Chapter 22
Molecular  Shows type & number of
atoms in compound
Structural  Shows bonding pattern &
the shape of molecules
Methane
Ethane
CH4
C 2H 6
Molecular
H
Structural
H
C
H
Condensed
Structural
CH4
H
H
H
H
C
C
H
H
H
CH3CH3
The study of carbon & most carbon
compounds
Recall…
 Carbon has 4 valence electrons
 It can form 4 covalent bonds
 Makes carbon a versatile atom
Hydrocarbons  Compounds containing only C & H
 Simplest organic molecules
Common Elements in Organic Compounds
 Alkanes - saturated
 Alkenes - unsaturated
 Alkynes – unsaturated
 Saturated Molecules  Contain only single bonds
 Unsaturated Molecules  Contain one or more double or triple bonds
 Hydrocarbon with only single covalent bonds
 Saturated with H atoms
 Formula is CnH2n+2 where n = 1,2,3, etc.
 As # of C increases, boiling point increases
 Names end in –ane
 Ex. methane (CH4), ethane (C2H6), propane (C3H8)
Physical Properties of Some Alkanes
 A group of related compounds in which each member differs
from the previous compound by the same additional unit.
 Members have related structures and properties
 Ex. alkanes differ by groups of CH2
 Table P
 Prefix is based on the
number of carbon atoms in a
‘chain’
Alkanes
 Use Table P to determine the
prefix, based on the # of carbon
atoms in the compound
 End in -ane
Hexane
Alkane Nomenclature
1. The parent name of the hydrocarbon is that given to the
longest continuous chain of carbon atoms in the
molecule.
CH3
4-methylheptane
CH3
1
CH2
2
CH2
3
CH
4
CH2
5
2. An alkane less one hydrogen
atom is an alkyl group.
CH4
methane
CH3
methyl
CH2
6
CH3 heptane
7
Alkane Nomenclature
3. When one or more hydrogen atoms are replaced by other
groups, the name of the compound must indicate the
locations of carbon atoms where replacements are made.
Number in the direction that gives the smaller numbers for
the locations of the branches.
CH3
CH3
1
CH
2
CH2
3
CH2
4
CH3
5
CH3
2-methylpentane
CH3
1
CH2
2
CH2
3
CH
4
4-methylpentane
CH3
5
Alkane Nomenclature
4. Use prefixes di-, tri-, tetra-, when there is more than one
alkyl branch of the same kind.
CH3
1
CH3
CH3
CH
CH
2
3
CH2
CH2
4
CH3
5
6
2,3-dimethylhexane
CH3
CH3
1
CH2 C
2
3
CH2
4
CH2
5
CH3
3,3-dimethylhexane
CH3
6
Alkane Nomenclature
5. Use previous rules for other types of substituents.
CH3
1
Br
NO2
CH
CH
2
3
CH3
4
2-bromo-3-nitrobutane
Cl
CH2
1
F
CH2
2
CH
3
CH3
4
1-chloro-3-fluorobutane
What is the IUPAC name of the following compound?
CH3
C2H5
CH3
CH
CH2
CH
CH2
CH2
CH2
CH3
1
2
3
4
5
6
7
8
2-methyl-4-ethyloctane
Draw the structural formula of 2-propyl-4-methylhexane.
C3H7
CH3
CH3
CH
CH2
CH
CH2
CH3
1
2
3
4
5
6
Sample Exercise
Give the IUPAC name of the following compound:
Give the IUPAC name of the following compound:
2.
Name the following:
3,4-dimethylheptane
2,4-dimethylpentane
3. Draw the complete structural formulas for the
following compounds:
a. 3-ethylhexane
b. 2,2,4-trimethylpentane
1. Draw the structural formula of
5-ethyl-2,4,6-trimethyloctane.
4. Write the structural formulas for:
a. 3-ethyl-2-methylpentane
b. 2,3,-dimethylhexane
c. 4-ethyl-2,3,4-trimethyloctane
Hydrocarbon with at least one double covalent bond
Unsaturated with H atoms
Formula is CnH2n where n = 2,3, etc.
Names end in -ene
Ex. ethene (C2H4), propene (C3H6), butene (C4H8)
 Alkenes
 End in –ene
 Number the location of the double bond
CH2
CH
CH2
1-butene
CH3
CH3
CH
CH
2-butene
CH3
 Hydrocarbon with at least one triple covalent bond
 Unsaturated with H atoms
 Formula is CnH2n-2 where n = 2,3, etc.
 Names end in -yne
 Ex. ethyne (C2H2), propyne (C3H4), butyne (C4H6)
 Alkynes
 End in –yne
 Number the location of the triple bond
CH
C
CH2
1-butyne
CH3
CH3
C
C
2-butyne
CH3
 Compounds with the same molecular formula but different
structural formulas
 Ex. C4H10
 Isomers have different chemical & physical properties
 As the # of C atoms increase, the # of isomers increase
(Straight-chain form)
(branched-chain form)
Draw structural isomers for C5H12:
H
H
H
H
H
H
C
C
C
C
C
H
H
H
H
H
H
H
CH3
H
C
C
C
H
CH3
H
pentane
H
H
H
CH3
H
H
C
C
C
C
H
H
H
H
2-methylbutane
H
2,2-dimethylpropane
H
Chapter 23
 A specific arrangement of atoms in an organic
compound
 Capable of characteristic chemical reactions
 Aka the ‘chemically functional’ part of the
molecule
 Allows organic compounds to be classified
R=
carbon chain or rings
attached to functional
group
 Contain covalently bonded halogens:
 F, Cl, Br, or I
 Named by describing location of the halogen(s) attached to
the chain
H Cl Cl H
H—C—C—C—C—H
H Cl H
H
2,2,3–trichlorobutane
 Contain a hydroxyl group: –OH
 Alcohols are not electrolytes
Do not form ions/conduct electricity
 Hydroxyl groups are polar
Allows alcohols to be soluble in water
 To name:
change the ending -e to –ol
Sample Problems
Name the alcohol:
Example 1
H H H H
H—C—C—C—C—OH
H H H
Name: 1–butanol
CSF: CH3CH2CH2CH2OH
H
H H H
Example 2
H
H—C—C—C—C—H
H H OH H
Name: 2–butanol
CSF: CH3CH(OH)CH2CH3
H
H—C—H
Example 3
H H
H
H—C—C—C—C—H
H H OH H
Name: 2–methyl, 2-butanol
CSF: CH3C(OH)(CH3)CH2CH3
H H H
Example 4
H
H—C—C—C—C—OH
H H OH H
Name: 1,2–butanediol
CSF: CH3CH2CH(OH)CH2OH
H H OH H
Example 5
H—C—C—C—C—OH
H H OH H
Name: 1,2,2–butanetriol
CSF: CH3CH2C(OH)(OH)CH2OH
Example 6
Draw and then name the following alcohol:
CH3CH2CH2CH2CH2OH
O
• aldehydes have the general formula
propanal
R C H
 Contain a carbonyl group: -C=O
 C is attached to at least one H at
end of the molecule
 Carbonyl groups are polar!!!
 To name: change the
-e ending to -al
O
• ketones have the general formula R C R′
 Contain a carbonyl group: -C=O
 C is joined to two other C’s in the
middle of the molecule
 To name: change the -e
ending to -one
Are compounds in which oxygen is
bonded to two carbon groups
The groups attached to the ether linkage
are names in alphabetical order and is
followed by the word ether
H
H
H–C–O–C–H
H
H
dimethyl ether
H
H H
H–C–O–C–C–H
H
H H
H H
H H
H–C–C–O–C–C–H
H H
H H
ethyl methyl ether diethyl ether
Functional Group Chemistry
Ethers have the general formula R−O−R′.
Condensation Reaction
CH3OH + HOCH3
H2SO4
catalyst
CH3OCH3 + H2O
propanoic acid
 Contains a carboxyl group: -COOH
 Usually weak electrolytes
 To name: change the -e
ending to -oic acid
 Derivatives of a carboxylic acid & an
alcohol
 R-CO-OR’
 To name:
change -e ending
to -oate
 Formed when 1 or more H atoms in ammonia (NH3) are
replaced with an alkyl group
 To name: change the -e ending to -amine &
number the alkane chain to show where the
amine group is located
H
H
N
H
CH3
N
H
ammonia
H
CH3
N
H
methyl amine
CH3 CH3
N
CH3
CH3
dimethyl amine trimethyl amine
 A carboxyl group:
-COOH
 An amine group: -NH2
 H atom
 R group attach to a central
carbon atom
H atom in an amine group
reacts with a –OH group of an
organic acid
Occurs when two amino acids
form a peptide bond
change the -e ending to -amide
 To name:
O
O
CH3—C—NH2
C3H7—C—NH2
ethanamide
butanamide

Identify the functional group in each structure:
1. CH3 – OH
2. CH3 – CH2 – NH2
3. CH3 – CH2 – CH2 – Br
4. CH3 – CH2 – O – CH2 – CH3
Burning a hydrocarbon in oxygen to produce water and
carbon dioxide
If O2 supply is limited CO may be produced instead of
CO2
Complete combustion
C3H8(g) + 5O2(g) —> 3CO2(g) + 4H2O(g)
Incomplete combustion
2C3H8(g) + 7O2 —> 6CO(g) + 8H2O(g)
 Replacement of one or more of the H atoms in a saturated
hydrocarbon with another atom or group
 Ex. halogenation or hydrogenation
CH4 + Cl2  CH3Cl + HCl
C2H6 + Cl2  C2H5Cl + HCl
CH3I + KOH  CH3OH + KI
 The addition of one or more atoms to a double or triple bond
H2C CH2 + Br2
CH3CH CHCH3 + HBr
H2C CH2
Br Br
CH3HC CHCH3
H
Br-
 Reaction between an organic acid and an alcohol to produce an ester plus water
H3C
O
C
+ HO CH2CH3
OH
H3C
O
C
+ H2O
OCH2CH3
Reaction between an ester and an inorganic base to
produce an alcohol and a soap
Ex. Fat + NaOH  soap + glycerol
In the soap–making process, an animal fat or
vegetable oil is boiled with a strong base, NaOH
Fat
+
Alkali
→ Glycerol + Soap

C6H12O6  2C2H5OH + 2CO2
 Reaction where yeast cells break
down glucose into CO2 and ethanol
 Reaction where many monomers covalently bond to form a
polymer
 Polymer –
 organic compounds made up of chains of smaller units
covalently bonded together
 Ex. proteins, starches, DNA
Addition Polymerization Reaction that joins monomers of unsaturated
compounds
nC2H2 —> (C2H2)n
H H
HH
H H
C=C + C=C + C=C
H H
HH
H H
HH HH HH
– C-C––C-C––C-C –
HH HH HH
Condensation Polymerization Reaction where monomers are joined together and a
water molecule is released
Monomers form an ether or ester linkage
Chemistry In Action: The Petroleum Industry
Crude Oil
Fractions Obtained from Crude Oil