Chemistry 201 C Organic Compounds: Alkanes and Cycloalkanes

This presentation was created by Professor Carl H. Snyder Chemistry Department University of Miami Coral Gables, FL 33124 CSnyder@miami.edu Copyright 2004 by Carl H. Snyder, University of Miami. All rights reserved.

Lewis Structures
Lewis structures of the hydrogen atom and the carbon atom. Lewis structures show the elemental symbol and the valence electrons.

The Lewis Structure of Methane

Methane consists of 4 hydrogens covalently bonded to one central carbon atom.

Methane, A Covalent Hydrocarbon

Methane - The Molecular Model

Methane in 3-dimensional perspective.

Methane in a 2-dimensional representation.

The Methyl Radical

A Radical

methyl radical Loss of a hydrogen atom from methane produces the methyl radical, also known as the methyl free radical. Note that loss of any one of methanes four hydrogens produces the same methyl radical.

In chemistry, a radical is any species bearing an unpaired electron.

Ethane From Two Methyl Radicals

The combination of two methyl radicals forms ethane. Ethane can form in many other ways as well.

Ethane - Expanded Structure, Condensed Structure, And Molecular Formula

Expanded structure

Condensed structure Molecular formula

Ethane - The Molecular Model

The Ethyl Radical

Ethane in 3-dimensional perspective. the ethyl radical Ethane in a 2-dimensional representation. Loss of a hydrogen atom from ethane produces the ethyl radical, also known as the ethyl free radical. Notice that loss of any one of ethanes six hydrogens produces the same ethyl radical.

Propane From An Ethyl Radical And A Methyl Radical

Propane - Expanded Structure, Condensed Structure, And Molecular Formula

Expanded structure

The combination of an ethyl radical and a methyl radical produces propane. Propane can form in many other ways as well.

Condensed structure Molecular formula

Propane - The Molecular Model

Alkanes and Alkyl Groups

Methane, ethane, and propane are members of a group of hydrocarbons known as the alkanes. Removing a hydrogen atom from an alkane produces an alkyl group. CH3- is the methyl group, as in methyl chloride, CH3-Cl ; CH3-CH2- is the ethyl group, as in ethyl chloride, CH3-CH2-Cl Alkyl groups are indicated generically by the symbol R-, as in R-Cl

Propane in 3-dimensional perspective.

Propane, a 2-dimensional representation.

The First Members of The Alkane Series

Some Terms to Remember

Hydrocarbon - A compound composed exclusively of hydrogen and carbon. Saturated hydrocarbon - A compound of general formula CnH(2n+2) containing the maximum possible number of hydrogens per carbon. Alkane - The family of compounds with the general formula CnH(2n+2); the saturated hydrocarbons. Aliphatic hydrocarbons - An older term for the alkane family, derived from a Greek word for "fat" or "fatty substance"

All compounds whose molecular formulas fit the general formula CnH(2n+2) are alkanes

Classes of Carbons Primary (1o) and Secondary (2o) Carbons A primary (1o)
carbon is bonded to exactly one other carbon. A secondary (2o) carbon is bonded to exactly two other carbons

Classes of Hydrogens
Hydrogens always take the same class as the carbons to which they are bonded. All hydrogens on a primary carbon are primary hydrogens. All hydrogens on a secondary carbon are secondary hydrogens.

1o

And

2o

Hydrogens In Propane
1 - 1o carbon

1o And 2o Hydrogens In Propane

1 - 1o carbon 1 - 1o carbon

1 - 1o carbon

3 - 1o hydrogens Propane contains two 1o carbons and . . .

3 - 1o hydrogens

Propane contains two 1o carbons and six 1o hydrogens, and . . .

1o And 2o Hydrogens In Propane

1 - 1o carbon 1 - 1o carbon 1 - 2o carbon

1o And 2o Hydrogens In Propane

1 - 1o carbon 1 - 1o carbon 1 - 2o carbon

2 - 2o hydrogens 3 - 1o hydrogens 3 - 1o hydrogens 1o carbons and six 3 - 1o hydrogens 3 - 1o hydrogens

Propane contains two 1o hydrogens, and one 2o carbon and . . .

Propane contains two 1o carbons and six 1o hydrogens, and one 2o carbon and two 2 o hydrogens.

Two Different Propyl Radicals

Two Different Propyl Radicals

primary propyl radical

primary propyl radical

secondary propyl radical Removing a 1o H produces a 1o propyl radical. Removing a 1o H produces a 1o propyl radical. Removing a 2o H produces a 2o propyl radical.

The Propyl Radical and the Isopropyl Radical

Two Different Butanes

The addition of a methyl group to the 1o carbon of a propyl radical produces a straight-chain C4H10.

Two Different Butanes

Isomers
Different compounds that share the same molecular formula are known as isomers. The straight-chain structure and the branchedchain structure represent the two isomers of butane, C4H10.

The addition of a methyl group to the 1o carbon of a propyl radical produces a straight-chain C4H10. The addition of a methyl group to the 2o carbon of an isopropyl radical produces a branched-chain C4H10.

The Two Isomers of Butane

The Tertiary Carbon And The Tertiary Hydrogen Of Isobutane

A tertiary (3o) carbon is bonded to exactly three other carbons. The hydrogen on the tertiary carbon is a tertiary hydrogen.

Although each structure represents one of the isomers of butane, C4H10, the straight-chain structure is known as butane, and the branched-chain structure is known as isobutane.

The Tertiary Carbon And The Tertiary Hydrogen Of Isobutane

A tertiary (3o) carbon is bonded to exactly three other carbons. The hydrogen on the tertiary carbon is a tertiary hydrogen. 3o carbon

The Tertiary Carbon And The Tertiary Hydrogen Of Isobutane

A tertiary (3o) carbon is bonded to exactly three other carbons. The hydrogen on the tertiary carbon is a tertiary hydrogen. 3o carbon
3 H

Theyre All Butane, C4H10

The Three Isomers of Pentane, C5H12

Each of these structures represents butane, the straight-chain, unbranched isomer. As long as you can pass from one end of the chain to the other end without encountering a branch, its butane.

pentane
pentane Pentane

isopentane
isopentane Isopentane neopentane Neopentane

A quaternary (4o) carbon is bonded to exactly four other carbons. Because all of its valences are consumed in bonding to other carbons, a quaternary carbon cannot be bonded to a hydrogen. Quaternary hydrogens do not exist.

The Quaternary Carbon of Neopentane

quaternary carbon

quaternary carbon

The First 10 Alkanes

We are concerned with the names of the first 10 alkanes. Those with five or more carbons begin with terms derived from Latin or Greek words for the numbers one through ten. They end with -ane to specify that we are dealing with alkanes.

Alkyl Groups: The Two C3 Alkyl Groups

The Four C4 Alkyl Groups

CH3-CH2-CH2-Cl is propyl chloride CH3-CH-CH3 is isopropyl chloride | Cl

CH3-CH2-CH2-CH2-Cl is butyl chloride CH3-CH2-CH-CH3 is sec-butyl chloride | Cl

The Four C4 Alkyl Groups

The Four C4 Alkyl Groups

CH3-CH-CH2-Cl is isobutyl chloride | CH3

CH3 | CH3-C-Cl is tert-butyl chloride | CH3

The enormous number of isomers of alkanes and alkyl groups overwhelms systems that use prefixes such as iso- and neo-. The IUPAC system can accommodate large numbers of isomers.

Alkane Isomers

The IUPAC (International Union of Pure and Applied Chemistry) System

IUPAC

IUPAC

IUPAC

IUPAC

IUPAC

IUPAC

IUPAC IUPAC

IUPAC

IUPAC Example #1

IUPAC Example #1

IUPAC Example #1

IUPAC Example #1

IUPAC Example #2

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IUPAC Example #2

IUPAC Example #2

IUPAC Example #2

IUPAC Example #3

IUPAC Example #3

IUPAC Example #3

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IUPAC Example #3

IUPAC Example #4

IUPAC Example #4

IUPAC Example #4

IUPAC Example #4 IUPAC Example #5

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IUPAC Example #5

IUPAC Example #5

IUPAC Example #5
CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2

Cycloalkanes

Naming Cycloalkanes

Naming Cycloalkanes

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Naming Cycloalkanes

Naming Cycloalkanes

Cycloalkanes - Example #1

Cycloalkanes - Example #1

Cycloalkanes - Example #1

Cycloalkanes - Example #1

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Cycloalkanes - Example #2

Cycloalkanes - Example #2

Cycloalkanes - Example #2

Cycloalkanes - Example #3

Cycloalkanes - Example #3

Cycloalkanes - Example #3

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Kinds of Isomerism Cycloalkanes - Example #3

Constitutional isomers show different sequences in the connections of their atoms - butane and isobutane are constitutional isomers. Stereoisomers show the same sequences of connections, but differ in the 3-dimensional, spacial orientation of their atoms.

The Rigid Ring of Cyclopropane

The rigid ring of cyclopropane fixes substituents on each side of the ring, allowing the kind of stereoisomerism known as geometric or cis/trans isomerism.

cis-1,2-Dimethylcyclopropane

The two CH3 groups of cis-1,2dimethylcyclopropane lie on the same side of the ring. Moving one of the CH3 groups to the other side of the ring would require breaking covalent bonds, which is a high-energy process.

trans-1,2Dimethylcyclopropane

Configurational Isomers
If interconverting isomers (as in the case of stereoisomers) requires the breaking and reforming of covalent bonds, the isomers are known as configurational isomers.

The two CH3 groups of trans-1,2dimethylcyclopropane lie on opposite sides of the ring. Moving one of the CH3 groups to the other side of the ring would require breaking covalent bonds, which is a high-energy process.

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End
Organic Compounds: Alkanes and Cycloalkanes

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