Chapter 11 Introduction to Organic

Chemistry: Hydrocarbons
Organic Compounds

• Originally the chemistry of living or once-lived

• Now, The Chemistry of C-containing compounds.
• also contain H, O, S, N, and halogens (F, Cl, Br, I).

• Friedrich Wohler

1
Organic vs. Inorganic

2
 Writing Formulas for Alkanes
CH4 = methane
C has 4 valence electrons and H
has 1 (there are 4 of them) = 8 valence
electrons
•
•C• •H
•
• carbon achieves an octet by forming
four bonds.

3
Hydrocarbons

Alkanes

Alkenes

Alkynes

Aromatics
4
Prefix = Number of Carbons
# Carbons Prefix

1 6

2 7

3 8

4 9

5 10

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Names of Alkanes
The names of alkanes
 determined by IUPAC (International Union of Pure and Applied Chemistry)
Prefix + ane.
Name # Carbons Expanded Structural Formula Condensed
1

3
General Formula:

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 Names of Alkanes
Alkanes with 5-10 carbon atoms in a chain use Greek prefixes.
Name # Carbons Structural Formula Line Angle
Butane 4 CH3CH2CH2CH3
Pentane 5 CH3CH2CH2CH2CH3
Hexane 6 CH3CH2CH2CH2CH2CH3
Heptane 7 CH3CH2CH2CH2CH2CH2CH3
Octane 8 CH3CH2CH2CH2CH2CH2CH2CH3
Nonane 9 CH3 CH2 CH2CH2CH2CH2CH2CH2CH3
Decane 10 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

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 Cycloalkanes

8
 Name the following

A. CH3─CH2─CH2─CH3

B.

C. CH3─CH2─CH2─CH2─CH2─CH2─CH2─CH3

D.

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 Draw Structures
A. pentane

B.cyclopentane

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More Complex Alkanes
1. Find the longest chain in the molecule =
parent
2. List the substituents (alphabetical order)
3. Number the chain from the end nearest the
first substituent encountered.
4. Number the substituents.

Butanes:

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Name the following
Draw Structures

1-bromo-3-chlorobutane 3-ethyl-3-methylhexane

2,2,4-trimethylpentane 1,1,1,2-tetrafluoroethane
Cyclic Compounds

CH3

1,3,5-trichlorocyclopentane 1-iodo-2-isopropylcyclopropane

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Some Properties of Alkanes
Alkanes with 1-4 carbon.
• gases at room temperature.
• used as heating fuels.

Alkanes with 5-8 carbon atoms

• liquids at room temperature.
• pentane, hexane, heptane, and octane.
• very volatile.
• used to make gasoline.

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Some Properties of Alkanes
Alkanes with 9-17 carbon atoms
• are liquids at room temperature
• have higher boiling points.
• are found in kerosene, diesel, and jet fuels.

Alkanes with 18 or more carbon atoms

• have high molar masses.
• are waxy solids at room temperature.
• used in waxy coatings of fruits and vegetables.

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Unsaturated Hydrocarbons

Saturated hydrocarbons
• maximum number of hydrogen atoms
• alkanes and cycloalkanes with single C-C
bonds.
CH3—CH2—CH3
Unsaturated hydrocarbons
• fewer hydrogen atoms attached to the carbon
chain than alkanes.
• alkenes and alkynes

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Naming Alkenes

At least one C=C

• use the corresponding alkane name.
• change the ending to –ene.
Alkene IUPAC Common
ethene ethylene

propene propylene

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 Naming Alkynes
The names of alkynes
• use the corresponding alkane name.
• change the ending to –yne.
Alkyne IUPAC Common
ethyne acetylene

propyne

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 Naming Alkenes and Alkynes
What if the double (or triple) bond can be in more that one place?

CH2=CH─CH2─CH3

CH3─CH=CH─CH3

CH3─CH2─CC─CH3

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Name the following . . .

21
 Draw structures of the following . . .

3-methyl-1-pentyne

5,5-dichloro-2-heptene

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 Naming Cis-Trans Isomers

The prefix of cis or trans is placed in front of the alkene

name when the compound is a cis or trans isomer.
cis trans

Br Br Br H
C C C C
H H H Br

cis-1,2-Dibromoethene trans-1,2-Dibromoethene
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 Not Cis-Trans Isomers

• Alkenes cannot have cis-trans isomers if a carbon atom in the

double bond is attached to identical groups.
Identical Identical

HH Br
H
Br H Br
C C C C
HH CH3 H Br
2-Bromopropene 1,1-Dibromoethene
(not cis or trans) (not cis or trans)

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 Cis- , Trans- , or Neither

25
 Use cis- and trans- to name

Br Br
A. C C
H H

CH3 H
B. C C
H CH3

CH3 Cl
C. C C
H Cl
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Addition Reactions of Alkenes

 One reaction of alkenes is the addition reaction.

 two atoms add across the double bond.
 One -bond and one -bond are replaced by two -bonds.
 Hydrogenation (H–H)
 Hydration (H–OH)
 Polymerization
 Hydrogenation

• H atoms add to the carbon atoms of a double bond or triple

bond.
• a catalyst such as Pt or Ni is used to speed up the reaction.

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 Hydrogenation of Oils
Adding H2 to double
bonds in vegetable
oils produces

• compounds with higher

melting points.
• solids at room temperature,
such as margarine,
soft margarine,
and shortening.

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What are the products?

Pt
CH3─CH=CH─CH3 + H2

Pt
+ H2

30
Hydration
- Requires an acid catalyst (H+)
- alkene  alcohol

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 Naming Aromatic Compounds
Aromatic compounds are named
• with benzene as the parent chain.
• with one side group named in front of benzene.

chlorobenzene

32
 Special Aromatic Compounds
Old names allowed by IUPAC

33
Naming Aromatic Compounds
When two groups are attached to the benzene ring, the ring is
numbered to give the lowest numbers to the side groups.

34
 What are the structures?

A. 1,3-dibromobenzene

B. 4-chlorotoluene

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Aromatic Compounds in Nature and Health

Vanillin O Aspirin O
CH COH O
C O CH3

OCH3
O
OH
NH C CH3
Ibuprofen Acetaminophen
CH3 CH3 O
H3C CH CH2 CH COH
OH

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