Topic 1- dot point 3

describe the dehydration of ethanol to ethylene and identify the need for a catalyst in this process and the catalyst used.

 The dehydration of ethanol is the chemical process whereby a water molecule is removed from ethanol, forming ethylene

 Dehydration of ethanol:
o ethanol ethylene + water
o C2H5OH (l) C2H4 (g) + H2O (l)
 An acid catalyst (concentrated sulfuric acid) is needed because the acid breaks the C–OH and C–H bonds, allowing the
formation of a double-bond and water (it also reduces the activation energy)
 Sulfuric acid is the chosen acid, because it is a powerful dehydrating agent

Describe the addition of water to ethylene resulting in the production of ethanol and identify the need for a catalyst in this
process and the catalyst used.
 The hydration of ethylene is the chemical process whereby a water molecule is added to ethylene, forming ethanol

 Hydration of ethylene:

o ethylene + water ethanol

o C2H4 (g) + H2O (l) C2H5OH (l)

 In this case, the acid catalyst (concentrated phosphoric acid) opens the double bond, allowing water to attach, forming
ethanol

Alcohols
 Functional group: hydroxyl (-OH)
 General formula: CnH2n+1OH
 Polar due to the OH group
 All are toxic to varying extents
 The greater the molar mass, the greater the molar heat of combustion.
 Some alkanols have isomers. (molecules with the same formula or elements in the same proportion but with different
arrangements.

Hexan-1-ol Hexan-2-ol

Prefix, # , # where OH
carbon atoms group is
describe and account for the many uses of ethanol as a solvent for polar and non-polar substances.
 Ethanol is able to act as a solvent for polar, non-polar and some ionic substances due to its unique molecular structure:

As can be seen, ethanol is not completely polar or completely non-polar:
o The OH- group: This section is polar, as a result, it can form polar bonds with other polar substances and dissolve
them
o The CH3CH2+ group: This section is non-polar, it can share dispersion forces with other non-polar substances and
dissolve them

 Hence, ethanol is used as a solvent in preparation of:

o Dyes/ food colourings
o Perfumes/aftershaves
o Pharmaceuticals

 Ethanol is an excellent solvent as it is miscible (soluble) not only in water but many other organic liquids.

outline the use of ethanol as a fuel and explain why it can be called a renewable resource.
 Combustion is the reaction whereby a hydrocarbon reacts with oxygen to form carbon dioxide and water vapour, releasing
energy (heat)
 Ethanol is able to undergo combustion, so it can be used as a fuel:
o C2H5OH (l) + 3O2 (g) 2CO2 (g) + 3H2O (g)
 Up to about 20% ethanol has been used as a fuel-additive in vehicles
 As a renewable resource:
o Ethanol can be a renewable resource because it can be derived from non-fossil fuel sources, such as the
fermentation of glucose from plants such as sugar cane
o Also, the products from ethanol's combustion - carbon dioxide and water - are reactants in photosynthesis
reactions for plants
o This forms a continuous cycle and thus ethanol is a renewable resource

describe conditions under which fermentation of sugars is promoted.

 The conditions that promote the fermentation of sugar are:
o a suitable micro-organism such as yeast
o Time- 3–5 To allow the ethanol to be produced and fermented
o pH: 3.7–4.6- low pH prevents pathogens from growing
o suitable temperature – about 37oC, more rapid bulk fermentation of sugars
o low oxygen concentrations - favors the fermenting yeast
o a small amount of yeast nutrients to allow the yeast to flourish
 Once the ethanol concentration reaches 14-15% by volume, the yeast cannot survive, and the fermentation process stops.

summarise the chemistry of the fermentation process.

 Yeast is added to mashed grain and water.
 The yeast and other microbes break down the large carbohydrates (e.g. starch or sucrose) into simple sugars (glucose or
fructose) which are then fermented.
o sucrose + water glucose + fructose
C12H22O11 (aq) + H2O (l) C6H12O6 (aq) + C6H12O6 (aq)
 In an oxygen-free atmosphere, the yeast use their enzymes to break down the sugars, forming ethanol and CO 2 as products.
o glucose/fructose ethanol + carbon dioxide
Fermentation =>C6H12O6 (aq) 2C2H5OH (aq) + 2CO2 (g)
 When ethanol concentration reaches 15%, the yeast die and fermentation STOPS.
 Distillation is used to obtain higher ethanol concentrations (95-100%).
define the molar heat of combustion of a compound and calculate the value for ethanol from first-hand data.
 The molar heat of combustion is the amount of heat released by the complete combustion (reaction with oxygen gas to
form water and carbon dioxide) of one mole of a substance
 Formula for change in heat:

 For the calculation of the molar heat of combustion of ethanol, the following first hand values, were used (from 2001 HSC,
Q17):

 In this case, the formula for ΔH is applied to the water (the

“system”):
o ΔT = 59 – 19 = 40 K
o m = 250 g = 0.25 kg
o C = 4.18 x 103 J kg -1 K -1 (This value is a constant for
water; given in exams)
 Therefore: ΔH = –0.25 x 4.18 x 103 x 40
= –41800 joules (J)
= –41.8 kJ
 But the change in mass of the burner was 2.3 grams, therefore
only 2.3 grams of ethanol was combusted.
 Moles = mass / molar mass [of ethanol] = 2.3 / 46 = 0.05 mol
 Therefore, –41.8 kJ/0.05 mol = –836 kJ/mol
 Hence, the experimental molar heat of combustion of ethanol is –
836 kJ/mol

assess the potential of ethanol as an alternative fuel and discuss the advantages and disadvantages of its use.
Although there are arguments for and against the potential of ethanol as a fuel, it seems that the benefits it provides as a fuel are
offset by its negative impacts on society.
Advantages Disadvantages
 Ethanol can be produced from renewable resources of  large areas of farm land would have to be used for the
sugar and starch derived from sugar cane, corn, wheat production of crops for fuel instead of food.
and other cereals. It would relieve some strain on our  the energy required to grow and harvest the crops,
rapidly depleting petroleum resources. distil the ethanol, and transport it to its markets is
 cars running on E10 (10% ethanol, 90% petrol) emit huge
less pollutants into the atmosphere, especially CO,  Today’s engines would need modification to use high
than purely petrol based vehicles concentration ethanol
 Ethanol has a lower heat of combustion per gram
/mole. This means more needs to be burned to get
the same amount as petroleum.
identify the IUPAC nomenclature for straight-chained alkanols from C1 to C8.
 The number of carbon atoms in the chain is given by the prefix as follows:
Number of carbon atoms 1 2 3 4 5 6 7 8
Prefix meth eth prop but pent hex hept oct

 The presence of the –OH, substituting for an H on one of the carbons is indicated by the suffix 'ol'
 If there is more than one hydroxyl group:
No. of OH’s 1 2 3 4
Suffix -ol -diol -triol -tetraol

 The middle syllable 'an' indicates that there are no double or triple bonds:
Recall:
o ‘ane’ = single bonds
o ‘ene’ = at least 1 double bond
o ‘yne’ = at least 1 triple bond
 A number is used to indicate which carbon has the –OH attached to it (count from closest end of chain)
 Numbers and letters in IUPAC nomenclature are linked with a hyphen
 General formula for alkanols: CnH2n+1OH
 Methanol = CH5OH

Process information from secondary sources to summarise the processes involved in the industrial production of ethanol from
sugar cane.
The general process:
 Sugar cane (glucose) fermentation  an ethanol and water
 Distillation of the ethanol and water mixture separates ethanol from the water

The complete process:

 The sugar-cane crop is harvested; the whole plant is then crushed and grinded to create a cellulose/sugar pulp.
 Hydrolysis of the cellulose into glucose molecules.
 The mixture is filtered to separate the glucose solution from the solid residues
 The solution is then placed in an oxygen-free tank, warmed to 37°C, and suitable yeast cultures are added.
 After 15% concentration is reached, the solution is distilled to produce high concentration industrial grade ethanol.

solve problems, plan and perform a first-hand investigation to carry out the fermentation of glucose and monitor mass changes.
Glucose can be fermented using the following procedure:

o Place the following in a flask:

o About 50 grams of glucose.
o About 150 millilitres of water.
o A few crystals of citric acid.
o About 5 grams of yeast.
o Measure and record the mass of the flask.
o Attach an airlock apparatus containing limewater to the top of the flask.
o Stand the flask in a warm place, with a temperature of approximately 37°C, for three days.
o Over the three days, carbon dioxide should be produced, which will form a white precipitate in the limewater (calcium
carbonate) as it bubbles through.
o Measure and record the mass of the flask at various times throughout the three days.
 o Due to the production and release of carbon dioxide, a mass loss should be observed.

present information from secondary sources by writing a balanced equation for the fermentation of glucose to ethanol.
 The equation for the fermentation of glucose is:

Identify data sources, choose resources and perform a first-hand investigation to determine and compare heats of combustion of
at least three liquid alkanols per gram and per mole.

o Measure and record the mass of a burner containing ethanol.

o Measure 100 mL of water into a beaker and measure the temperature of the water.
o Place the beaker of water directly above the burner and light it.
o Allow the burner to heat the water for one minute, then extinguish it.
o Immediately measure and record the mass of the burner and the temperature of the water.
o Calculate the change in mass and the change in temperature.

Substitute the experimental results into the formula below to determine the enthalpy change