ch 11 Organic Compounds: Alkanes and Their Properties

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92 Terms

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Organic chemistry

Study of carbon-containing compounds

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Inorganic chemistry

Study of the elements and all noncarbon compounds

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Inorganic compound

Characterized by the presence of ionic bonding

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Covalent bonding

Bonding within molecules in organic compounds

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Ionic bonding

Bonding within molecules in inorganic compounds

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Flammability of organic compounds

Usually flammable

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Flammability of inorganic compounds

Usually non-flammable

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Normal physical state of organic compounds

Gases, liquids, or low-melting-point solids

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Normal physical state of inorganic compounds

Usually high-melting-point solids

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Conductivity of organic compounds

Non-conductor

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Conductivity of inorganic compounds

Conductor

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Rate of chemical reactions in organic compounds

Usually slow

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Rate of chemical reactions in inorganic compounds

Usually fast

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sp3 hybrid orbitals

Orbital produced from the combination of two or more nonequivalent orbitals of an atom

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Shape of sp3 orbital

Two-lobed shape, similar to the shape of a p orbital but with different-sized lobes

<p>Two-lobed shape, similar to the shape of a p orbital but with different-sized lobes</p>
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Sigma (σ) bond

Created by sharing of two electrons in the overlap region of a C (sp3) and an H (1s) orbital

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Tetrahedral configuration

Resultant shape when carbon is joined to four substituents (i.e., CH4)

<p>Resultant shape when carbon is joined to four substituents (i.e., CH4)</p>
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Isomers

Compounds that have the same molecular formula but different structural formulas

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Condensed structural formulas

A way to represent the structure of a compound in a simplified form

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Expanded structural formulas

A detailed representation of the structure of a compound showing all bonds

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IUPAC naming

Systematic method for naming organic chemical compounds

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Geometric isomers

Isomers that have the same molecular formula but differ in the spatial arrangement of atoms

<p>Isomers that have the same molecular formula but differ in the spatial arrangement of atoms</p>
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Carbon bonding

Carbon can bond to other carbon atoms.

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Covalent bonding limit

There is no limit to the number of carbon atoms that can bond covalently.

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Multiple bonds

May share more than one pair of electrons to form multiple bonds.

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Organic molecules

Organic molecules range from simple molecules like methane (CH4) to very complicated molecules containing over a million carbon atoms.

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Isomerism

Property in which two or more compounds have the same molecular formula but different arrangements of atoms.

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Structural isomer

Isomerism in which the atoms bond in different patterns.

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Example of structural isomer

Isomers of C2H6O.

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Ethyl alcohol

Ethyl alcohol is a liquid at room temperature and completely soluble in water.

<p>Ethyl alcohol is a liquid at room temperature and completely soluble in water.</p>
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Dimethyl ether

Dimethyl ether is a gas at room temperature and only partially soluble in water.

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Functional group

Unique reactive combinations of atoms that differentiate molecules of organic compounds of one class from those of another.

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Functional group characteristics

Except for alkanes, each functional group contains a multiple bond or at least one oxygen or nitrogen atom.

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Expanded structural formula

Shows all the covalent bonds.

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Condensed structural formula

Shows the general arrangement of atoms but without showing all the covalent bonds.

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Example of condensed structural formula

CH3CH2CH2CH3 or CH3(CH2)2CH3.

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Hydrocarbon

Organic compound that contains only carbon and hydrogen.

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Hydrocarbon properties

Helps to understand the chemical properties of more complex biomolecules.

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Hydrocarbon uses

Used as a primary source of energy and as an important source of raw materials for the manufacture of plastics, synthetic fibers, drugs, and other compounds used daily.

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Alkanes general formula

Represented by the general formula CnH2n+2.

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n in alkanes

n - Number of carbon atoms in the molecule.

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Methane

Methane (CH4) is the simplest alkane, which is the primary compound in natural gas.

<p>Methane (CH4) is the simplest alkane, which is the primary compound in natural gas.</p>
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Ethane

Ethane (C2H6) is a minor component of natural gas.

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Propane

Propane (C3H8) is used as an industrial fuel and for heating homes.

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Normal alkane

All carbon atoms are aligned in a continuous chain.

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Branched alkane

At least one carbon atom is not a part of a continuous chain.

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Normal vs Branched molecule

Branched molecule will have at least one carbon atom bonded to three or more other carbon atoms; normal molecule will not have any carbon atoms bonded to more than two other carbon atoms.

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C6H14 isomers

C6H14 has 5 possible structural isomers.

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Conformations

Different arrangements of atoms in space achieved by rotation about single bonds.

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Structural Isomers

Different conformations do not represent different structural isomers.

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IUPAC

International Union of Pure and Applied Chemistry.

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Methane

1 carbon atom, molecular formula CH4.

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Ethane

2 carbon atoms, molecular formula C2H6.

<p>2 carbon atoms, molecular formula C2H6.</p>
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Propane

3 carbon atoms, molecular formula C3H8.

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Butane

4 carbon atoms, molecular formula C4H10.

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Pentane

5 carbon atoms, molecular formula C5H12.

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Hexane

6 carbon atoms, molecular formula C6H14.

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Heptane

7 carbon atoms, molecular formula C7H16.

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Octane

8 carbon atoms, molecular formula C8H18.

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Nonane

9 carbon atoms, molecular formula C9H20.

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Decane

10 carbon atoms, molecular formula C10H22.

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Alkane Nomenclature Step 1

Identify and name the longest carbon chain.

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Alkane Nomenclature Step 2

Number the longest carbon chain to give the lowest number to any carbon to which a group is attached.

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Alkane Nomenclature Step 3

Locate and name the attached alkyl groups.

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Alkane Nomenclature Step 4

Combine the longest chain and the branches into the name.

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Alkane Nomenclature Step 5

For multiple branches, show the location of each branch with numbers.

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4-isopropyl-2,3-dimethylheptane

An example of a complex alkane name following IUPAC rules.

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di-, tri-, sec-, and t- prefixes

Can be ignored when listing multiple branches alphabetically.

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2,2,4-trimethylpentane

A branched-chain alkane with the molecular formula C8H18.

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3-isopropylhexane

An alkane with a six-carbon chain and an isopropyl group attached to the third carbon.

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3-ethyl-2,4-dimethylheptane

An alkane with a seven-carbon chain, an ethyl group on the third carbon, and two methyl groups on the second and fourth carbons.

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Cycloalkanes

Alkanes in which carbon atoms form rings.

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Cyclo-

Prefix used before the alkane name to indicate a ring structure.

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Substituted cycloalkanes

Cycloalkanes that have one or more groups attached to the ring.

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Geometric isomers

Molecules with restricted rotation around C—C bonds that differ in the three-dimensional arrangements of their atoms.

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Cis-

Isomers with substituents on the same side of a double bond or ring.

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Trans-

Isomers with substituents on opposite sides of a double bond or ring.

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Hydrophobic

Molecules or parts of molecules that are insoluble in water.

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Homologous series

Group of compounds with the same functional class that differ by a —CH2— group.

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Physical properties of alkanes

Odorless compounds that are non-polar with weak intermolecular forces.

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Methane

The simplest alkane with the formula CH4, melting point -182.5°C and boiling point -164.0°C.

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Ethane

An alkane with the formula CH3CH3, melting point -183.2°C and boiling point -88.6°C.

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Propane

An alkane with the formula CH3CH2CH3, melting point -189.7°C and boiling point -42.1°C.

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Butane

An alkane with the formula CH3CH2CH2CH3, melting point -133.4°C and boiling point -0.5°C.

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Pentane

An alkane with the formula CH3CH2CH2CH2CH3, melting point -129.7°C and boiling point 36.1°C.

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Hexane

An alkane with the formula CH3CH2CH2CH2CH2CH3, melting point -95.3°C and boiling point 68.9°C.

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Heptane

An alkane with the formula CH3CH2CH2CH2CH2CH2CH3, melting point -90.6°C and boiling point 98.4°C.

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Octane

An alkane with the formula CH3CH2CH2CH2CH2CH2CH2CH3, melting point -56.8°C and boiling point 125.7°C.

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Nonane

An alkane with the formula CH3CH2CH2CH2CH2CH2CH2CH2CH3, melting point -53.5°C and boiling point 150.8°C.

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Decane

An alkane with the formula CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3, melting point -29.7°C and boiling point 174.1°C.

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Combustion

A significant reaction of alkanes involving rapid oxidation, producing CO2 and H2O.

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Incomplete combustion

A reaction that occurs when there is not enough oxygen available, producing CO and H2O.