E2 Organic Chemistry

Organic
Chemistry
The Chemistry
of Carbon
Table of Contents
Organic Chemistry
Distilling Crude Oil

Methane
Ethane
Propane
Butane
Pentane
Alkanes
Alcohols
Aldehydes and Ketones
Ethers
Functional Groups
Alkenes & Alkynes

Cycloalkanes
Benzene
Aromatic Hydrocarbons
Carboxylic Acids
Classes of Organic
Compounds
Chirality
Polymers
Organic Chemistry
Organic Chemistry: The chemistry of carbon
and carbon-based compounds
Organic Chemistry in everyday life:
Smells & tastes: fruits, chocolate, fish, mint
Medications: aspirin, Tylenol, decongestants, sedatives
Addictive substances: caffeine, nicotine, alcohol, narcotics
Hormones/Neurotransmitters: adrenaline, epinephrine
Food: carbohydrates, protein, fat
Genetics: DNA, RNA
Consumer products: plastics, nylon, rayon, polyester
Friedrich Whler
Made the first organic compound from

non-living substances. Shot down the
Vital Force idea of organic substances.
Fractional
Distillation
of Crude Oil
Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 429
Energy Sources
in United States
100
91
Percent
80
71
70
60
58
50
40
40
21
20
26
20
10
16
10
1850
Wood
1900
Coal
Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 648
1940
1980
Petroleum / natural gas
1990
Hydro and nuclear

Separate fractions
based on differences
in boiling point.
American Petroleum Usage

AMERICAN PETROLEUM USAGE
A Lesson in Economics
1 Barrel of Petroleum
93% Energy Marketplace

7% Materials Marketplace
(42 gallons)
42 Gallons of Crude Petroleum
36 Gallons Fuel
At $3.00 per gallon
36 Gallons Fuel
19 Gallons Gasoline
(11 Gallons in 1920)
$108.00
OR
7% (3 Gallons Crude)
At $20.00 per shirt
100 Nylon Shirts

$2000.00
Entrepreneurs:
[Put an alligator on the shirt and make even more $$$$$]
London Dispersion Forces

The temporary separations
of charge that lead to the
London force attractions are
what attract one nonpolar
molecule to its neighbors.
Boiling points of simple

hydrocarbons in degrees Kelvin
400
C8H18
350
Temperature (Kelvin)
London forces increase with

the size of the molecules.
Fritz London
1900-1954
300
C5H12
C4H10
250
C3H8
200
C2H6
150
100
CH4
50
50
100
Molecular Weight
150
London Forces in Hydrocarbons

400
Boiling points of simple

hydrocarbons in degrees Kelvin
C8H18
350
C5H12
300
C4H10
250
C3H8
200
150
100
Simple hydrocarbons have

only London dispersion
forces as intermolecular
forces
C2H6
CH4
50
50
100
Molecular Weight
150
H
CH4
H
molecular
formula
structural
formula
109.5o
molecular
shape
H
C
H
H
tetrahedral
shape of
methane
tetrahedron
ball-and-stick
model
Methane is Tetrahedral
H
Methane is Tetrahedral
Methane
molecular
formula
structural
formula
molecular
shape
H
CH4
H
H
ball-and-stick
model
C
H
109.5o
Methane
H
C
H
H
tetrahedron
tetrahedral
shape of
methane
ball-and-stick
model of methane
Timberlake, Chemistry 7th Edition, page 365
Lewis structure of Ethane
Space filling model of Ethane
Ball and Stick model of Ethane
Structure of Propane
Structure of Butane
Ball and Stick Models
Ethane
C2H6
Propane
C3H8
First Ten Hydrocarbons

Name
Number of
Carbon Atoms
Molecular
Formula
Methane
CH4
CH4
Ethane
C2H6
CH3CH3
Propane
C3H8
CH3CH2CH3
Butane
C4H10
CH3CH2CH2CH3
Pentane
C5H12
CH3CH2CH2CH2CH3
Hexane
C6H14
CH3CH2CH2CH2CH2CH3
Heptane
CH3CH2CH2CH2CH2CH2CH3
Octane
C7H16
Nonane
C8H18
CH3CH2CH2CH2CH2CH2CH2CH3
C9H20
CH3CH2CH2CH2CH2CH2CH2CH2CH3
C10H22
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
Decane
10
Condensed Structural
Formula
Hydrocarbons
(alkanes)
First Ten Hydrocarbons

Number of
Carbon Atoms
Molecular
Formula
Boiling
Point, oC
# of
Isomers
Methane
CH4
-182.5
-161.5
Ethane
C2H6
-183.2
-88.6
n-Propane
C3H8
-187.7
-42.1
n-Butane
C4H10
-138.3
-0.5
n-Pentane
-129.7
36.1
n-Hexane
- 95.3
68.7
n-Heptane
- 90.6
98.4
n-Octane
- 56.8
125.7
18
n-Nonane
- 53.6
150.8
35
- 29.7
174.0
75
Name
n-Decane
10
C5H12
C6H14
C7H16
C8H18
C9H20
C10H22
Melting
Point, oC
Increasing mass and boiling point
Methane
16 g/mol
-161.5oC
Ethane
30 g/mol
-88.6oC
Propane
44 g/mol
-42.1oC
n-Butane
58 g/mol
-0.5oC
Hydrocarbons
Number of
Carbon Atoms
Alkanes
CnH2n + 2
Alkenes
CnH2n
Alkynes
CnH2n-2
CH4
Methane
____
_______
____
_______
C2H6
Ethane
C2H4
Ethene
C2H2
Ethyne
C3H8
Propane
C3H6
Propene
C3H4
Propyne
C4H10
Butane
C4H8
Butene
C4H6
Butyne
C5H12
Pentane
C5H10
Pentene
C5H8
Pentyne
6
7
8
9
10
C6H14
C7H16
C8H18
C9H20
C10H22
Hexane
Heptane
Octane
Nonane
Decane
C6H12
C7H14
C8H16
C9H18
C10H20
Hexene
Heptene
Octene
Nonene
Decene
C6H10
C7H12
C8H14
C9H16
C10H18
Hexyne
Heptyne
Octyne
Nonyne
Decyne
Isomers
The fat dog shook himself, and then rolled over on the wet rug.
The dog shook the fat rug, then rolled over and wet on himself.
(These two statements use the same words...

but have very different meanings.)
H
H C H
H H H H
H
H H H H
Methane
CH4
Butane
C4H10
H
?
R
C H
H
Methyl
-CH3
C C C C H
H H H H
R
C C C C H
H H H H
Butyl
-C4H9
Naming Alkanes
1. Find the longest continuous chain of carbon atoms in the molecule
2. Start numbering the chain at the carbon nearer the first branching point
(the substituents should have the lowest numbers possible)
3. Name and number the substituents
If there are two substituents attached to the same carbon,
assign both of them the same number
4. Write out the name of the molecule

List the substitutents names in alphabetical order
if there are two identical substituents on the molecule, use the prefix di;
if there are three identical substituents, use the prefix tri-;
if there are four identical substituents, use the prefix tetra(alphabetize the substituents by the main name of the substituent,
not by any prefixes the substituents may have)
Separate the substituents names with hyphens
Tag the name of the parent chain onto the end of the substituent names
A Few Extra Rules to Follow

Use commas to separate numbers
Use hyphens to separate numbers from the substituent names
Never name alkanes after drinking
Dont allow children to name alkanes unattended
Butane
Butane: C4H10
H H H
H-C-C-C-C-H
H H H
Butane Gas
lighters
Structural Isomers of C4H10
butane
H H H H
H
C C C C H
H H H H
C4H10
Isomers of
Butane
H HH
H C H
H
methyl propane or isobutane

Timberlake, Chemistry 7 Edition, page 383
th
C C C
H H H
IUPAC name
but-1-ene
cis-but-2-ene
trans-but-2-ene
2-methylpropene
C4H8
Isomers of Pentane
C5H12
These are called structural isomers.

H H H H
H
C C C C H
Butane
C4H10
C C C H
H H
Butene
Butane
C44H88
H
2-butene
n-butene
H H H
2
1-butene
H
1
C C C C H
H
H H H H
H H H
but(1)ene
H H CH3
H
C C C
1
6
52
43
CH3
CH3
H H C H
3
4
C C C C C C
H C H
25
CH3
H C H
16
H
3, 3 dimethyl hexane
or
Lowest sum of numbers

is correct
4, 4 dimethyl hexane
H
H
H
H
C
CH3H
CH3C
CHCH
CHCH
C
C 2C
C 3H
H
H
H
H
CH
C
H
3
H
C7H16
2, 4-dimethyl pentane
H
molecular formula
H H H
condensed
structural
formula
H H H H
H C C C C C C C H
H H H H H H H
Heptane
shorthand
H H H
H H H H
H C H
H C C C C C C C H
H H H H H H H
H H
H C C C
Br
H
H
C C
Cl
H
H
Cl
H
H
H
C C
H H
C
H
C C
H
H
H H H
H C C C C H
H H
H C H
H
butane
2 - methylbutane
H
H
H
C C
H H
C
C C
H
1, 4 - pentadiene
H
H
H
H C C C H
Cl
3 - chloro 1 - propyne
H H
H C C C
Br
Cl
Cl
3 - bromo, 1,1 -dichloro 1 - propene
Recall: double bond is lowest number

must put substituents in alphabetical order
Naming Branched Alkanes (IUPAC)

Octane
4-ethyl
6
2
4
4-ethyl-3,5-dimethyloctane
1
3-methyl and 5-methyl = 3,5-dimethyl
1. Root name: name of longest continuous C chain (parent chain)

Two equally long? Choose the one with more branches
2. Number C atoms in chain, starting at end with first branch

3. Identify substituents, give each a number (C it is connected to)
Two or more identical substituents: use prefixes (di-, tri-, tetra-, etc.)
4. List substituents alphabetically before root name

Do not alphabetize prefixes
5. Punctuation:
commas separate numbers from each other

hyphens separate numbers from names
no space between last substituent & root name
Structural Isomers: Pentane (C5H12)

pentane
2-methylbutane
2,2-dimethylpropane
Structural Isomers: Hexane (C6H14)

hexane
2,3-dimethylbutane
2-methylpentane
2,2-dimethylbutane
3-methylpentane
Structural Isomers: Heptane (C7H16)

heptane
2,2-dimethylpentane
2-methylhexane
2,3-dimethylpentane
3-methylhexane
Structural Isomers: Heptane C7H16
2,4-dimethylpentane
3-ethylpentane
3,3-dimethylpentane
2,2,3-trimethylbutane
Comparing Structural Isomers

C5H12
Structure
(Same formula, different structure)

Name
Boiling point (C)
pentane
36.0
2-methylbutane
27.9
2,2-dimethylpropane
9.5
More branching weaker London dispersion forces

BP/MP of Linear alkanes > BP/MP of branched alkanes
Naming Alkanes Problem Set

1.
2.
2-methylbutane
2-methylbutane
4.
3.
2,3-dimethylbutane
3,3,4-trimethylhexane

5. 3-ethyl-2,4,5-trimethylheptane
6. 6-ethyl-2,7-dimethylnonane

7.
8.
9.
4-ethyl-3-methylheptane
10.
5-tert-butyl-4-isopropyl-3methyloctane

11.
2,2,3-trimethylheptane
12. 6-ethyl-2-methyl-5-propylnonane

13.
14.
3,5-dimethyl-4-propylheptane
15.
3-ethyl-2,2,3trimethylpentane
3,4,4-trimethylheptane
16.
4-ethyl-6-isobutyl-2,9dimethyldecane

17. 1,1,6-trimethylhexane
4
2
18.
2-methyloctane
2-tert-butyl-4-ethyl-3-isopropylpentane
1
6
2
3
4-isopropyl-2,2,3,5-tetramethylheptane

1-sec-butyl-4-isobutyl-3-methylbutane
19.
4
5
10
2,5,8-trimethyldecane
20.
4
1
3
5
H
H C H
3,4-dimethyl octane
H C H
H H H
H H
H C C C C C
H H H H
H C H
H
H
C C H
H H
Cl Cl
H3C C C C CH2 CH3
H
CH3
3, 4 - dichloro 4 - methyl 2 - hexene
Functional Groups
Hydrocarbons in which some hydrogen atoms have been
replaced can be compared to an electric drill with attachments.
Inferring: What determines the function of the drill,
the drill itself or the attachments?
Electric drill
Forstner
drill bit
hole saw bit
Twist
drill bit
Philips
screwdriver bit
drum
sander
Alcohols (R-OH)
Methanol
(methyl alcohol)
Ethanol
R = -CH3
methyl
R = -CH2CH3 ethyl
(ethyl alcohol)
Primary, Secondary, Tertiary

Alcohols
Primary (1o)
Alcohol
Carbon attached
to OH group
H
R1
Alkyl
group
Secondary (2o)
Alcohol
OH
R1
Tertiary (3o)
Alcohol
R2
C
R2
OH
R1
R3
CH3
CH3
OH
Examples:
H
CH3
OH
CH3
OH
CH3
CH3
1o
2o
3o
(One alkyl group)
(Two alkyl groups)
OH
(Three alkyl groups)
Aldehydes and
Ketones
O
Aldehyde
O
Ketone
Acetaldehyde
ethanal, ethyl aldehyde
O
(CH3CH)
Formaldehyde
methanal
(CH2O)
R-C-H
R-C-R'
Acetone
dimethyl ketone, 2-propanone
(CH3COCH3)
Dimethyl Ether
Dimethyl ether
C2H6O
Flammable
anesthesia
R- Functional Groups
-CH3
methyl
-CH2CH3
ethyl
-CH2CH2CH2CH3
H
CH3CHCH2CH3
-CH2CH2CH3
propyl
CH3CCH3
isopropyl
sec-butyl
H
CH2 C CH3
butyl
isobutyl
CH3
CH3
C CH3
CH3
tert-butyl
Ball
Space
and filling
stick model
model of
of Ethylene
Ethylene
Alkenes and Alkynes

Alkene
Double bonds
ethene
Alkynes
A ball-and-stick model of ethene C2H4,

the simplest alkene.
Triple bonds
ethyne (acetylene)
A ball-and-stick model of acetylene
(IUPAC name ethyne)
Saturated vs. Unsaturated

Hydrocarbons
Saturated
Single bonds
Example:
Unsaturated
Double & triple bonds
Example:
Aliphatic Hydrocarbons
Alkane
General
formula
Typical
structural
formula
Carbon-carbon
bond type
Naming
suffix
Alkene
Alkyne
CnH2n - 2
Alkadiene
CnH2n + 2
CnH2n
CnH2n - 2
CCCC
C=CCC
C =CCC
C=CC=C
butane
1-butene
1-butyne
1,3-butadiene
all single bonds
one double bond
one triple bond
two double bonds
-ane
-ene
-yne
-diene
Hydrogenation
(an addition reaction)
tub (soft)
margarine
+ H2
vegetable oils
unsaturated
shortening
saturated
stick margarine
Cycloalkanes
Formula
CnH2n
Formula
H2
C
H2C CH2
Geometric
Formula
Name
Cyclopropane
H2
H2C C
C CH2
H2
H2C
H2
C
CH2
C C
H2 H2
H2C
H2C
Cyclobutane
H2
C
C
H2
Cyclopentane
CH2
CH2
Cyclohexane
Cycloalkanes
Formula
CnH2n
Formula
Geometric
Formula
Name
Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Benzene
An Aromatic Compound
C6H6
Resonance structures
Kekules dream
Benzene
Resonance in Benzene
Kelter, Carr, Scott, Chemistry A World d of Choices 1999, page 212
Shorthand notation of
Benzene
Structure of Benzene
H
H
C
C
C H
H C
C
H
C
H
H
H
C
C
C H
H C
C
H
C
H
H
H
C
C
C H
H C
C
H
C
H
Benzene
3-D
VSEPR Diagram
Cl
Names of
monosubstituted
benzene rings
Chlorobenzene
CH3
Toluene
Br
OH
Bromobenzene
Phenol
NO2
Nitrobenzene
CH=CH2
Styrene
Benzene
Mark Wirtz, Edward Ehrat, David L. Cedeno*
NO3-
Nitrobenzene
Aromatic Hydrocarbons
Cholesterol Compounds
CH3
6
C ortho
C
para
meta
position number name
1, 2
ortho- (o-)
1,3
meta- (m-)
1,4
para- (p-)
CH3
H
6
C CH3
H C
C
H
ortho-dimethylbenzene
or
1, 2 - dimethylbenzene
CH3
H
6
C H
H C
C
H
CH3
meta-dimethylbenzene
or
CH3
H
6
C H
H C
CH3
para-dimethylbenzene
or
MD
H
6
C H
H C
MD
para-docs
or
paradox
MD
H
6
C MD
H C
C
H
H
ortho-docs
or
orthodox
Fe2+
Fe2+
6
Fe2+ C
Fe2+
Fe2+
ferrous wheel
or
ferris wheel
Fe2+
NO2
H
C
C
C NO2
H C
C
H
C
H
o - dinitrobenzene
or
1, 2 - dinitrobenzene
NO2
CH3
C
C
C H
O2N C
C
H
C
NO2
2,4,6 - trinitrotoluene
or
TNT
CH3
CH3
Cl
C
C
Toluene
C Cl
H C
C
Cl
C
H
2, 4, 6 -trichloromethylbenzene
or
2, 4, 6 - trichlorotoluene
O
O C CH3
H
C
C
C COOH
H C
C
H
C
H
2-acetyloxybenzoic acid
or
(acetylsalicylic acid or aspirin)
H
C
C
H
H
C C
Cl C
CClCl
Cl C
3
C
C
Cl
H
H
dichlorodiphenyltrichloroethane
or
DDT
C
C
C
H
Cl
CH CH2
H
C
C
C H
H C
C
H
C
H
phenyl ethene
or
poly styrene aka
(styrofoam)
Carboxylic
Acids
COOH
O
R
- COOH
C OH
COOH
CH3CHCH2CH2COOH
Br
4-Bromopentanoic acid
Benzoic acid
NO2
p-Nitrobenzoic acid
CH2CH2COOH
Cl
3-Chloropropanoic acid
Classes of Organic Compounds

Class of
Compound
halocarbon
Functional
Group
F, Cl, Br,
I
alcohol
aldehyde
ketone
ester
amine
amide
R X
R OH
OH
ether
carboxylic acid
General
Formula
R O R
R C
R C
O
C
O
OH
OH
O
C
NH2
O
C NH2
R C
OR
R NH2
O
R C NH2
Example
CH3Cl
chloromethane
CH3CH2CH2OH
1-propanol
CH3OCH2CH3
methoxyethane
O
CH3CH2CH
propanal
O
CH3CCH3
propanone
O
CH3CH2COH
propanoic acid
O
CH3COCH3
methylethanoate
CH3CH2CH2NH2
propanamine
O
CH3CH2CNH2
propanamide
Organic Nomenclature Flow Chart
Functional
Groups
Functional
Groups
Order of Priority of Functional Groups

Order of
priority
Functional group
Formula
Carboxylic acid
Functional group
Formula
Ketone
-CO
Sulfonic acid -SO3H
Alcohol
-OH
Ester
10
Phenol
-OH
Acid chloride -COCl
11
Thiol
Amide
-CONH2
12
Amine
-NH2
Nitrile
-CN
13
Ether
-OR
Aldehyde
-CHO
14
Sulfide
-SR
Selinger, Chemistry in the Marketplace, 1994, page 23
-COOH
Order of
priority
-COOR
-SH
Esters
O
R C O R
H H O
H
C C C O H
CH3
from propanoic acid

methyl group
H H
an
ester
a carboxylic
acid
propanoic acid
An ester is similar to a carboxylic acid,

but the acidic hydrogen has been
replaced by an alkyl group
methyl propanoate
Naming Esters
O
R C O R
Name the following ester:
O
CH3CH2CH2COCH2CH3
Step 1) the ester alkyl group (R) = ethyl

Step 2) the acid (R) = butanoic acid
Step 3) the name = ethyl butanoate
Ester L
Ester L
ab I
ab I
Formation of an Ester
H H H O
H
C C C C O
OH
H +
Ester La
Ester La
b II
b II
H H
HO C C H
H H H
butyric acid (butanoic acid)
H H
ethyl alcohol
+
water
ethyl butyrate (tastes and smells like pineapple)
Ketone
H O H
H H
H C C C C C H
1
O
R C R'
H H H
2-pentanone
C5H10O
Ester
H H O
H C C C O C H
2
H H
3 carbons = propane
O
R C O R'
H
R'
methyl propanoate
1) Name the R' first (R' = methyl)
2) Find carbon chain and include the
carbonyl carbon.
3) Drop the ending and add -yl
C4H8O2
CH3
Ester
H C O C CH3
Raspberry
R C O R'
H O
CH3
H C C O CH2 CH2 C CH3

H
CH3
Banana
H O
H C C O CH2 (CH2)6 CH3
H
PP
PP
Ester
Ester
Lab
Lab
Orange
Ester
H O
H C C O CH2 CH2 CH3
H
Pear
O
R C O R'
H
H
C
H O
H C C O CH2 C
H
Peach
C H
C
H
C
H
Carboxylic acid
H
R C
H C H
H
H C
H H
H
C
C C
O
OH
3-methylpentanoic acid
C6H12O2
O
OH
Ether
R O R'
H H
H H H H
H C C O C C C C H
H H
H H H H
ethyl butyl ether (common name)
or
ethoxybutane (IUPAC)
C6H14O
3-ethyl-3-hexanol
Alcohol
R OH
H C H
H C H
H H
H H
H C C C C C
H H
H H
H
C H
H
C8H18O
OH
Carboxylic acid
R C
H
H
C C
H
O
OH
ethanoic acid
C2H4O2
O
OH
Alcohol
H H
R OH
HO C C C OH
H H H
1,3-propanediol
C3H8O2
Draw structural formulas for the following:
a.
3-heptene
b.
trichloromethane
c.
2-chloro-3-phenylhexane
d.
1,3-cyclopentadiene
e.
toluene (methylbenzene)
f.
1,4-dibromobenzene
g.
2-bromo-3-methyl-2-butene
Write the condensed formulas for the following haloalkanes:
a.
ethyl chloride (common name) or chloroethane (IUPAC)
b.
bromomethane
c.
1-bromo-3-chlorocyclopentane
d.
1,1-dichlorocyclohexane
e.
2,2,3-trichlorobutane
f.
2,4-dibromo-2,4-dichloropentane
Write a correct IUPAC (or common name) for the following:

a.
CH3CH2Br
b.
Cl Cl
bromoethane (ethyl bromide)

2,3-dichlorobutane
Cl
CH3CHCHCH3
c.
chlorocyclopentane
Cl
d.
e.
Br
CH3CH2CHCH2CHCH3
2-bromo-4-chlorohexane
Cl
F
1-chloro-1-fluorocyclobutane
Draw structures for the following:
1,1,1-trifluoroethane
cis-2-butene
1-heptyne
2-chloro-4,5-diethylnonane
cyclohexane
ethylcyclopropane
meta-dichlorobenzene
2,4,6-trinitrotoluene
ortho-iodotoluene
ethyl pentanoate
2-bromohexanal
methyl propanamide
propoxypropane (propylpentyl ether)
m-iodophenol
1,3-propanedioic acid
propylamine
1,4-butandiol
3-chloropentanoic acid
1,3-dibromo-2-propanone
methyl-3-chloropropyl ether
3-hydroxy-1-pentyne
F
F
C C H
F
1,1,1-trifluoroethane
C2H3F3
H
C C
H3C
CH3
cis-2-butene
H3C
H
H
C C
CH3
trans-2-butene
C4H8
H H
H H H H
H C C C C C C C H
H H H H H H
1-heptyne
C7H12
H H H
H H H H
H C H
H C C C C C C C H
H H H H H H H
H H
H C C C
Br
H
H
C C
Cl
H
H
Cl
H
H
H
C C
H H
C
H
C C
H
H
Chirality: Chiral vs. Achiral
right shoe
left mitt
right-handed
scissors
Chiral
glass
plate
Achiral
tennis
racket
Chirality
H
mirror
Cl
Cl
Br
Br
Cl
I
Br
Cl
Br
I
cis and trans isomers

Geometric Isomers
H
H3C
H
C=C
CH3
H3C
C=C
H
cis-2-butene
(same side)
trans-2-butene
(opposite side)
CH3
H
Geometric Isomers
Isomerism
trans
cis
Stereoisomers
(Structural Isomers)
mirror images
Other Functional Groups to Recognize

Ethers
Amines
Amides
(EETH erz) (uh MEENZ) (uh MIDZ or AM idz)
N
coca-ine
Tatoo-ine
caffe-ine
O
CN
Organic Reactions
combustion of hydrocarbons OR compounds w/only
C, H, and O: products areCO2 and H2O
Write the equation for the
complete
combustion of 2-methyl-2pentene.
C6H12 + 9 O2 6 CO2 + 6 H2O
Write the equation for the complete
combustion of ethylbutanoate.
C6H12O2 + 8 O2 6 CO2 + 6 H2O
substitution: an H atom is removed and something

else is put in its place
halogen atom replaces an H.
-- In halogenation, a _______
Write an equation for the
reaction
between ethane and chlorine.
H H
H H
H CCH + Cl2 H CCCl + HCl
H H
H H
If more chlorine is provided,
the reaction will produce...
H H
H H
H CCCl + Cl2 ClCCCl + HCl
H H
H H
AND SO ON.
Substitution occurs with aromatic compounds, too.

Br
+ Br2
+ CH3CH2Cl
catalyst
catalyst
+ HBr
+ HCl
Ethylbenzene is an important
intermediate in the production
of styrene which, in turn, is
used to make polystyrene.
Roughly 25 million tons of
ethylbenzene are produced and used every year.
addition: a multiple bond is broken and

two things are inserted
H H
H
H
BrCCBr
+ Br2
C=C
H
H
H H
H H
H
H
H CCBr
+ HBr
C=C
H
H
H H
H H
H
H
H2SO4
H CCOH
+ H2O
C=C
H
H
H H
H
H
H Cl
H
HCCCCH + Cl2
H CC=CC H
H
Cl H
H
H
A specific addition rxn is hydrogenation, in which

__
H is added across a multiple C-C bond.
-- requires a catalyst (usually a finely-divided
_____)
metal to rupture the multiple bond
H
H
C=C
H
H
+ H2
catalyst
H H
HCCH
H H
Another addition reaction is polymerization.

H
H
H H H H
C=C
H
H
H
H
CCCC
C=C
H
HH
H
H H H H
C=C
H
H lots of ethylene
polyethylene
condensation
(or elimination,
or dehydration):
water is a product
_____
-- One reactant provides an __,
H
the other provides an ___.
OH
Complex protein
molecules are
made from
condensation
reactions of
amino acids.
NO2
+ HNO3
H2SO4
CH3CH2OH + CH3OH
alcohol mc alcohol mc
+ H2O
CH3CH2OCH3 + H2O
an ether
water
-- Amides can be formed in condensation rxns

between carboxylic acids and amines.
Write the equation for the reaction between
butanoic acid and nitrogen trihydride.
Ammonia is the simplest amine.
O
O
+ NH3
+ H2O
NH2
OH
carboxylic acid amine
amide
water
Esterification is a condensation reaction between a

carboxylic acid and an alcohol.
butanoic acid and 1-butanol.
O
+
OH
HO
O
O
butylbutanoate
+ H2O
(the active substance in
the characteristic
flavor/odor of pineapple)

3-phenyl-2-propenoic acid and ethanol.
O
+ HO
OH
O
+ H2O
O
ethyl-3-phenyl-2-propenoate
(i.e, ethyl cinnamate )
(the active substance in

the characteristic
flavor/odor of cinnamon)
When in doubt,
make water.
Mr. B
Amino Acid
NH21- NH3
NH41+
Amine
Ammonium ion
Ammonia
Polymers
monomer
Jaffe, New World of Chemistry, 1955, page 603
homo
chain polymer
monomer
copolymer
Copyright 2007 Pearson Benjamin Cummings. All rights reserved.
Polymerization
Polymers = Monomer + Monomer +
Synthetic Polymers
Nylon
plastics
Vulcanized rubber
polyethylene
Natural Polymers
Silk
Proteins (amino acids)
Starch (sugars)
Polymers
H2C = CH2
CH2 CH2 CH2 CH2
Ethene (ethylene)
Polyethylene
Cl
H2C = CH
Chloroethene
(vinyl chloride)
Cl
Plastic bottles, film,

insulation material
Cl
CH2 CH CH2 CH
Polyvinyl chloride (PVC)
Plastic pipes and

tubing, garden
hoses, garbage bags
Polymers
CH3
CH3CH = CH2
Propene (propylene)
FC=CF
Tetrafluoroethene
CH3
CH2 CH CH2 CH
Ski and hiking

clothing, carpets,
artificial joints
Polypropylene
CCCC
F
Teflon
Nonstick coatings
Polymers
Cl
H2C = C Cl
1,1 Dichloroethene
H2C = CH
Phenylethene
Cl
Cl
CH2 C CH2 C
Cl
Plastic film
and wrap
Cl
Saran
CH2 CH CH2 CH
Polystyrene
Plastic coffee
cups and cartons,
insulation
Slime
PVA
+ PVA + PVA
With cross-linking agent

(borax solution)
What are some things you think of

when I say organic?
Medicine
Plastics
Soil
Soap
Petroleum
Grass
Clothing
PRISM fellow: Mr. Kevin J. Hodel
Organic - the study of carbon containing

compounds that their properties
Why carbon??
Strong bonds
between carbons
Low reactivity of
carbon compounds
Geometry of carbon
compounds
Diamonds
Graphite
Polymers
Polymer - a large organic molecule
composed of smaller units bonded together

These smaller units are called monomers.
Tires
Vulcanized rubber was discovered by

mistake!!
soft and weak until heated then forms disulfide

linkages between the rubber polymers.
Natural Polymers
Rubber
Cotton
Paper
Cotton and paper are made of cellulose

which is the most abundant natural polymer
in the world.
Starch
Potatoes, corn, bread
Synthetic Polymers
Half of the industrial chemists work in

some area of polymer chemistry.
In 1996, more than 270 lbs of plastic
was produced per person in the US.
Types of Synthetic Polymers
Elastomers - can be highly stretched

and returns to their original shape.
Fibers - polymers that exhibit little or no

elasticity (threadlike)
Plastics - synthetic polymers that are

more elastic than fibers but less elastic
the elastomers.
Common Polymers
Polystyrene foam can be made into cartons to protect eggs or into
packing peanuts to cushion fragile objects for shipping.
CH2 CH CH2 CH
Plastic coffee
cups and cartons,
insulation
Polystyrene
Polyethylene: You probably see polyethylene every day! Its the

plastic used to make many containers, among other things.
CH2 CH2 CH2 CH2
Polyethylene
Plastic bottles, film,

insulation material
Water-resistant paints and varnishes derive from a family of

synthetic polymers called acrylics.
Recycling
Before: Milk jug.
After: Picnic table.
Before: Bread bag.
After: Trash can.
Before: Sandwich box.
After: Frisbee.
Plastic Resin Codes
Copyright 2007 Pearson Benjamin Cummings. All rights reserved.
Addition Reactions
H
C C
H
H
H H
+ HH
Ni
C C
H
H
C C
H H
H Br
+ Br Br
Ni
C C
Br H
Acid-Catalyzed Hydration
H
C C
H H
+ H OH
H2SO4
H OH
water
ethene
C C
ethanol
Write out the mechanism for the formation of isopropyl alcohol

(used as rubbing alcohol), from propene.
C C
H H
+ H OH
H
ethene
H2SO4
C C
OH H
water
ethanol
Molecular Geometry
180o
H
C
Trigonal planar
Linear
109.5o
109.5o
Tetrahedral
107.3
Trigonal pyramidal
104.5o
Bent
H2O CH4 AsCl3 AsF5
BeH2
BF3 CO2
Order of Priority of Functional Groups

Order of
priority
Functional group
Formula
Carboxylic acid
Functional group
Formula
Ketone
-CO
Sulfonic acid -SO3H
Alcohol
-OH
Ester
10
Phenol
-OH
Acid chloride -COCl
11
Thiol
Amide
-CONH2
12
Amine
-NH2
Nitrile
-CN
13
Ether
-OR
Aldehyde
-CHO
14
Sulfide
-SR
Selinger, Chemistry in the Marketplace, 1994, page 23
-COOH
Order of
priority
-COOR
-SH

E2 Organic Chemistry

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E2 Organic Chemistry

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Organic

Distilling Crude Oil

Alkenes & Alkynes

Made the first organic compound from

Distilling Crude Oil

Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 429

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 648

Petroleum / natural gas

Distilling Crude Oil

American Petroleum Usage

93% Energy Marketplace

At $3.00 per gallon

100 Nylon Shirts

London Dispersion Forces

Boiling points of simple

London forces increase with

London Forces in Hydrocarbons

Boiling points of simple

Simple hydrocarbons have

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 634

Lewis structure of Ethane

Space filling model of Ethane

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635

Ball and Stick model of Ethane

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635

Ball and Stick Models

Timberlake, Chemistry 7th Edition, page 366

First Ten Hydrocarbons

First Ten Hydrocarbons

Increasing mass and boiling point

(These two statements use the same words...

4. Write out the name of the molecule

A Few Extra Rules to Follow

Structural Isomers of C4H10

methyl propane or isobutane

These are called structural isomers.

Lowest sum of numbers

3 - bromo, 1,1 -dichloro 1 - propene

Recall: double bond is lowest number

Naming Branched Alkanes (IUPAC)

3-methyl and 5-methyl = 3,5-dimethyl

1. Root name: name of longest continuous C chain (parent chain)

2. Number C atoms in chain, starting at end with first branch

4. List substituents alphabetically before root name

commas separate numbers from each other

Structural Isomers: Pentane (C5H12)

Structural Isomers: Hexane (C6H14)

Structural Isomers: Heptane (C7H16)

Structural Isomers: Heptane C7H16

Comparing Structural Isomers

(Same formula, different structure)

Boiling point (C)

More branching weaker London dispersion forces

Naming Alkanes Problem Set

Naming Alkanes Problem Set

Naming Alkanes Problem Set

Naming Alkanes Problem Set

Naming Alkanes Problem Set

Naming Alkanes Problem Set

Naming Alkanes Problem Set

3, 4 - dichloro 4 - methyl 2 - hexene

hole saw bit

Primary, Secondary, Tertiary