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Alkanes Alk
general formula CnH2n+2 alkanes are saturated (each C is bound to 4 other atoms)
Alkanes
Hydrocarbon chains where all the bonds between carbons are SINGLE b d b t b bonds Name uses the ending ane Examples: Methane, Propane, Butane, Octane, Methane, Propane, Butane, Octane, 2-methylpentane methylpentane
Endings
Alkanes (all C-C single bonded parent chain) Cend in ane Methane CH4 Methane Ethane C2H6 Ethane Propane C3H8 Propane Attached carbon groups (substituents) end i yl Att h d b (substituents) d in l b tit t Methyl CH3 Methyl Ethyl CH3CH2Ethyl l Propyl CH3CH2CH2 Propyl
3-ethylpentane
1 8
27 3 6 4 5 5 4 7 2 6 3 8 1 1 7 2 6 3 5 4 4 5 3 6 72 1
Groups on 2 and 5
Groups on 3 and 6
Step 5. Alphabetize the groups, combine lik groups, and assemble. bi like d bl
The prefixes di, tri, tetra di, etc., used to designate several groups of the same kind ki d Prefixes are not considered when alphabetizing (Example: dimethyl = m for alphabetizing) Parent chain goes LAST
1,1,1-trichloro-1fluoromethane
1,1-dichloro-1,1difluoromethane
Order of Priority
IN A TIE halogens get the lower number TIE, before alkyl groups
Order of Priority
IN A TIE between SIMILAR GROUPS the GROUPS, group lower ALPHABETICALLY gets the lower number
Isomers
St i ht chain alkanes: A alkane Straight h i alkanes: An lk lk that has all its carbons connected in a row. row. Branched chain alkanes: An alkane alkanes: that has a branching connection of carbons. carbons. Isomers: Compounds with same Isomers: molecular formula but different structures. structures.
There is only one possible way that the carbons in methane (CH4), ethane (C2H6), arranged. and propane (C3H8) can be arranged.
However, However carbons in butane (C4H10) can be arranged in two ways; four carbons in a row ways; (linear alkane) or a branching (branched alkane) alkane) alkane). These two structures are two isomers for butane. butane.
Isomers
methane 1 isomer
ethane 1 isomer
propane 1 isomer
Isomers
isobutane
Different isomers are completely different compounds. compounds. They have different structures, different physical properties such as melting p y p p g point and boiling point, and may have different physiological properties. properties.
Learning Check
Draw all possible structural isomers of C5H12
H C C H H
H C C C H
H C C C C
Alkanes
Example: Name the following compounds:
Structural Formulas
Alkanes are written with structural formulas that are Expanded to show each bond bond. Condensed to show each carbon atom and its attached hydrogen atoms atoms. Line to show bonds as lines and omit hydrogens
H H C H H C H H C H H H3C H2 C CH3
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Alkanes
Example: Write the condensed structure for the following compounds: t t f th f ll i d 3,33,3-dimethylpentane 2-methyl-4-sec-butyloctane methyl- sec-bu y oc a e e y 1,2-dichloro1,2-dichloro-3-methylheptane
Cycloalkanes
Are cyclic alkanes alkanes. Have 2H fewer than the open chain. Are named by using the prefix cyclo before cyclothe name of the alkane chain with the same number of carbon atoms.
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Cycloalkanes
The structural formulas of cycloalkanes are usually y y represented by geometric figures, Cyclopropane CH2 Cyclobutane CH2 CH2 CH2 CH2 CH2 CH2
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Cycloalkanes
cyclopropane
Cycloalkanes
cyclobutane
cyclopentane
cyclohexane
Cycloalkanes
Nomenclature of Cycloalkanes
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Crude Oil
The hydrocarbons in crude oil are Separated by boiling points. Heated to higher temperatures to produce prod ce gases that can be removed and cooled.
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Alkane Reactions
1. Combustion
The Th combustion of carbon compounds, especially h d b ti f b d i ll hydrocarbons, h b b has been th the most important source of heat energy for human civilizations throughout recorded history.
CH3-CH2-CH3 + 5 O2 > 3 CO2 + 4 H2O + heat Two points concerning this reaction are important: 1. Since all the covalent bonds in the reactant molecules are broken, the quantity of heat evolved in this reaction is related to the strength of these bonds (and of course, the strength of the bonds formed in (and, course the products). 2. The stoichiometry of the reactants is important. If insufficient oxygen pp products will consist of carbon monoxide, a , is supplied some of the p highly toxic gas.
Combustion of Alkanes
Alkanes Undergo combustion by reacting with oxygen to p produce carbon dioxide, , water, and energy. Are typically not very reactive d t strong Cti due to t C C single bonds.
Copyright 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings
alkane + O2
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2. Halogenation
Halogenation is the replacement of one or more hydrogen atoms in an organic compound by a halogen ( g p y g (fluorine, chlorine, bromine or , , iodine).
CH4 + Cl2 + energy > CH3Cl + HCl When alkanes react with halogens: One or more hydrogens will be replaced with halogens y g p g Halogens prefer to go to the more substituted (location with more surrounding carbons) location Tertiary is more reactive than secondary which is more reactive than primary Light or heat is required to form the radicals Radicals have unpaired electrons and violate the octet rule (reactive)
+ X
R R
+ X
X
+ X
X
+ X
+ X
used to indicate an unpaired electron (free radical) X = shorthand for a halogen atom R = shorthand for an organic compound or group
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2. propagation
3. termination;
tertiary
secondary
primary
methyl
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+ Cl2
+ Br2
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+ Cl2
C H
+ HCl
+ Br2
CH2 H2 C
+ HBr
+ Br2
Br
+ HBr
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