halides

bromochloromethane
Melting points and Boiling points
• Higher than alkanes.
• Increase with MW and number of halides.
1-bromo-3-chloropropane
Solubility
• Not soluble in water.
• Soluble in nonpolar solvents like alkanes
other alkyl halides.
(chloromethyl)cyclopropane
 Classification of Classification of
alkyl halides alkyl halides
Based on the number of alkyl R-C-X R-C-R
groups attached to the carbon.
Primary Secondary |
Results in four classes X
- primary R
- secondary | Tertiary R Quaternary
- tertiary R-C-R |
- quaternary | R-C-R
This is true for other functional X |
groups as well R

Principal reaction type is halide exchange.

- a type of substitution reaction

halide exchange

CH3-Br + I- CH3-I + Br-

CH3-Br + OH- CH3-OH + Br-

Note!
Does not work with tertiary alkyl halides.

Reactions of alkyl halides