12.1 Alkanes
Alkanes
Alkanes
Alkanes: Contain only C and H. Have only single CC bonds. Have a general formula of CnH2n +2.
C Atoms 1 3 6
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Structural Formulas
Structural formulas show the arrangement of atoms in an organic compound. In expanded structural formulas, all the individual bonds are drawn. In condensed structural formulas, each carbon is written with the H atoms connected to it. H H | | HC = CH3 C = CH2 | | H H
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Line-Bond Formulas
Because each C atom has a tetrahedral arrangement, the geometrical arrangement of carbon atoms is not a straight line. A line-bond formula abbreviates the carbon chain and shows only the zigzag pattern of bonds from carbon atom to carbon atom.
Summary of Formulas
Learning Check
A. Give the name of each compound: 1) CH3CH3 2) CH3CH2CH3 3) CH3CH2CH2CH2CH2CH3 B. Write the condensed structural formula of pentane.
Solution
A. Give the name of each compound: ethane 1) CH3CH3 2) CH3CH2CH3 propane 3) CH3CH2CH2CH2CH2CH3 hexane B. Write the condensed structural formula of pentane. CH3CH2CH2CH2CH3
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Learning Check
A. What is the condensed formula for H H H H | | | | H CCCCH | | | | H H H H B. What is its molecular formula? C. What is its name?
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Solution
A. CH3CH2CH2CH3 B. C4H10 C. butane
Conformations
As the groups attached to a C-C single bond rotate around the bond, their relative arrangements has different conformations.
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Conformations of Butane
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Learning Check
For propane, write the: 1) Molecular formula 2) Expanded structural formula 3) Condensed structural formula (two conformations) 4) Line-bond formula
Solution
1) Molecular formula C3H8 2) Expanded structural formula
H H H | | | H CCCH | | | H H H
4) Line-bond formula
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or
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Chapter 12 Alkanes
12.2 IUPAC Naming System for Alkanes 12.3 Drawing Structural Formulas
CH3 CH3 | | CH3CHCH2CHCH3 2,4-dimethylpentane
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Branched-Chain Alkanes
In a branchedchain alkane, a side group called a branch or a branch substituent is attached to a carbon chain.
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Alkyl Groups
An alkyl group: Is composed of one or more carbon atoms attached to a carbon chain. Is derived from the corresponding alkane by removing one hydrogen. Is named by replacing the ane ending of the corresponding alkane with yl. Derived from methane is methyl and from ethane is ethyl.
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Alkyl Groups
Naming Summary
In the IUPAC system: The longest chain is named as the main chain. Any carbon branches use their alkyl names. Each branch is numbered by counting the main chain from the end nearest the first side group. Branches are listed in alphabetical order.
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Learning Check
Give the IUPAC name for each alkane. A. CH3 CH3 | | CH3CHCH2CHCH3 B. CH2CH3 CH3 | | CH3CH2CHCH2CCH2CH3 | CH3
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Solution
A. CH3 CH3 | | CH3CHCH2CHCH3 2,4-dimethylpentane CH2CH3 CH3 | | CH3CH2CHCH2CCH2CH3 | CH3 5-ethyl-3,3-dimethylheptane
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What Is In A Name?
The structural formula is drawn from the IUPAC name. 2, 4-dimethylhexane
B.
2, 4
Location of branches on main chain
dimethyl
Two CH3- groups attached
hexane
6 carbon main chain with single C-C bonds
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Learning Check
Draw the condensed structural formula for A. 2, 3-dimethylbutane
B. 2, 3, 4-trimethylpentane
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Solution
Write the condensed structural formula for A. 2, 3-dimethylbutane CH3 CH3 | | CH3CHCHCH3 B. 2, 3, 4-trimethylpentane CH3 CH3 CH3 | | | CH3CHCHCHCH3
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Writing Isomers
The constitutional isomers for C4H10 can be written by first writing the continuous chain. Then remove one CH3 and attach it as a branch. CH3 | CH3CHCH3 CH3CH2CH2CH3 Butane 2-Methylpropane
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Learning Check
Write 3 constitutional isomers of C5H12 and name each.
Solution
CH3CH2CH2CH2CH3 pentane CH3 | CH3CHCH2CH3 2-methylbutane CH3 | CH3CCH3 | CH3
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2,2-dimethylpropane
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Chapter 12
Alkanes
Haloalkanes
In a haloalkane, one or more H atoms in an alkane is replaced by a halogen atom. Simple haloalkanes are named alkyl halides. In IUPAC names, a halogen is named as fluoro, chloro, bromo, or iodo. CH3Br bromomethane (methyl bromide) Cl | CH3CHCH2CH3 2-chlorobutane (sec-butyl chloride)
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12.4 Haloalkanes
Substituents
Naming of Haloalkanes
Methane compounds with two or more chlorine atoms are sometimes named by common names that do not reflect their structures.
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Learning Check
The name of this compound is: Cl CH3 | | CH3CH2CHCH2CHCH3 1) 2,4-dimethylhexane 2) 3-chloro-5-methylhexane 3) 4-chloro-2-methylhexane
Solution
The name of this compound is: Cl CH3 | | CH3CH2CHCH2CHCH3 3) 4-chloro-2-methylhexane
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Learning Check
Give the IUPAC name for each. A. CH3CH2F Br Cl | | B. CH3CHCHCH3
Solution
Give the IUPAC name for each. A. CH3CH2F fluoroethane Br Cl | | B. CH3CHCHCH3 2-bromo-3-chlorobutane
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Learning Check
Halothane is widely used as an anesthetic, which is a compound that decreases the ability of the nerve cells to conduct pain. What is the IUPAC name of halothane? F Br | | FCCCl | | F H
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Solution
The IUPAC name is 2-bromo-2-chloro-1,1,1-trifluoroethane. F Br | | FCCCl | | F H
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Chlorofluorocarbons (CFCs)
The ozone (O3) layer in the atmosphere absorbs most of the suns harmful radiation. Chlorofluorocarbons (CFCs) cause reactions that destroy the ozone layer. CFCs such as Freon-12 (CF2Cl2) have been used in refrigeration, air conditioning, and foam insulation. The use of CFCs in spray cans is no longer allowed.
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In the stratosphere, the CFCs are cleaved by the high-energy UV radiation from the sun.
UV light
CF2Cl2 CF2Cl + Cl The Cl reacts with ozone (O3). The ClO produced destroys another O3 forming additional Cl. Thus one Cl can destroy many O3 molecules. Cl + O3 ClO + O2 ClO + O3 Cl + 2O2
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Chapter 12
Alkanes
According to the National Academy of Sciences, each 1% loss of ozone (O3) increases the amount of UV radiation reaching the earth by 2%. More UV radiation means more skin cancer and cataracts in humans, more intense photochemical smog, and lower crop yields.
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12.5 Cycloalkanes
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Cycloalkanes
Cycloalkanes: Are rings of carbons that can be drawn as geometric figures. Have a general formula of CnH2n or 2 H less than the alkane. propane C3H8 cyclopropane C3H6. butane C4H10 cyclobutane C4H8. Are named with the prefix cyclo- in front of the corresponding alkane name.
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Formulas of Cycloalkanes
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Naming Cycloalkanes
A cycloalkane with: One substitutuent is named by placing the name of the substituent in front of the cycloalkane name. Two or more substitutuents is named by numbering the ring in the direction that gives the lower numbers to the substituents.
Learning Check
Name each of the following cycloalkanes.
CH3
Solution
Name each of the following cycloalkanes.
CH3
1,2-dimethylcyclobutane
CH3 Cl Cl CH3
chlorocyclopentane
Cl
Cl
1-chloro-3-methylcyclohexane
CH3
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CH3
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Constitutional Isomers
Cis-Trans Isomers
The rigid ring in a cyclic structure prevents rotation of substitutuents bonded to the ring. A cyclic structure with two substituents has two isomers called cis-trans isomers. The cis isomer, has two substituents on the same side of the ring. The trans isomer, has two substituents on opposite sides of the ring.
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The compound 1,2-dichlorocyclopropane has cis-trans isomers. Cl atoms on Cl atoms on same side opposite sides
Cl
Cl
Cl Cl
cis-1,2-dichlorocyclopropane
` -1,2-dichlorocyclopropane trans
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Learning Check
Name each as a cis or trans isomer.
Br Br Cl
Br
Solution
Name each as a cis or trans isomer.
Br Cl
trans-1,2-dibromocyclopropane cis-1,3-dichlorocyclobutane
Cl
Cl
Cl
Cl
trans-1-bromo-3-chlorocyclopentane
Br
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Br
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Chapter 12
Alkanes
12.6 Physical Properties of Alkanes and Cycloalkanes 12.7 Chemical Properties of Alkanes and Cycloalkanes
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Uses of Alkanes
Crude Oil
Methane, ethane, propane, and butane are gases at room temperature and used as fuels. Alkanes with 5-17 carbon atoms are liquids and found in gasoline, diesel, and jet fuels. Alkanes with 18 or more carbon atoms are solids and found in the waxy coatings of fruits and vegetables.
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The differences in boiling points are used to separate hydrocarbons in crude oil. Heating to higher temperatures produces gases that are removed and cooled.
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Combustion
A fuel such as propane reacts with oxygen and burns, producing CO2 and H2O. Propane is burned to obtain energy and heat for cooking or warming a room. 3CO2 + 4H2O C3H8 + 5O2
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Alkanes are typically not very reactive due to strong C-C single bonds. The most typical reaction is combustion, where an alkane reacts with oxygen to produce carbon dioxide, water, and energy. alkane + O2 CO2 + H2O + energy
Learning Check
Complete and balance the reaction for the complete combustion of C7H16.
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Solution
Step 1 C7H16 + O2 Step 2 and 3 C7H16 + O2 Step 4 C7H16 + 11O2 7CO2 + 8H2O
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Learning Check
CO2 + H2O Write the combustion reaction for ethane and balance.
7CO2 + 8H2O
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Solution
Write the combustion reaction for ethane and balance. ethane CH3CH3 = C2H6 C2H6 + 7/2 O2 2CO2 + 3H2O Multiply through by 2 to clear 7/2 2C2H6 + 7O2 4CO2 + 6H2O
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Learning Check
Give the structures and names of the monosubstituted products for the reaction of propane with bromine in the presence of light.
Solution
Give the structures and names of the monosubstituted products for the reaction of propane with bromine in the presence of light. CH3CH2CH2 Br 1-bromopropane; propyl bromide Br | CH3CHCH3 2-bromopropane; isopropyl bromide
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