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 * Alkanes (CnHn+2) **

 1 methane  2 ethane 3 propane 4 butane  5 pentane  6 hexane  7 heptane 8 octane  9 nonane  10 decane

// Rules to Naming //

 1. Name is dependent on the number of carbons.  2. Determine the parent chain ( this is the longest possible chain of uninterupted carbons molecules.)  3. Determine the side chain and name it according to the number of carbon atoms on the side chain.  4. Determine the carbon on which the side chain is attached. assign the lest number to it. <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;"> - separate number and letter with a - <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;"> - separate number and number with a , <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;"> 5. If there is more than one of the same type of side chain, use a prefix ( mono, bi, tri...) <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;"> 6. priority is given to the bulky group <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;"> 7. Diferent side chains should be written in alphabetical order.

|| || || || || || || || || || ||
 * =<span style="background-attachment: initial; background-clip: initial; background-color: #63c6de; background-image: initial; background-origin: initial; background-position: initial initial; background-repeat: initial initial; color: #ffff9c; font: normal normal bold 12pt/normal verdana; text-decoration: none;">ummary of the Properties and Uses of Hydrocarbons = ||
 * ||~ //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">Name // ||~ //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">Molecular Formula // ||~ //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">Molecular Mass // ||~ //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">Melting Point (oC) // ||~ //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">Boiling Point (oC) // ||~ //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">State (25oC, 101.3kPa) // ||~ //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">Density (liquid g cm-3, 20oC) // ||~ //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">Flashpoint (oC) // ||~ //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">Enthalpy of Combustion (kJ mol-1) // ||~ //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">Uses // ||
 * methane || CH4 || 16 || -182 || -162 || gas ||  ||   || -889 || //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">major component of natural gas (fuel) // ||
 * ethane || C2H6 || 30 || -183 || -88.6 || gas ||  ||   || <-1557 || //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">component of natural gas (fuel) // ||
 * propane || C3H8 || 44 || -188 || -42.1 || gas ||  ||   || -2217 || //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">component of liquefied petroleum gas (LPG), bottled gas (fuel) // ||
 * butane || C4H10 || 58 || -138 || -0.5 || gas ||  ||   || -2874 || //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">component of liquefied petroleum gas (LPG), cigarette lighters (fuel) // ||
 * pentane || C5H12 || 72 || -130 || 36.1 || liquid || 0.626 || -49 || -3536 || //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">component of petrol (fuel) // ||
 * hexane || C6H14 || 86 || -95.3 || 68.7 || liquid || 0.659 || -22 || -4190 || //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">component of petrol (fuel) // ||
 * heptane || C7H16 || 100 || -90.6 || 98.4 || liquid ||  || -4 || -4847 || //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">component of petrol (fuel) // ||
 * octane || C8H18 || 114 || -56.8 || 126 || liquid ||  ||   || -5506 || //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">major component of petrol (fuel) // ||
 * nonane || C9H20 || 128 ||  ||   ||   ||   ||   ||   || //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">component of petrol (fuel) // ||
 * decane || C10H22 || 142 || -30 || 174 || liquid || 0.730 ||  ||   || //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">component of petrol (fuel) // ||
 * hexadecane || C16H34 || 226 || 18.5 || 288 || liquid || 0.775 ||  ||   || //<span style="color: navy; font: italic normal normal 8pt/normal verdana;">component of diesel fuel & heating oil // ||
 * eicosane || C20H42 || 282 || 36 || 343 || solid ||  ||   ||   ||   ||

<span style="color: #63c6de; font: normal normal bold 10pt/normal verdana; text-decoration: none;">Trends
> (propane and butane are easily condensed under pressure & are commonly sold as liquids) > alkanes containing 5 carbons up to about 19 are colourless liquids > (petrol & kerosene are mixtures of liquid alkanes, dye is added to the fluids for safety reasons) > alkanes with more than about 20 carbon atoms are colourless, waxy solids > (paraffin wax is a mixture of solid alkanes) > > > > (Van der Waal's Forces/London Forces/Dispersion Forces/Weak Intermolecular Forces) > Melting and Boiling Points increase as the molecular mass increases > > > (will undergo <span style="border-bottom-color: #63c6de; border-bottom-style: solid; border-bottom-width: 1px; color: #31b5d6; font-size: 40pt; font: normal normal normal 10pt/normal verdana; text-decoration: none;">[|halogenation] by substitution reaction in the presence of ultra-violet light) >
 * Alkanes are colourlessmethane to butane are colourless gases
 * Alkanes are less <span style="border-bottom-color: #63c6de; border-bottom-style: solid; border-bottom-width: 1px; color: #31b5d6; font-size: 40pt; font: normal normal normal 10pt/normal verdana; text-decoration: none;">[|dense] than water (alkanes will float on top of water)density increases with increasing molecular mass
 * Simple alkanes have low melting and boiling points.Alkanes are <span style="border-bottom-color: #63c6de; border-bottom-style: solid; border-bottom-width: 1px; color: #31b5d6; font-size: 40pt; font: normal normal normal 10pt/normal verdana; text-decoration: none;">[|non-polar] so only weak <span style="border-bottom-color: #63c6de; border-bottom-style: solid; border-bottom-width: 1px; color: #31b5d6; font-size: 40pt; font: normal normal normal 10pt/normal verdana; text-decoration: none;">[|intermolecular forces] act between the alkane molecules
 * Alkanes are insoluble in polar solvents like water
 * Alkanes are relatively unreactive(they will <span style="border-bottom-color: #63c6de; border-bottom-style: solid; border-bottom-width: 1px; color: #31b5d6; font-size: 40pt; font: normal normal normal 10pt/normal verdana; text-decoration: none;">[|combust] : commonly used as fuels since large amounts of energy are released, the longer the chain, the more bonds are broken, the greater the energy released)
 * Alkanes with *flashpoints below room temperature (the components of petrol for example) should be stored in strong metal containers with narrow mouths & tightly sealed lids to prevent the vapour from escaping & to prevent a naked flame or spark from igniting the vapour/air mixture.

From: http://www.ausetute.com.au/usehydrc.html


 * <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;">Alkenes (CnH2n) **

<span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;">1 methane <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;"> 2 ethene <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;"> 3 propene <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;"> 4 butene <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;">5 pentene <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;">6 hexene <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;">7 heptene <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;">8 octene <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;">9 nonene <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;">10 decene

<span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;">>>>>>>>ALWAYS REMEMBER TO FIND THE LONGEST POSSIBLE CHAIN!<<<<<<< <span style="color: #d500ff; font-family: 'Comic Sans MS',cursive;">(for alkenes, the longest possible chain should encompass the double bond)

Although the double bond between two carbon atoms is stronger link than a single bond, it is not twice as strong, (i.e. the second bond formed between the carbon atoms is weaker than the first). Thus, the second bond is more vulnerable to attack by suitable reagents, even under fairly mild conditions. Thus, the reaction of this second bond tend to be addition reactions, where the unsaturated carbon atoms become saturated. The alkenes are much more reactive than alkanes. **Combustion of Alkenes**The alkenes are highly flammable and burn readily in air, forming carbon dioxide and water,. For example, ethene burns as follows :

code **C2H4  +   3 O2   ==>   2 CO2   +   2 H2O**

code

**Addition Reactions across the Double Bond**Because the alkenes are unsaturated hydrocarbons, their most important reactions are addition reactions across the double bond. The alkenes are readily oxidised by potassium permanganate to form glycols. For example, ethene is oxidised to ethylene glycol.

code **3 H2C=CH2  +   2 KMnO4   +   4 H2O

==>    2MnO2  +  2KOH   +   CH2OHCH2OH

Ethylene Glycol**

code During the oxidation of alkenes, the purple colour of the permanganate solution disappears and the reaction constitutes a test, known as, to detect unsaturation in any compound.

**Addition of Hydrogen**The alkenes are readily reduced by the addition of hydrogen across the double bond to form alkanes (i.e. reduction of alkenes). For example, when an alkenes is passed over a nickel catalyst at 150 degC, the alkene is reduced to an alkane.

code **H2C=CH2  +   H2      ==>             CH3CH3

Ethene                             Ethane**

code

**Addition of Halogen**Halogens readily add across the double bond of the alkenes to form dihalides

code **H2C=CH2  +   Cl2       ==>     CH2Cl CH2Cl

Ethene                         DiChloroEthane**

code

**H2C=CH2 + Br2 ==> H2Br CH2Br** **Ethene DiBromoEthane** The decolourisation of bromine is a second test for an unsaturated organic compound.

**Addition of Hydrogen Halide**Hydrogen halides readily add across the double bond of the alkenes to form alkyl halides The reactivity of ethene, with the halogen acids is in the order

code **HI   >>    HBr    >    HCl**

code Thus, ethene reacts readily with hydrogen iodide and with hydrogen bromide at room temperature to form ethyl iodide and ethyl bromide, respectively.

code **H2C=CH2    +    HI      ==>        CH3CH2I

Ethyl Iodide**

code With ethene, the hydrogen atom of the halogen acids can add to either carbon atom to yield bromoethane.

However, with higher members of the ethene series, the orientation of the addition of asymmetric molecules across the double bond is governed by the [|Markownikoff Rule].

**Addition of Water**Water can add across the double bond of the alkenes to form aliphatic alcohols. This is hydration reaction is catalysed under a number of different conditions. When ethylene and steam are heated (i.e. at 300o Centigrade) under high pressure (i.e. at 70 atm.) in the presence of a catalyst (i.e. phosphoric acid,, on a silica support), ethanol is formed.

code **H2C=CH2  +   H2O       ==>     C2H5OH**

code

**Reaction with Sulphuric Acid**Similarly, fuming sulphuric acid absorbs ethylene at room temperature to form ethyl hydrogen sulphate, with much evolution of heat.

code **C2H4  +   H2SO4    ==>     C2H5.HSO4**

code If this is treated with water and warmed, ethanol is formed.

code **heat

C2H5.HSO4  +   H2O     ==>     C2H5OH + H2SO4**

code

**Polymerisation Reactions due to the Double Bond**When ethylene is heated under great pressure in the presence of a catalyst a large number of the molecules combine to form polythene, (C2H4)n, (i.e. Polyethylene). This particular kind of reaction is called an addition polymerisation and the mechanism by which it takes place is a reaction is a free radical chain reaction. The overall reaction is

code **n(C2H4)        ==>             (C2H4)n

Ethene                         Polythene**

code

The first three alkenes are gases, the intermediate alkenes are liquids and higher members of the olefin series are wax like solids at room temperature. The alkenes are insoluble in water, but are soluble in organic solvents. The liquids and solids have a density less than water. code
 * Compound   Formula    MP degC    BP degC    Density (g/ml)

==
=   =======    =======    ======== Ethylene    C2H4    -170    -102    0.6128 Propene       C3H6    -185    -47    0.6142 1-Butene   C4H8    -130    -6.5    0.6356**

code

There are two general methods for the preparation of alkenes. Both methods involve the dehydration of the appropriate aliphatic alcohol (i.e. the removal of a molecule of water from an alcohol). > The former method tends to be used in the laboratory preparation of alkenes, and the latter method is used in the industrial scale preparation of alkenes.
 * dehydration of the alcohol using concentrated sulphuric acid as the dehydrating agent, or
 * by passing the vapour of the alcohol over hot alumina.

The chemical bonding in alkenes can be illustrated by reference to the simplest alkene, ethene. This compound has the following structural

code **H      H

C = C

H      H**

code The double bond represents a four electron bond (i.e. two shared pairs of electrons). However, the two bond between the carbon atoms have significantly different chemical properties, and are formed in different ways. The first bond between the carbon atoms in ethene is a s bonds (sigma bonds) and is similar to the carbon to carbon bond found in the alkane series. However, the second bond between the carbon atoms in ethene is a p-bond (pi-bond), which is much more reactive than the sigma bond and behaves differently in a variety of experimental conditions. The ethene molecule is planar (i.e. all atoms lie in the same plane) and the bond angle between all the bonds (i.e. carbon to carbon and carbon to hydrogen) is 120 degrees. This observed structure for ethene can be explained in terms of sp2 hybridisation of the orbitals on the carbon atom. Thus, ethene is a flat molecule, the distance between the carbon atoms being less than that in ethene. Styrene, C6H5.CH=CH2, is the monomer used for the synthesis of the industrially important plastic, Polystyrene.

From: http://www.ucc.ie/academic/chem/dolchem/html/dict/alkenes.html

Alcohols and Ethers, Organic Derivatives of Water
[|Return] to the Organic Chemistry Page.

An alcohol is any compound with an OH group (alcohol group) attached to single bonded hydrocarbons (alkanes).
 * [[image:http://library.thinkquest.org/3659/orgchem/alcohol.gif align="center" caption="-OH"]]

alcohol group
||

alcohol general structure
|| The four most common alcohols are: code CH3OH

code

methanol (methyl alcohol)
|| code CH3CH2OH

code

ethanol (ethyl alcohol)
|| code CH3CH2CH2OH

code

1-propanol (propyl alcohol)
|| code OH  | CH3CHCH3

code

2-propanol (isopropyl alcohol)
|| Ethanol, when fermented from sugar, is the alcohol in beverages. It can also be made from ethene by the addition of water for nonbeverage use, like an additive to gassoline to make "gasahol." 2-Propanol (better known as isopropyl alcohol) is in (with some water) rubbing alcohol. It is also used in gasoline to prevent freezing of the gas line in automobiles by keeping excess moisture dissolved in the gasoline.

IUPAC Names of Alcohols
The parent chain of the alcohol must be the longest that includes the carbon holding the OH group. Give the -OH group the lower location number on the chain regardless of where alkyl substituents occur. Name the alkane attached to the OH group and replace the -e with an -ol. For example: code H                   | H H H-C-H H             | |   |   | H-C-C---C---C-H | |  |   |              H O   H   H                | H         Parent chain: butyl -OH group location: 2 Substituents locations: 3-methyl Alkane name: 3-methylbutane Alcohol name: 3-methyl-2-butanol

code

Ethers
Ethers are basically two alkyl groups joined to one oxygen. For example: Dimethyl ether was the "ether" once used as an anesthetic. The simple ethers above have very low boiling points because hydrogen bonds do not exist between neighboring molecules. Becuase of this, the boiling point of ethers are much lower than comparable alcohols. For example, 1-butanol boils at 117 °C, much higher than its isomer, diethyl ether, which boils at 34.5 °C.
 * ======dimethyl ether====== || ======diethyl ether====== || ======methyl ethyl ether====== || [[image:http://library.thinkquest.org/3659/orgchem/etherfamily.gif caption="R-O-R'"]]======ether general formula====== ||

Major Reactions of Alcohols and Ethers
Ethers act very much like alkanes. Like alkanes, they burn and are split apart when boiled in concentrated acids. But the alcohols have much reactivity.

Oxidation Reactions of Alcohols
To study the oxidation of alcohols, they must be subclassified into the following: code H | R-C-O-H | H

code

primary alcohol
|| code R' | R-C-O-H | H

code

secondary alcohol
|| code R' | R-C-O-H | R''

code

tertiary alcohol
|| Only primary and secondary alcohols are oxidized by oxidizing agents. When an alcohol is oxidized, an H attached to the alcohol carbon is removed as H-, and the H atom of the OH group leaves as H+. The two H become part of a water molecule with an O provided by the oxiding agent. Primary alcohols are oxidized to aldehydes. The net ionic equation for this when a dichromate ion is used as an oxidizing agent is: code 3RCH2OH + Cr2O72+ + 8H+ ==> 3RCH=O + 2Cr3+ + 7H2O

code For example, this is the oxidation of 1-propanol into propanal: code 3CH3CH2CH2OH + Cr2O72+ + 8H+ ==> 3CH3CH2CH=O + 2Cr3+ + 7H2O

code Since the boiling point of propanal is much lower than 1-propanol, it is boiled out of the solution as it forms. If it is not permitted to leave, it will further be oxidized into propanoic acid (CH3CH2COOH) since its tendency to be oxidized is greater than alcohol's. Secondary alcohols are oxidized to ketones. For example, the oxidation of 2-propanol gives propanone (more commonly called acetone): code CH3                      CH3 |                        | 3C-OH + Cr2O72- + 8H+ ==> 3C=O + 2Cr3+ + 7H2O |                        | CH3                       CH3

code Since ketones resist oxidation, they do not have to be removed as they form. Tertiary alcohols are not oxidized except by chain-breaking reactions, because they have no removable H atom on the alcohol carbon.

Dehydration Reactions of Alcohols
In a strong acid and heat, alcohols can undergo dehydration, losing a water molecule and levaing behind a carbon-carbon double bond. For example: code CH2-CH2 ==> CH2=CH2 + H2O H  OH ethanol     ethene  + water

code

code ==> + H2O cyclohexanol ==> cyclohexene + water

code Not only do chemists know it works, they also want to find out and know how it works. The examples above were elimination reactions. The thing that makes them possible is the proton-accepting ability of the oxygen atom of the OH group, and therefore, will react with concentrated strong acids. The following is the mechanism to how ethanol is changed into ethene using sulfuric acid as a catalyst: code CH2-CH2 + H2SO4 <==> CH2-CH2+ + HSO4- <==> CH2-CH2+ + H2O + HSO4- <==> CH2=CH2 + H2O + H2SO4 H  OH               H   O                 H                        / \ H  H
 * |               |   | <- (weak bond)  |

code

Substitution Reactions of Alcohols
In acidic conditions, the OH group of an alcohol can be replaced by a halogen atom. For example: code CH3CH2OH + HI ==> CH3CH2I + H2O ethanol + hydrogen iodide ==> iodoethane + water (ethyl iodide)

code

code + HCl ==> + H2O cyclohexanol + hydrogen chloride ==> chlorocyclohexane + water

code The mechanism for substitution reactions like the ones above are: code H+                / R-OH + H+ ==> R-O \                 H

code

Once the OH group has been protonated (added H+), the bond between the carbon and oxygen is weakened, allowing a halide ion to displace the H2O.

http://library.thinkquest.org/3659/orgchem/alcohol-ethers.html

For Aldehydes http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/aldket1.htm

For Carboxylic Acid http://www.tpub.com/content/armymedical/MD0803/MD08030101.htm

For Amines: http://www.huntsman.com/performance_products/Media/Amine_Applications_and_Properties_Data_2009.pdf