Title Alkanes and alkenes Data Collection, Data Processing and Presentation Alkanes I. Physical properties A. Volatility 1.

The boiling points of methane and hexane1 are: Substance Methane (CH4) Hexane (C6H14)

Boiling point (oC) - 161.6 68.7

2. The first straight-chain alkane to be liquid at room temperature and pressure is pentane (C5H12). This is because the melting point and the boiling point2 for pentane are 129.8 oC and 36.1 oC respectively where the room temperature3 (25 C) is laid between both points. 3. Alcohol that has a boiling point closest to that hexane is methanol, CH3OH4, (64.7 oC). Hexane is the 6th compound for alkanes and methanol is the 1st compound for alcohols and because of the presence of hydrogen bond between the molecules in methanol, more heat is required in order to break the bond as hydrogen bond is stronger compared to Van der Waals force. Even though hexanes intermolecular force for hexane is Van der Waals forces, the existence of six carbon chain in its molecules causes hexane to have nearly equal boiling point with methanol. Thus, because of these properties, methanol has the closest boiling point to hexane. B. Solubility Method 2 3 cm3 of hexane was put and water was added twice volume of hexane. It was shaken and stood in a rack. Observation Two layers of colourless solution were produced with colourless hexane on the top of water.

1. No. Hexane does not dissolve in water. The reason why the two liquids behave this way is hexane is a non-polar molecule which would only dissolve in the non-polar solvent. On the other hand, water is a polar solvent. Thus, hexane can not dissolve in water as it can not form hydrogen bond with water molecules. 2. Hexane is less dense than water, with density 0.66 g cm-3 and 1.00 g cm-3 respectively. Because of this property, hexane is formed on top of water in the test tube.
1

Raymond Chang. Chemistry, Seventh Edition. New York: The McGraw-Hill Companies, Inc., 2002. (p. 950) 2 Ibid. 3 Chemistry. Microsoft Encarta Encyclopedia Deluxe 2004. Version 13.0.0.0531. Redmond, USA. 4 Methanol. Microsoft Encarta Encyclopedia Deluxe 2004. Version 13.0.0.0531. Redmond, USA.

3. As their relative molecular masses (RMM) increase, the densities of straightchain alkanes also increase. This happens because of the increasing strength of intramolecular forces for each straight-chain alkanes as their masses increase which resulting in the formation of more condensed compound. II. Chemical properties A. Action of some common reagents on hexane Reagent Solubility in water Bromine water Slightly soluble

Potassium manganate (VII) solution Not soluble Sodium hydroxide solution Concentrated sulphuric acid

Observation Two layers of solution was formed; a colourless hexane solution on top of the brown bromine water. Two layers of solution was formed; a colourless hexane solution on top of the purple potassium manganate (VII) solution. Two layers of colourless solution were formed with hexane solution on top of each solution.

1. No. Hexane does not react with any of above substance under normal laboratory conditions because hexane is classified as a saturated organic compound where no alteration can be done to its structure. 2. Bromine is more soluble in hexane compared to water as it only slightly soluble in water. The reason is because both of the compounds, bromine and hexane, are non-polar molecules and their intermolecular forces, Van der Waals forces allow both compounds to dissolve in each other. While in water, bromine is slightly soluble as it can not form hydrogen bond with water molecules. 3. Potassium manganate (VII) is more soluble in water compared to hexane. The reason is because both of the compounds, potassium manganate (VII) solution and water are polar molecules and their intermolecular forces; hydrogen bonds allow both compounds to dissolve in each other. On the other hand, hexane is a non-polar compound which only would react with other non-polar compound because of the intermolecular bond. B. Reaction of hexane with bromine Observation After 10 minutes exposure After blown with a little to light ammonia The original brown bromine White fumes are produced 1 (wrapped) solution remains inside the test tube. The original brown bromine No white fumes are 2 (non-wrapped) solution changes to produced inside the test colourless tube. *White fumes produced are ammonium bromide (NH4Br) Test tube (condition)

1. Hexane reacts with bromine in the presence of ultraviolet light which already exists in the sunlight. 2. In this reaction, two products are formed and one of the products is an inorganic compound. C6H14 (l) + Br2 (l) C6H13Br (l) + HBr (l) From above equation, the inorganic compound being produced is hydrogen bromide (HBr). 3. The structural formula for one of the organic compound is:

4. The reaction is called as substitution reaction5. In this reaction, an atom or group in a molecule is replaced by another atom to form a new molecule. C.Combustion of alkanes Test Method Two drops of hexane was put into a 1 crucible and a lighted splint was applied on it. A small piece of paraffin was put in 2 a crucible and a lighted splint was applied on it. Observation A big flame is produced and minimal amount of soot is released. Paraffin is melted by the lighted splint.

Test 1: 1. Balanced equation for the reaction is as below. 2C6H14 (l) + 19O2 (g)

12CO2 (g) + 14H2O (l)

2. If the test tube is held upside down and lighted, an incomplete combustion will occur and more soot will be released. This is because of lack of oxygen in the test tube due to the presence of gaseous hexane. Test 2: 1. No. the wax can not be easily ignited. 2. Even though both wax and hexane are alkanes, wax is harder to ignite compared to hexane because wax contains a very long carbon chain which means it has a high relative molecular mass. Consequently, as its relative molecular mass increases the Van der Waals force also increases which causes more energy needed in order to ignite wax. However, hexane only consists of 6carbon chain which has low relative molecular mass. Thus, it can be easily ignited.
5

Michael Clugston and Rosalind Flemming. Advanced CHEMISTRY. New York: Oxford University Press, 2000. (p. 393)

3. A candle has a wick because it has special properties. A wick can be burned easily but can not be ignited easily. Thus, with these properties, it can decelerate the burning process of a candle. Alkenes I. Reactions of cyclohexene A. Burning Method 1 drop of cyclohexene was burned on a small tuft of ceramic wool in a crucible, flame was produced with some soot was released.

Observation Flame was produced with some soot was released.

1. Four products formed when the cyclohexene burned are carbon (C), carbon monoxide (CO), carbon dioxide (CO2) and water (H2O). 2. An equation for the complete combustion of cyclohexene (C6H10) in excess oxygen is as below. 2C6H10 (l) + 17O2 (g) B. Reaction with bromine Method 1 cm3 of bromine water was added to 3 drops of cyclohexene and was shaken.

12CO2 (g) + 10H2O (l)

Observation The brown bromine water is decolourized and a colourless solution is formed.

1. In this reaction, the bromine molecules are polarized and formed a positive bromine ion and a negative bromine ion per bromine molecule. The positive ion attacks the high electron density region in cyclohexene which is the double bond and forms a carbon cation that will be bonded to the negative ion. C6H10 (l) + Br2 (aq)

C6H10Br2 (l)

The product that has been produced is 1,2-dibromocyclohexene. C.Reaction with potassium manganate (VII) Method 1 cm3 of dilute sulphuric acid and 3 drops of potassium manganate (VII) were added to 3 drops of cyclohexene. It then was shaken. Observation The purple potassium manganate (VII) is decolourized and a colourless solution is formed.

1. In this reaction, cyclohexene undergoes addition process of two hydroxyl group which are originated from potassium manganate (VII) solution to form a colourless solution, cyclohexane-1,2-diol.

D.Reaction with concentrated sulphuric acid Method 3 drops of concentrated sulphuric acid was added to 3 drops of cyclohexene.

Observation The colourless mixture changed to a yellow solution and heat was released.

1. In this reaction, concentrated sulphuric acid (H-OSO2OH) is used as a catalyst. In the first step, cyclohexene is reacted with concentrated sulphuric acid to H produce cyclohexyl hydrogensulphate. C6H10 + H-OSO2OH

OSO2OH

Then, water is added to cyclohexyl hydrogensulphate to produce cyclohexanol and reconstruct the catalyst sulphuric acid. H OSO2OH + H2O

OH

+ H2SO4

2. Addition reaction is a reaction where two molecules are added together to form one larger molecule. In this reaction, a new molecule is produced from other two compounds. 3. Alkenes readily undergo addition reaction because it is classified as unsaturated compound because it consists of double bond. This double bond is built by a sigma bond and a pi bond. Compared to sigma bond, pi bond is easily broken and this is the reason for alkenes reactivity.