Organic Chemistry
Chapter 24
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Common Elements in Organic Compounds
24.1
Classification of Hydrocarbons
24.1
Alkanes
Alkanes have the general formula CnH2n+2 where n = 1,2,3,…
• only single covalent bonds
• saturated hydrocarbons because they contain the
maximum number of hydrogen atoms that can bond with the
number of carbon atoms in the molecule
CH4
C2H6
C3H8
methane
ethane
propane
24.2
Structural isomers are molecules that have the same
molecular formula but different structures
24.2
How many structural isomers does pentane, C5H12, have?
H
H
H
H
H
H
C
C
C
C
C
H
H
H
H
H
H
H
CH3 H
C
C
H
CH3 H
n-pentane
H
H
H
CH3 H
H
C
C
C
C
H
H
H
H
2-methylbutane
H
C
H
2,2-dimethylpropane
24.2
Alkane Nomenclature
1. The parent name of the hydrocarbon is that given to the
longest continuous chain of carbon atoms in the molecule.
CH3
CH3
1
CH2
2
CH2
3
CH
4
CH2
5
2. An alkane less one hydrogen
atom is an alkyl group.
24.2
CH4
methane
CH3
methyl
CH2
6
CH3 4-methylheptane
7
Alkane Nomenclature
24.2
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
CH3
5
4-methylpentane
24.2
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
CH
2
C
3
CH2
4
CH2
5
CH3
6
CH3
3,3-dimethylhexane
24.2
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
Br
CH2
1
NO2
CH2
2
CH
3
CH3
4
1-bromo-3-nitrobutane
24.2
What is the IUPAC name of the following compound?
CH3
CH3
1
CH
C2H5
CH2
2
3
CH
4
CH2
5
CH2
6
CH2
7
CH3
8
2-methyl-4-ethyloctane
What is the structure of 2-propyl-4-methylhexane?
C2H5
CH3
1
CH
2
CH3
CH2
3
CH
4
CH2
5
CH3
6
24.2
Alkane Reactions
Combustion
CH4 (g) + 2O2 (g)
CO2 (g) + 2H2O (l) DH0 = -890.4 kJ
Halogenation
light
CH4 (g) + Cl2 (g)
CH3Cl (g) + HCl (g)
Cl2 + energy
Cl• + Cl•
H
H
Cl• + H
C
H
H
•C
H
H
H
C • + Cl
H
H + HCl
H
Cl
H
C
H
Cl + Cl•
24.2
achiral
chiral
24.2
Cycloalkanes
Alkanes whose carbon atoms are joined in rings are called
cycloalkanes. They have the general formula CnH2n where n =
3,4,…
24.2
Cycloalkanes
24.2
Alkenes
Alkenes have the general formula CnH2n where n = 2,3,…
• contain at least one carbon-carbon double bond
• also called olefins
CH
CH2
CH2
CH3
CH3
CH
1-butene
Cl
Cl
C
H
Cl
H
C
cis-dichloroethylene
CH3
2-butene
C
H
CH
H
C
Cl
trans-dichloroethylene
24.2
Cis-Trans Isomerization in the Vision Process
24.2
Alkene Reactions
Cracking
C2H6 (g)
Pt
catalyst
CH2
CH2 (g) + H2 (g)
Addition Reactions
CH2
CH2 (g) + HBr (g)
CH3
CH2
CH2 (g) + Br2 (g)
CH2Br
CH2Br (g)
CH2Br (g)
24.2
Alkynes
Alkynes have the general formula CnH2n-2 where n = 2,3,4,…
• contain at least one carbon-carbon triple bond
CH
C
CH2
1-butyne
CH3
CH3
C
C
CH3
2-butyne
Production of acetylene
CaC2 (s) + 2H2O (l)
C2H2 (g) + Ca(OH)2 (aq)
24.2
Alkyne Reactions
Hydrogenation
CH
CH (g) + H2 (g)
CH2
CH2 (g)
Addition Reactions
CH
CH (g) + HBr (g)
CH2
CH
CH (g) + Br2 (g)
CHBr
CH
CH (g) + 2Br2 (g)
CHBr2
CHBr (g)
CHBr (g)
CHBr2 (g)
24.2
Chemistry In Action: Ice That Burns
Aromatic Hydrocarbons
H
H
H
H
C
C
C
C
C
C
H
H
H
H
H
C
C
C
C
C
C
H
H
H
24.3
Aromatic Compound Nomenclature
ethylbenzene
CH2CH3
aminobenzene
NH2
Cl
chlorobenzene
6
2
5
3
4
nitrobenzene
Br
Br
1
NO2
Br
Br
1,2-dibromobenzene
1,3-dibromobenzene
24.3
Aromatic Compound Reactions
Substitution reaction
H
Br
H
H
+ Br2
H
H
H
FeBr3
catalyst
+ HBr
H
H
H
H
H
H
CH2CH3
H
H
+ CH3CH2Cl
H
H
H
H
H
AlCl3
catalyst
+ HCl
H
H
H
24.3
Polycyclic Aromatic Hydrocarbons
24.3
Functional Group Chemistry
Alcohols contain the hydroxyl functional group and have the
general formula R-OH.
24.4
Biological production of ethanol
C6H12O6 (aq)
enzyme
2CH3CH2OH (aq) + 2CO2 (g)
Commercial production of ethanol
CH2 CH2 (g) + H2O (g)
H2SO4
CH3CH2OH (g)
Metabolic oxidation of ethanol
CH3CH2OH
alcohol dehydrogenase
CH3CHO + H2
24.4
Functional Group Chemistry
Ethers have the general formula R-O-R’.
Condensation Reaction
CH3OH + HOCH3
H2SO4
catalyst
CH3OCH3 + H2O
24.4
Functional Group Chemistry
O
Aldehydes and ketones contain the carbonyl ( C
functional group.
O
)
• aldehydes have the general formula R C H
O
• ketones have the general formula R C R’
O
O
O
H C H
H C CH3
H3C C CH3
formaldehyde
acetaldehyde
acetone
24.4
Functional Group Chemistry
Carboxylic acids contain the carboxyl ( -COOH ) functional
group.
24.4
Functional Group Chemistry
Esters have the general formula R’COOR, where R is a
hydrocarbon group.
O
CH3COOH + HOCH2CH3
CH3 C O CH2CH3 + H2O
ethyl acetate
24.4
Functional Group Chemistry
Amines are organic bases with the general formula R3N.
CH3NH2 + H2O
CH3CH2NH2 + HCl
RNH3+ + OH-
CH3CH2NH3+Cl-
24.4
24.4
Chemistry In Action: The Petroleum Industry
Crude Oil