Organic Compounds - Handouts PDF

14/03/2020
Introduction to Organic
Chemistry: Alkanes
Organic Compounds
General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. 1
Organic Compounds
An organic compound
 is a compound made from carbon atoms
 has one or more C atoms
 has many H atoms
 may also contain O, S, N, P, and halogens
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Properties of Organic Compounds

Typical organic compounds
 contain carbon
 have covalent bonds
 have low melting points
 have low boiling points
 are flammable
 are soluble in nonpolar
solvents
 are not soluble in water Oil (organic) and
water (inorganic)
General, Organic, and Biological Chemistry 3
Organic versus Inorganic

Compounds
 Propane, C3H8, is an
organic compound used
as a fuel.
 NaCl, salt, is an inorganic
compound composed of
Na+ and Cl– ions.
Question: Why is propane

an organic compound, but
NaCl is not?
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Comparing Properties of Organic

and Inorganic Compounds
Learning Check
Identify each of the following characteristics as most
typical of compounds that are I) inorganic or O) organic.
___ 1. has a high melting point
___ 2. is not soluble in water
___ 3. has a formula CH3─CH2─CH3
___ 4. has a formula MgCl2
___ 5. burns easily in air
___ 6. has covalent bonds
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Solution
Identify each of the following characteristic as most

typical of compounds that are I) inorganic or O) organic.
I 1. has a high melting point
O 2. is not soluble in water
O 3. has a formula CH3─CH2─CH3
I 4. has a formula MgCl2
O 5. burns easily in air
O 6. has covalent bonds
Writing Formulas for Carbon

Compounds
In carbon compounds,
 carbon has 4 valence electrons, and hydrogen has 1
•
•C• H•
•
 to achieve an octet, C forms four bonds
H H

HCH H C H

H H CH4 (methane)
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Organic Compounds with More

Carbon Atoms
In organic molecules with more carbon atoms,
 valence electrons are shared
 covalent bonds form between carbon and carbon atoms
 covalent bonds form between carbon and hydrogen
atoms
H H H H
•• ••
HCCH H C C H
•• ••
H H H H CH3─CH3 (methane)
Chemistry: Alkanes
Functional Groups
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Elements in Organic Compounds

In organic molecules, C atoms form bonds
 mostly with H and other C atoms
 sometimes with atoms of O, S, N, P, and halogens F,
Cl, and Br
Functional Groups
Functional groups
 are a characteristic feature of organic molecules
that behave in a predictable way
 are composed of an atom or group of atoms
 are groups that replace a H in the corresponding
alkane
 provide a way to classify families of organic
compounds
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Some Functional Groups
Alkenes and Alkynes

 Alkenes contain a double bond
between adjacent carbon atoms.
 Alkynes contain a triple bond.
 Aromatic compounds contain a

benzene ring.
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Alcohols and Ethers

 An alcohol contains the
hydroxyl (–OH) functional
group.
 In an ether, an oxygen atom

is bonded to two carbon
atoms (–C–O–C–).
Thiols
 In a thiol, the functional group
–SH is bonded to a carbon
atom.
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Aldehydes and Ketones

 An aldehyde contains a
carbonyl group (C=O), which
is a carbon atom with a double
bond to an oxygen atom,
attached to at least one
hydrogen.
 In a ketone, the carbon of the

carbonyl group is attached to
two other carbon atoms.
Carboxylic Acids and Esters

 Carboxylic acids contain the
carboxyl group, which is a carbonyl
group attached to a hydroxyl group.
O

— C—OH
 An ester contains the carboxyl
group between carbon atoms.
O

— C—O—
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Amines and Amides

 In an amine, the functional
group is a nitrogen atom.
|
—N—
 In an amide, the hydroxyl

group of a carboxylic acid is
replaced by a nitrogen group.
O
 
— C—N—
19
General, Organic, and Biological Chemistry
Learning Check
Classify each of the following as alcohol, ether,
aldehyde, ketone, carboxylic acid, ester, or amine.
1) CH3–CH2–CH2–OH
2) CH3–O–CH2–CH3
3) CH3–CH2–NH2
O
||
4) CH3–C–OH
O
||
5) CH3–C–O–CH3
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Solution
Classify each of the following as alcohol, ether,
aldehyde, ketone, carboxylic acid, ester, or amine.
1) CH3─CH2─CH2─OH
alcohol
2) CH3─O─CH2─CH3
ether
3) CH3─CH2─NH2 amine
O O
|| ||
4) CH3─C─OH 5) CH3─C─O─CH3
carboxylic acid ester
Chemistry: Alkanes
Alkanes
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Chemistry: Alkanes
Properties of Alkanes
Some Properties of Alkanes

The properties of alkanes
include being
 nonpolar
 insoluble in water
 less dense than water
 flammable in air
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Alkanes with 1–4 Carbon Atoms

Alkanes with 1–4 carbon atoms are
 methane, ethane, propane, and
butane
 gases at room temperature
 used as heating fuels
Alkanes with 5–17 Carbon Atoms
Alkanes with 5–8 carbon atoms are

 liquids at room temperature
 pentane, hexane, heptane, and octane
 very volatile
 used to make gasoline
Alkanes with 9–17 carbon atoms

 are liquids at room temperature
 have higher boiling points
 are found in kerosene, diesel, and jet fuels
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Alkanes with 18 or More Carbon

Atoms
Alkanes with 18 or more carbon atoms
 have high molar masses
 are waxy solids at room temperature
 are used in waxy coatings of fruits and
vegetables
Boiling Points of Alkanes

Boiling points of alkanes
 are lowest of the organic compounds
 increase with larger molecules due to increased
dispersion forces
 decrease for branched alkanes
 increase for cycloalkanes
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Boiling Points of Alkanes with 5

Carbons
Learning Check
For the following pairs of hydrocarbon, which one has
the higher boiling point? Why?
A. Butane or octane
B. Hexane or 2,3-dimethylbutane
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Solution
For the following pairs of hydrocarbon, which one has
the higher boiling point? Why?
A. Butane or octane
octane (has more carbon atoms)
B. Hexane or 2,3-dimethylbutane
hexane (both have 6 carbons, but hexane
is not branched)
Crude Oil
The hydrocarbons in crude oil are
 separated by their different boiling points
 heated to higher temperatures to produce gases
that can be cooled and removed
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Crude Oil (continued)
Combustion of Alkanes
Alkanes
 undergo combustion
by reacting with oxygen
to produce carbon
dioxide, water, and
energy
 are typically not very
reactive due to strong
C—C single bonds
Alkane + O2(g) CO2(g) + H2O(g) + energy
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Balancing A Combustion Equation

Write the equation:
C5H12(l) + O2(g) CO2(g) + H2O(g)
Balance C:
C5H12(l) + O2(g) 5CO2(g) + H2O(g)
Balance H:
C5H12(l) + O2(g) 5CO2(g) + 6H2O(g)
Balance O with O2:

C5H12(l) + 8O2(g) 5CO2(g) + 6H2O(g)
Learning Check
Propane is used to provide
heat for cooking or warming
a room. Write a balanced
equation for the complete
combustion of propane.
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Solution
Unbalanced equation:
C3H8(g) + O2(g) CO2(g) + H2O(g)
Balance C:
C3H8(g) + O2(g) 3CO2(g) + H2O(g)
Balance H:
C3H8(g) + O2(g) 3CO2(g) + 4H2O(g)
Balance O:
C3H8(g) + 5O2(g) 3CO2(g) + 4H2O(g)
Learning Check
Write a balanced equation for the reaction for the
complete combustion of heptane, C7H16.
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Solution
Write a balanced equation for the reaction for the
complete combustion of heptane, C7H16.
C7H16(l) + O2(g) CO2(g) + H2O(g)
C7H16(l) + O2(g) 7CO2(g) + 8H2O(g)
C7H16(l) + O2(g) 7CO2(g) + 8H2O(g)
C7H16(l) + 11O2(g) 7CO2(g) + 8H2O(g)
Balanced equation:
C7H16(l) + 11O2(g) 7CO2(g) + 8H2O(g)
Names of Alkanes
The names of alkanes
 are determined by the IUPAC (International Union of
Pure and Applied Chemistry) system
 use a prefix to indicate the number of carbons in a
chain
 end in -ane
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IUPAC Names for Alkanes
Learning Check
A. Give the name of each compound:
1) CH3—CH3
2) CH3—CH2—CH3
3) CH3—CH2—CH2—CH2—CH2—CH3
B. Write the condensed structural formula of pentane.
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Solution
A. Give the name of each compound:
1) CH3—CH3 ethane
2) CH3—CH2—CH3 propane
3) CH3—CH2—CH2—CH2—CH2—CH3 hexane
B. Write the condensed structural formula of pentane.

CH3—CH2—CH2—CH2—CH3
Structural Formulas
Alkanes are written with structural formulas that are

 expanded to show each bond
 condensed to show each carbon atom and the
attached hydrogen atoms
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Line-Bond Formulas
 Because each C atom has a tetrahedral

arrangement, the order of atoms is not a straight
line, but a zigzag pattern.
 A line-bond formula abbreviates the carbon atoms
and shows only the zigzag pattern of bonds from
carbon atom to carbon atom.
Types of Structural Formulas
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Writing Structural Formulas

Carbon atoms in a chain
 maintain their tetrahedral shape
 are connected in a zigzag pattern
 are drawn as two-dimensional
 can be written in several conformations
Structural Arrangements of
Butane
 Rotation of the end CH3-groups provides different
structural arrangements for butane.
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Hexane has Six Carbon Atoms

Hexane
 is an alkane with 6 carbon atoms in a continuous
chain
 has a “zigzag” look because each carbon atom is at
the center of a tetrahedron
 is represented by a ball-and-stick model as
Learning Check
A. Draw the condensed structural formula of
H H H H H
H C C C C C H
H H H H H
B. What is its molecular formula?
C. What is its name?
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Solution
A. Draw the condensed structural formula:
CH3─CH2─CH2─CH2─CH3
B. What is its molecular formula? C5H12
C. What is its name? pentane
Learning Check
Draw the condensed structural formula for:
A. Ethane
B. Heptane
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Solution
Draw the condensed structural formula for:
A. Ethane CH3─CH3
B. Heptane CH3─CH2─CH2─CH2─CH2─CH2─CH3
Cycloalkanes
Cycloalkanes
 are cyclic alkanes
 have 2H fewer than the alkane
 are named by using the prefix cyclo- before the
name of the alkane chain with the same number of
carbon atoms
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Cycloalkanes (continued)
The structural formulas
of cycloalkanes
 are often shown as
geometric figures
Cycloalkanes (continued)
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Learning Check
Name the following:
A. CH3─CH2─CH2─CH3
B.
C. CH3─CH2─CH2─CH2─CH2─CH2─CH2─CH3
D.
Solution
Name the following:
A. CH3─CH2─CH2─CH3 butane
B. cyclopropane
C. CH3─CH2─CH2─CH2─CH2─CH2─CH2─CH3 octane
D.
cyclohexane
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Chemistry: Alkanes
Alkanes with Substituents
Isomers of Butane
Isomers
 have the same molecular
formula
 have different structural
arrangements
 of butane (C4H10) consist
of a straight chain and a Branch or
branched chain each with substituent
4 carbon atoms
General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.
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Substituents
Substituents are
 attached to carbon chains
 carbon branches that are missing one H and named
as alkyl groups
 halogen atoms that are named as halo substituents
Alkanes with Alkyl Groups

CH3
CH3—CH—CH3 methylpropane
methyl groups
CH3 CH3
CH3—CH—CH2—CH—CH3 2,4-dimethylpentane
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Naming Alkanes with Substituents
Example of Naming Alkanes

Give the name of CH3
CH3─CH─CH2─CH3
STEP 1 Write the name of the longest chain: butane
STEP 2 Number the chain from the end nearer a branch:
CH3
CH3─CH─CH2─CH3
1 2 3 4
STEP 3 Give location and names of substituents:
2-Methylbutane
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Learning Check
Write the IUPAC name for:
Cl CH3
CH3─CH2─CH─CH─CH3
Solution
STEP 1 Write the name of the longest chain:
pentane
STEP 2 Number chain from end nearer substituents:
Cl CH3 (nearer end)
CH3─CH2─CH─CH─CH3
5 4 3 2 1
STEP 3 Give location and name substituents

alphabetically:
3-Chloro-2-methylpentane
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Learning Check
Give the IUPAC name for each of the following:
A. CH3 CH3
| |
CH3─CH─CH2 ─CH─CH2─CH3
B. Cl CH3
| |
CH3─CH2─CH─CH2─C─CH2─CH3
|
Cl
Solution
A. CH3 CH3
| |
CH3─CH─CH2 ─CH─CH2─CH3 2,4-dimethylhexane
1 2 3 4 5 6
B. Cl CH3 more substituents on C3

| |
CH3─CH2─CH─CH2─C─CH2─CH3
|
Cl
7 6 5 4 3 2 1
3,5-dichloro-3-methylheptane
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Guide to Drawing Alkane Structures
What Is in a Name?
The structural formula is drawn from the IUPAC name.
2,4-dimethylhexane
2,4 dimethyl hexane

Location of Two CH3-groups 6-carbon main chain
branches on attached with single C—C
bonds main chain
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Learning Check
Draw the condensed structural formula for
3-bromo-1-chlorobutane.
Solution
STEP 1 Draw a chain with 4 carbon atoms:
C─C─C─C
STEP 2 Number the chain and add substituents:
Br

C ─ C ─ C ─ C ─ Cl
4 3 2 1
STEP 3 Add hydrogen (H) to give four bonds to each C:
Br

CH3─CH─CH2─CH2─Cl
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Naming Cycloalkanes with

Substituents
The name of a substituent is placed in front of the
cycloalkane name.
CH3
Methylcyclobutane
When there are two substituents, number the ring

1-bromo-2-chlorocyclopentane
Br
Cl
Learning Check
Name each of the following:
1. CH3
CH2─CH3
2.
Cl
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Solution
Name each of the following:
1. CH3 methylcyclopropane
CH2─CH3
2.
Cl 3-Chloro-1-ethylcyclohexane
Learning Check
Write three isomers of C5H12, and name each.
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Solution
A chain of 5 carbon atoms: CH3─CH2─CH2─CH2─CH3
pentane
A chain of 4 carbon atoms and 1 carbon branch:
CH3
│
CH3─CH─CH2─CH3 2-methylbutane
A chain of 3 carbon atoms and 2 carbon branches:

CH3
│
CH3─C─CH3 2,2-dimethylpropane
│
CH3
39

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14/03/2020

Properties of Organic Compounds

General, Organic, and Biological Chemistry 3

Organic versus Inorganic

Question: Why is propane

General, Organic, and Biological Chemistry 4

Comparing Properties of Organic

General, Organic, and Biological Chemistry 5

Identify each of the following characteristic as most

Writing Formulas for Carbon

Organic Compounds with More

General, Organic, and Biological Chemistry 10

Elements in Organic Compounds

General, Organic, and Biological Chemistry 11

Some Functional Groups

General, Organic, and Biological Chemistry 13

Alkenes and Alkynes

 Alkynes contain a triple bond.

 Aromatic compounds contain a

General, Organic, and Biological Chemistry 14

Alcohols and Ethers

 In an ether, an oxygen atom

General, Organic, and Biological Chemistry 16

Aldehydes and Ketones

 In a ketone, the carbon of the

General, Organic, and Biological Chemistry 17

Carboxylic Acids and Esters

General, Organic, and Biological Chemistry 18

Amines and Amides

 In an amide, the hydroxyl

Some Properties of Alkanes

Alkanes with 1–4 Carbon Atoms

General, Organic, and Biological Chemistry 25

Alkanes with 5–17 Carbon Atoms

Alkanes with 5–8 carbon atoms are

Alkanes with 9–17 carbon atoms

Alkanes with 18 or More Carbon

General, Organic, and Biological Chemistry 27

Boiling Points of Alkanes

Boiling Points of Alkanes with 5

General, Organic, and Biological Chemistry 29

Crude Oil (continued)

General, Organic, and Biological Chemistry 33

Alkane + O2(g) CO2(g) + H2O(g) + energy

General, Organic, and Biological Chemistry 34

Balancing A Combustion Equation

Balance O with O2:

General, Organic, and Biological Chemistry 36

IUPAC Names for Alkanes

General, Organic, and Biological Chemistry 41

B. Write the condensed structural formula of pentane.

B. Write the condensed structural formula of pentane.

Alkanes are written with structural formulas that are

General, Organic, and Biological Chemistry 44

 Because each C atom has a tetrahedral

Types of Structural Formulas

General, Organic, and Biological Chemistry 46

Writing Structural Formulas