c hapter 10 i ntroduction to o rganic c hemistry : a lkanes 10.1 organic compounds 1 copyright ©...
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CHAPTER 10 INTRODUCTION TO ORGANIC CHEMISTRY: ALKANES
10.1 Organic Compounds
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Copyright © 2009 by Pearson Education, Inc.
ORGANIC CHEMISTRY
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, and halogens.
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ORGANIC COMPOUNDS
Typical organic compounds
• have covalent bonds.• have low melting points.• have low boiling points.• are flammable.• are soluble in nonpolar
solvents.• are not soluble in water.
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oil (organic) and water (inorganic)
ORGANIC VS. INORGANIC
• Propane, C3H8, is an organic compound used as a fuel.
• NaCl, salt, is an inorganic compound composed of Na+ and Cl− ions.
Why is propane organic,
but NaCl is not?
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COMPARING ORGANIC AND INORGANIC COMPOUNDS
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EXAMPLES
Identify each characteristic as most typical of compounds
that are 1) inorganic or 2) organic.
A. has a high melting point.
B. is not soluble in water.
C. has a formula CH3─CH2─CH3.
D. has a formula MgCl2.
E. burns easily in air.
F. has covalent bonds.6
WRITING FORMULAS FOR ALKANESIn organic compounds, • carbon has 4 valence electrons and hydrogen has 1.
•
• C • H •
•
• carbon achieves an octet by forming four bonds. H H
H C H H C H
H H CH4, methane
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TETRAHEDRAL STRUCTURE OF CARBON
VSEPR theory predicts that a carbon atom with four single, covalent bonds has a tetrahedral shape.
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ORGANIC MOLECULESIn organic molecules, • valence electrons are shared.• covalent bonds form between carbon atoms.
H H H H • • • •
H C C H H C C H • • • • H H H H
Ethane, CH3─CH39
TETRAHEDRAL STRUCTURE OF CARBON
In molecules with two or more carbon atoms, each carbon atom with four single bonds has a tetrahedral shape.
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CHAPTER 10 INTRODUCTION TO ORGANIC CHEMISTRY: ALKANES
10.2 Alkanes
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10.2 – ALKANES
Structural Formulas Alkanes are written with structural formulas that are• expanded to show each bond.• condensed to show each carbon atom and its
attached hydrogen atoms.
Expanded Condensed H
H C H CH4 , methane
H
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STRUCTURAL FORMULAS Condensed formulas are written for
expanded structural formula by showing each carbon and the attached hydrogen atoms.
E.g C2H6
Expanded Condensed
H H │ │ H─C ─C ─ H CH3─CH3
│ │ H H
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EXAMPLE
Write an expanded formula and condensed formula for
C4H10
NAMES OF ALKANESThe names of alkanes • are determined by the IUPAC (International Union of
Pure and Applied Chemistry) system.• end in –ane.• with 1-4 carbons in a chain use prefixes as follows:
Name # Carbons Condensed Structural Formula
Methane 1 CH4
Ethane 2 CH3―CH3
Propane 3 CH3―CH2―CH3
Butane 4 CH3―CH2―CH2―CH3 15
NAMES OF ALKANESAlkanes with 5-10 carbon atoms in a chain use Greek prefixes.
Name # Carbons Structural Formula
Pentane 5 CH3CH2CH2CH2CH3
Hexane 6 CH3CH2CH2CH2CH2CH3
Heptane 7 CH3CH2CH2CH2CH2CH2CH3
Octane 8 CH3CH2CH2CH2CH2CH2CH2CH3
Nonane 9 CH3 CH2 CH2CH2CH2CH2CH2CH2CH3
Decane 10 CH3CH2CH2CH2CH2CH2CH2CH2CH2CH316
WRITING STRUCTURAL FORMULAS
Carbon atoms in a chain• maintain tetrahedral shape.• are connected in a zigzag pattern.• are drawn as 2-dimensional. • can be written in several conformations
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HEXANE HAS SIX CARBON ATOMS
Hexane • is an alkane with six 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 shown
below.
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=
Skeletal formula
Ball-and-stick
EXAMPLES
Write the condensed and skeletal formula for
A. ethane.
B. heptane.
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EXAMPLES
A. Write the condensed formula for:
B. What is its molecular formula?
C. What is its name?
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CYCLOALKANES
Cycloalkanes
• are cyclic alkanes.
• have two hydrogen atoms fewer than the open chain.
• 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
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The structural formulas of cycloalkanes are usually represented by geometric figures.
H2C
H2C CH2
H2C
H2C CH2
CH2
H2C
H2C
H2CCH2
CH2
CH2
Condensed formula
Skeletal formula
10.3 ALKANES WITH SUBSTITUENTS
Isomers of Butanehave the same
molecular formula.• have different atom
arrangements.
• of butane (C4H10) are a straight chain and a branched chain.
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H3CCH2
H2C
CH3
H3CCH
CH3
CH3
ALKYL GROUPS Alkyl groups are• alkanes that are missing one H. • substituents attached to carbon chains.• named with a –yl ending.
CH3 methyl
CH3 CH2 ethyl
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ALKANES WITH SUBSTITUENTS
CH3
CH3 CH CH3 methylpropane
methyl groups
CH3 CH3
CH3 CH CH2 CH CH3
2,4-dimethylpentane25
NAMING SUBSTITUENTS
In the IUPAC system,• a carbon branch is
named as an alkyl group.
• halogen atoms are named as halo.
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NAMING HALO-ALKANES
Step 1: determine the long chain Name it as parent chain
Step 2: identify substituents Akyl – all CH Halo – halogen
Chlorine Chloro Bromine bromo
number carbon starting from the end closet to the substituent
Step 3: name the molecule in alphabetical order. Location-substituentparent chain
NAMING ALKANESGive the name of CH3 CH3
CH3─CH─CH─CH3
STEP 1: Name the longest continuous chain.
STEP 2: Number chain.
STEP 3: Locate substituents and name. 28
EXAMPLE
Name the following molecules
Cl
Br
EXAMPLE
Write the name of
Cl CH3
CH3─CH2─CH─CH─CH3
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LEARNING CHECKGive the IUPAC name for each of the following:
A. CH3 CH3
| |
CH3─CH─CH2 ─CH─CH3
B. Cl CH3 | |
CH3─CH2─CH─CH2─C─CH2─CH3
|
Cl31
LEARNING CHECKDraw the condensed structural formula for 3-bromo-1-chlorobutane.
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STEP 1: Longest chain has 4 carbon atoms.
STEP 2: Number chain and add substituents.
TEP 3: Add hydrogen to complete 4 bonds to each C.
NAMING CYCLOALKANES WITH SUBSTITUENTS
The name of a substituent is placed in front of the
cycloalkane name. CH3
methylcyclobutane
Cl
Chlorocyclopentane
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LEARNING CHECK
Name each of the following.
1. CH3
CH2─CH3
2.
3.34
F
EXAMPLESName the following.
A. CH3─CH2─CH2─CH3
B.
C.
D.35
H3CCH2
CHCH2
H2C
CH2
CH3
10.4 PROPERTIES OF ALKANES
Alkanes are• nonpolar.• insoluble in water.• less dense than water.• flammable in air.
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SOME PROPERTIES OF ALKANES
Alkanes with 1-4 carbon atoms are
• methane, ethane, propane, and butane.
• gases at room temperature.
• used as heating fuels.
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SOME PROPERTIES OF ALKANES
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.38
SOME PROPERTIES OF ALKANES
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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COMBUSTION
In combustion reactions,
• alkanes react with oxygen.
• CO2, H2O, and energy are produced.
• Alkane + O2 CO2 + H2O + heat
40Copyright © 2009 by Pearson Education, Inc.
LEARNING CHECK
Write a balanced equation for thecomplete combustion of a. Propane
b. Octane
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10.5 FUNCTIONAL GROUPS
In organic molecules, carbon atoms bond • with four bonds.• mostly with H and other C atoms.• sometimes to O, N, S. • sometimes to halogens F, Cl, and Br.
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FUNCTIONAL GROUPS
Functional groups are• a characteristic feature of organic molecules that
behave in a predictable way. • composed of an atom or group of atoms. • groups that replace a hydrogen atom in the
corresponding alkane.• a way to classify families of organic compounds.
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ALKENES, ALKYNES, AND AROMATIC COMPOUNDS
Alkenes contain a double bond between adjacent carbon atoms.Alkynes contain a triple bond.Aromatic compounds contain a ring of six carbon atoms called benzene.
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C C C C
alkene alkynearomatic
H
H
H
HH H
H
H
H
H
H
H
COMPARING ALKENES, ALKYNES, AND AROMATIC COMPOUNDS
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ALCOHOLS AND ETHERS
An alcohol contains the hydroxyl (-OH) functional group.
A thiol contains the thiol (-SH) functional group.
An ether contains an oxygen atom bonded to two carbon atoms.
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R OH
Alcohol
R SH
thiol
R O R
ether
R = alkyl groups (carbon groups)
ALDEHYDES AND KETONESAn aldehyde contains a carbonyl group (C=O), which is a carbon atom with a double bond to an oxygen atom. The carbonyl is attached to a hydrogen.
In a ketone, the carbon of the carbonyl group (C=O) is attached to two carbon atoms.
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RC
O
HAldehyde
RC
O
RKetone
CARBOXYLIC ACIDS AND ESTERS
Carboxylic acids contain the carboxyl group, which is a carbonyl group attached to a hydroxyl group.
O ║
— C—OHAn ester contains the carboxyl group between carbon atoms.
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RC
O
OH
carboxylic
RC
O
O
ester
R
AMINES AND AMIDES
In amines, the functional group is a nitrogen atom. |
—N —
In amides, the hydroxyl group of a carboxylic acid is replaced by a nitrogen group.
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Amines
An amide
SUMMARY OF FUNCTIONAL GROUPS
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LEARNING CHECK
Classify each of the following as: alcohol, ether, aldehyde, ketone, carboxylic acid, ester, amine, or amide.
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O OH
HO
OO
O