OCR AS Chemistry A H032 for first assessment in Complete Tutor Notes. Section: Boomer Publications

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1 R AS hemistry A 032 for first assessment in 2016 omplete Tutor Notes Section: Alcohols aloalkanes 2015 Boomer Publications page 145 page 152

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3 40 Alcohols Page 155 Ethanol can be prepared by the reaction of steam with ethene (hydration) at a high pressure and a high temperature. 2 = 2 (g) + 2 (g) 3 P (l) ethene Alcohols atm ethanol omparison of boiling points of alcohols and alkanes boiling point / alcohols alkanes number of carbons in chain The graph above shows that alcohols have much higher boiling points than their alkane equivalent (with a same number of carbons). With alkanes, induced dipole-dipole interactions need to be overcome to boil them whereas with alcohols, much stronger hydrogen bonds must be overcome an this requires more energy. remember when drawing hydrogen bonds, you must include a dipole across the - bond and then draw a - dotted line going from a lone + + pair on the oxygen of one molecule to the electron hydrogen bond - deficient hydrogen ( +) of another molecule. Label the hydrogen bond.....

4 Page Alcohols Primary, secondary and tertiary alcohols Alcohols are classified as being primary, secondary or tertiary. Primary alcohols have the on the end of a carbon chain, for example: pentan-1-ol 3-methylbutan-1-ol Secondary alcohols have the within the chain so the carbon atom that has the is bonded to 2 other carbon atoms. For example: propan-2-ol With tertiary alcohols, the carbon atom that is bonded to the group is bonded to 3 other carbon atoms.

5 40 xidation of alcohols Alcohols Page 157 Primary alcohols may be oxidised to aldehydes. In doing this it is necessary to set the apparatus up so that the aldehyde is distilled off as soon as it is formed to prevent further oxidation. We show oxidation as follows using the [] to represent a single oxygen being added. We use K 2 r 2 7 as the oxidising agent and 2 S 4 as the catalyst. K 2 r 2 7 / 2 S 4 + [] distil primary alcohol aldehyde (ethanal) + 2 Water out Water out K 2 r 2 7 makes reaction mixture orange to start with Water in Water in apparatus set up to distil off aldehyde product as soon as it is formed as the reaction proceeds the reaction mixture turns green as the K 2 r 2 7 is reduced. 2 S 4 is the catalyst We can oxidise the primary alcohol completely to form a carboxylic acid if we have an excess of potassium dichromate and we do not distil but instead reflux the mixture. Refluxing is the continual evaporation and condensing of a reaction mixture which prevents loss of solvent.

6 Page 158 Alcohols 40 Water out Water in apparatus set up for refluxing + [] K 2 r 2 7 / 2 S 4 reflux aldehyde (ethanal) carboxylic acid (ethanoic acid) Secondary alcohols are oxidised by refluxing to form ketones. They are not oxidised further as the carbon to carbon bond is too strong and is resistant to oxidation. K 2 r 2 7 / + [] 2 S 4 reflux + 2 secondary alcohol propan-2-ol Ketone (propanone) Tertiary alcohols are not oxidised as the carbon-carbon bond is resistant to oxidation.

7 40 Alcohols Page 159 To summarise, primary alcohols are oxidised first to aldehydes and if you want the aldehyde you need to distil immediately. K 2 r 2 7 / 2 S 4 + [] distil primary alcohol aldehyde (ethanol) (ethanal) + 2 If you reflux the reaction mixture with excess potassium dichromate, the aldehyde undergoes oxidation to a carboxylic acid. K 2 r 2 7 / + 2[] 2 S 4 reflux + 2 primary alcohol (ethanol) carboxylic acid (ethanoic acid) Secondary alcohols are oxidised to ketones. K 2 r 2 7 / + [] 2 S 4 reflux + 2 secondary alcohol propan-2-ol Ketone (propanone) Tertiary alcohols are not oxidised as the carbon-carbon bond is resistant to oxidation.

8 Page 160 Alcohols 40 Solubility of alcohols in water Short chain alcohols have high water solubility due to the fact that hydrogen bonds can form between the of the alcohol groups and the water solvent molecules: hydrogen bond Dehydration of alcohols Alcohols can be dehydrated, that is, water removed, when they are refluxed with concentrated sulfuric acid: 2 S reflux When a small molecule like water has been removed from a larger molecule, it is called an elimination reaction. ombustion of alcohols Alcohols undergo complete combustion in a plentiful supply of oxygen. Balancing this type of reaction is similar to balancing combustion of alkane reactions (l) +? 2 (g)? 2 (l) +? 2 (l) In the above case, we have 5 carbons in pentanol so these will form 5 molecules of carbon dioxide. We have 12 hydrogens and these will form 6 molecules of water.

9 Alcohols Page (l) +? 2 (g) 5 2 (l) (l) We now have 16 oxygens on the right hand side. We already have 1 oxygen on the left hand side as part of the pentanol and so we need 7.5 molecules of oxygen to balance: 5 11 (l) + 7½ 2 (g) 5 2 (l) (l) Preparation of haloalkanes from alcohols aloalkanes can be prepared reacting the alcohol with a sodium halide salt and an acid like sulfuric acid. In doing this, the hydrogen halide is formed in situ and the overall reaction can be written like this: X X represents a halogen X + 2

10 Page 162 aloalkanes 41 aloalkanes aloalkanes have the general formula n 2n+1 X where X is a halogen. istorically, haloalkanes have been used as refridgerants, aerosol propellants and dry cleaning agents owing to the fact that they are unreactive, nontoxic and have high volatility. Their use however is in decline since they are believed to be responsible for depletion of the ozone layer. ydrolysis of haloalkanes The polar nature of the carbon to halogen bond makes haloalkanes susceptible to attack from nucleophiles. + X - A nucleophile being something that can donate a pair of electrons to form a bond. The relative reactivities of a series of haloalkanes can be investigated experimentally. If you start with haloalkanes that have the same length of carbon chain but only vary in the halogen they contain. For example, 1-chlorobutane, 1-bromobutane and 1-iodobutane. You then react these with alkali ( - (aq)). The mechanism for such reactions, nucleophilic substitution, is as follows: X + X - Note: Ethanol needs to be added to the aqueous solutions to keep the haloalkanes in solution. The progress of the reaction can be followed by carrying out the reaction in an aqueous solution of silver nitrate in a water bath to provide heat. As halide ions form, they immediately react with the silver ions to produce a precipitate of silver halide. By timing the appearance of a precipitate it is possible to work out the order of reactivity.

11 aloalkanes Page l - + Br - + I - Factors affecting rate of reaction of haloalkanes ut of the 3 haloalkanes being studied, chlorine is the most electronegative and so the carbon to chlorine bond will be the most polar and as a result, it might be expected that the chlorobutane would react the fastest. In fact the reverse is true because bond polarity is only one factor that controls rate of reaction. owever, if we look at bond enthalpies for the carbon to halogen bonds. Bond Enthalpies for arbon to alogen Bonds Bond Enthalpy / kj mol l -Br -I arbon to alogen Bond The graph above shows that the carbon to iodine bond is the weakest and this is why iodobutane undergoes the fastest hydrolysis and so bond enthalpy is the predominant factor in controlling the rate of reaction. The relative rates of reaction for the hydrolysis of the haloalkanes are: iodobutane > bromobutane > chlorobutane fastest precipitates first slowest precipitates last

12 Page 164 aloalkanes 41 The zone Layer The ozone layer is made up of the chemical ozone, 3. When ozone is present in the lower atmosphere it is a pollutant and causes respiratory problems. owever, when ozone is present in the upper atmosphere it absorbs harmful ultraviolet radiation from the sun; radiation that would otherwise cause skin cancer. It was therefore a concern when a hole was discovered in the ozone layer. It is the formation and subsequent breakdown of ozone that absorbs the harmful ultraviolet radiation. The first step is the formation of oxygen atoms from oxygen molecules that requires high energy ultraviolet radiation at less than 240nm wavelength: u 2 (g). v. light <240nm 2(g) These atoms of oxygen can react with oxygen molecules to produce ozone: 2 (g) + (g) 3 (g) The ozone formed can then be broken down into oxygen molecules and atoms of oxygen by absorbing radiation at less than 310nm. The rate at which the ozone is formed is equal to the rate it is broken down and it is this natural balance that absorbs the harmful ultraviolet radiation. 2 (g) + (g) 3 (g) hlorofluorocarbons (Fs) and the zone Layer hlorofluorocarbons, Fs, are harmful to the ozone layer and cause depletion. The first step is the initiation step where the carbon to chlorine bond breaks in the F to produce a chlorine radical. Fl 3 (g) l.(g) +.Fl 2 (g) The breaking down of ozone then follows in two propagation steps:

13 aloalkanes Page l.(g) + 3 (g) l.(g) + 2 (g) propagation step 1 l.(g) + (g) l.(g) + 2 (g) propagation step 2 If we add these two equations we get the following equation. Then if we cancel what is on both sides we end up with the overall breakdown of ozone: l.(g) + 3 (g) + l.(g) + (g) 3 (g) + (g) l.(g) + 2 (g) + l.(g) + 2 (g) 2 2 (g) We notice that in the second propagation step we produce more chlorine radicals which can then react and breakdown more ozone. This is how a single chlorine radical is able to breakdown thousands of ozone molecules. Another radical that breaks down ozone is nitrogen oxide,.n, radical that is formed in jet engines and during lightening. The mechanism is similar to that with chlorine radicals: verall:.n(g) + 3 (g).n 2 (g) + 2 (g) propagation step 1.N 2 (g) + (g).n(g) + 2 (g) propagation step 2 3 (g) + (g) 2 2 (g) The lifetimes of Fs in the upper atmosphere are in the region of 50 to 100 years. Therefore even though the use of Fs has declined due to the Montreal protocol that was an international agreement to reduce F emissions, it may take several lifetimes before the hole in the ozone layer is repaired.

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