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Transcript of 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
1
Copyright © 2009 by Pearson Education, Inc.
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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)
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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EXAMPLE
Name the following molecules
Cl
Br
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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
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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.
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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
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EXAMPLESName the following.
A. CH3─CH2─CH2─CH3
B.
C.
D.35
H3CCH2
CHCH2
H2C
CH2
CH3
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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
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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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Copyright © 2009 by Pearson Education, Inc.
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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.
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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
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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)
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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
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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
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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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Copyright © 2009 by Pearson Education, Inc.
Amines
An amide
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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