Ch.

22
Hydrocarbons
Organic Chemistry
• The study of carbon containing compounds
• C bonded to H, N, O, S, P and halogens (17th column)

• Hydrocarbon: simplest organic compound that contains only H and C

**because C has four valence electrons, a carbon atoms always forms four
covalent bonds
Organic vs. Inorganic

Organic Inorganic
Made of nonmetals (metalloids) Made of metal & nonmetal
Covalent bonds Ionic bonds
Most insoluble in water Most soluble in water
Most soluble in organic solvent Most non-soluble in organic
solvents
Low MP & BP High MP & BP
Alkanes
• Alkane
• Hydrocarbon with ALL single bonds
• General formula CnH2n+2
• Suffix – ane

C Atoms H Atoms Formula

3 2(3) + 2 = 8 C3H8
6 2(6) + 2 = 14 C6H14
Naming Alkanes
• A prefix is used to tell the number of C atoms
Prefix # of C Atoms
Meth – 1
Eth- 2
Prop - 3
But - 4
Pent - 5
Hex - 6
Hept - 7
Oct - 8
Non - 9
Dec - 10
Structural Formula
• Shows the arrangement of atoms
• Expanded: all the individual bonds are drawn

• Condensed: each carbon is written with the H atoms connected to it

• CH3CH2CH3 or CH3 – CH2 – CH3

• Line bond: shows the C-C bonds as lines

2 C-C bonds
Practice:
1. Draw an expanded formula for butane

2. Draw the condensed formula for hexane

3. Draw a line formula for pentane

4. Name: CH3(CH2)6CH3
Practice:
1. Draw an expanded formula for butane

2. Draw the condensed formula for hexane

CH3CH2CH2CH2CH2CH3

3. Draw a line formula for pentane

4. Name: CH3(CH2)6CH3
Octane
 Branched – Chain Alkanes
• A side group called a branch or a substituent is attached to a
carbon chain

• Also known as a alkyl group

• Composed of one or more carbon atoms attached to the carbon
chain
• Derived from the corresponding alkane by removing one hydrogen
• Named by replacing the –ane ending of the corresponding alkane
with - yl
Naming Branched – Chain Alkanes
1. The longest chain is named as the main chain
2. Any carbon branches use their alkyl names
3. Number the branches by counting the main chain from the end
nearest the first side group
4. Branches are listed in alphabetical order with the number where
they are attached (ignore prefixes like di- & tri- when alphabetizing)
5. If a tie, go with the lowest set of numbers
9 8 7 6 5 4 3
CH3CH2CH2CHCH2CH2CHCH3 6-ethyl-3-methyl nonane
2 1
CH2CH3 CH2CH3
 Practice:
1.

CH3
2.
CH3CH2CH2CCH3

CH3CHCH2CH3

3. Draw 3, 5, 7 - Trimetyldecane
 Practice:
1. 3, 3, 5 – Trimethyl Heptane

CH3
2.
CH3CH2CH2CCH3 3, 4, 4 – Trimethyl Heptane
CH3CHCH2CH3

3. Draw 3, 5, 7 - Trimetyldecane
Propyl vs. Isopropyl
• Starting from the bonding
point in a normal
propyl group there is a
continuous string of three
carbon atoms.
• Starting from the bond
point in an isopropyl group
the three carbon atoms are
not continuous, instead
they are branched.
Cycloalkanes
• Ring structures of alkanes
• Three or more carbon atoms
• Two LESS hydrogen atoms in the ring structure

Line Structure:
• Shows only the C-C bonds
• H atoms on the ring are not shown
• Example: cyclohexane
Naming Cycloalkanes
1. Name the ring (put cyclo- before alkane name)
2. Number the ring carbons from the first group
3. Name the groups with smallest set of numbers

CH3

CH3

CH3

CH3
CH2CH3
Naming Cycloalkanes
1. Name the ring (put cyclo- before alkane name)
2. Number the ring carbons from the first group
3. Name the groups with smallest set of numbers

CH3

CH3

CH3

CH3
CH2CH3
1, 2 – dimethyl cyclopentane 1-ethyl-1,2-dimethylcyclobutane
Properties of Alkanes
• Nonpolar
• Low melting and boiling points
• Not soluble in water
• Low reactivity
Saturated vs. Unsaturated Hydrocarbons
• Saturated Hydrocarbons:
have the maximum number
of hydrogen atoms attached
to each carbon atom
(alkanes)
• Unsaturated Hydrocarbons:
have fewer hydrogen atoms
attached to the carbon chain
than alkanes (contain at least
one double or triple bond)
Alkenes
• Alkene
• Contain one or more C = C double bonds
• General molecular formula CnH2n
• Suffix - ene
• Smallest alkene – ethylene
Naming Alkenes
1. Use the alkane naming system with a suffix –ene
2. Double bond MUST be in the longest chain
3. Number the carbons to get the lowest number on the double bond
4. If 2 C=C double bonds, use the suffix - diene
1, 3 - pentadiene
Properties of Alkenes
• Similar to alkanes
• More reactive due to the double bond
Alkynes
• Contain one or more C  C triple bonds
• General molecular formula CnH2n-2
• Smallest alkynes …. Common name acetylene
• Ethyne: H--CC—H

• Properties of Alkynes
• Similar to alkanes and alkenes
• Even more reactive due to the triple bond
• Naming Alkynes
• Same as before – suffix -yne
Practice:
Practice:
Isomers
• Isomer: structures that have the same molecular
formula but different structure

• Two types
• Structural
• Stereoisomers
Structural Isomers
• Molecules with same chemical formula, but different molecular structures
• Structural isomers differ in physical properties such as boiling point and
melting point. They also have different chemical reactivities.

• Both butane and 2-methylpropane have the molecular formula C4H10.

Draw 3 isomers of C5H12
Draw the isomers of C4H8
Stereoisomers
• Stereoisomers: molecules in which the atoms are joined in the same
order, but the positions of the atoms in space are different.

• Two types
• Geometric isomers
• Optical isomers
Geometric Isomers
• Geometric isomers have atoms joined in the same order, but differ in
the orientation of groups around a double bond.

• Across the double bond, two different conformations can exist

• The inflexible double bond does not allow for rotation
Cis/Trans Configurations
• In the trans configuration, the methyl groups are on opposite sides of the double bond.
• In the cis configuration, the methyl groups are on the same side of the double bond.

• The groups attached to the carbons of the double bond do not need to be the same.
• Geometric isomerism is possible whenever each carbon of the double bond has at least
one substituent
• There is a trans and a cis configuration of 2-butene because
a methyl group is attached to each carbon of the double
bond.
Optical Isomers
• Carbon atom has four different atoms or groups attached
• A carbon with four different atoms or groups attached is an
asymmetric carbon.

• Pairs of molecules that differ only in the way that four different groups
are arranged around a central carbon atom are called optical
isomers.
Aromatic Hydrocarbons
• Also known as an arene
• Contain the benzene ring C6H6
• Carbon atoms are joined together by alternating single and double covalent bonds
within a cyclic hydrocarbon

• Benzene structure is very stable due to the resonance in the ring (that
bonds don’t actually alternate and all six bonds are identical)
• Ring bonds do not break
• H atoms on the ring are replaced w/ R-groups (side groups)
Substituted Aromatic Compounds
• Compounds with a substituent on a benzene ring are named as a
derivative of benzene. When benzene is a substituent, it is called a
phenyl group.
Disubstituted benzene
• Dimethyl benzenes are also called xylenes
• Positions of the disubstitutes can be 1,2; 1,3; or 1,4.
• Common names for these benzenes use the terms ortho, meta, and para in
place of number
Polymers
• Long-chain molecules consisting of many replacing units

• Natural Polymers:
• Cellulose in plants
• Starches in foods
• Proteins & DNA in the body

• Synthetic Polymers:
• Polyethylene & polystyrene (plastics)
• Nylon
• Teflon