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Describe and explain the solubility of a dissolving polymer based on polyethenol in terms of its molecular structure insoluble when

n very many or few internal hydrogen bonds;Soluble when an intermediate number of bonds.

H n C H CH2

H C O H

H C

H C O H

CHOH

ethenol monomer

polyethenol polymer

Structure of Slime

H H H C C O H B H O O
-

H O H C H O C H H

+ H

H + H O

polyethenol H borax

H polyethenol hydrogen bonds

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Dissolving Polymers Dissolving polymers are made to combat the risk of infection in hospitals. Laundry bags can be made from polyethenol, meaning that soiled laundry does not have to be handled, as the bags can be put straight into the washing machine. Ethenol (CH2 = CH OH), the monomer from which polyethanol is made is unstable and does not exist. It can be made from another plastic polyethenyl ethanoate by a process of ester exchange.

The extent of reaction can be controlled by adjusting either the temperature or the reaction time. The plastics solubility depends on the percentage of OH groups present. The plastic is soluble in water as the OH groups form hydrogen bonds with water. Different solubilities give the plastic different uses.

% OH Groups 100 99 99 -97 96 90 Below 90

Solubility in Water Insoluble Soluble in hot water Soluble in warm water Soluble in cold water

Explanation

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Recognise and use the term addition polymerisation and predict the structural formula of the addition polymer formed from given monomers and vice versa.

The double bonds in alkenes can open up and join together to make long chains called polymers. The individual small alkenes are called MONOMERS.

monomer H n H C C C C H H

polymer H C C H H C C H n side links show that both sides are attached to other units Inside the bracket is the repeating unit

This is called ADDITION POLYMERISATION. The polyethene is made of many ethene monomers.

To find a MONOMER used to form an addition polymer, take the repeat unit and add a double bond H C H CH3 H CH3 C H C H C H H CH3 C H C H CH3 C C H H C C H H CH3 C C C C H H

polymer polypropene CI n H C C C C H H CI C C H H C C H

repeat unit

monomer propene

chloroethene

n polychloroethene (PVC polyvinylchloride)

used to make water pipes, insulation on electric wires.

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F n F C C C C

F C C

F C C F n

Tetra fluoroethene

Polytetra fluoroethene (PTFE) Chemically inert and has non-stick properties used as a coating for frying pans

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Use relevant given date to interpret (and make predictions of) infra red spectra for organic compounds containing a limited range of functional group hydroxyl, carbonyl and carboxylic acid groups. To understand infra red (IR) spectroscopy, it is helpful to think of the bond between any two atoms as being like a vibrating spring. Each bond has its own natural frequency of vibration that depends on the types of atoms forming the bond and the type of bond (single, double, triple). When a molecule is exposed to IR radiation, each bond absorbs energy at a particular frequency causing it to vibrate more vigorously. Different bonds absorb different frequencies of IR radiation. Bonds in different places in a molecule absorb different frequencies too so that the O H group in an alcohol and the O H group in a carboxylic acid absorb different frequencies.

This table shows what frequencies different bonds absorb Where its found Most organic molecules Alcohols Carboxylic acids Aldehydes, ketones, carboxylic acids

Functional Group CH OH OH C=O

Frequency Wavenumber (cm-1) 2800 3100 3200 3550 2500 3300 1680 - 1750

IR spectra have the following features: The x axis shows wavenumber, measured in cm-1, the scale usually starts at around 4000 wavenumbers on the left and descends to about 500 wavenumbers The y-axis shows percentage transmittance the baseline is at the top (100% transmittance) and the absorption signals or bands are downward troughs The part of the IR spectrum below 1500 cm-1 is called the fingerprint region. Every compound has a distinctive fingerprint region which can help in its identification. Absorptions in this region are caused by the bonds in the molecules skeleton eg C - C

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An infrared spectrometer produces a graph that shows what frequencies of radiation the molecules are absorbing.

The absorption of about 3000 cm-1 is caused by the C H groups

Fingerprint region. Peaks show where radiation is being absorbed The peaks on IR spectra are upside-down they point downwards

Absorption about 1700 cm-1 shows there is a C = O group

Wavenumber is the measure used for the frequency (it is 1/wavelength in cm)

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Recognise and write formulae for alkenes and use systematic nomenclature to name and interpret the names of alkenes.

ALKENES are a family of hydrocarbons which contain a double bond between carbon atoms C = C The names of the molecules end in ENE They have a general formula CnH2n Number of carbon atoms Name Molecular formula Structural formula H 2 Ethene C2H4 C C H C C H H

H 3 Propene C3H8 H C H

H C C C

H 4 Butene C4H8 H C H

H C H

H C C C C

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Naming Alkenes

1. Choose the longest chain of carbon atoms that contains the double bond. 2. Number the carbon atoms in the chain from the end nearest the double bond. 3. Pick the carbon atom with the lowest number to describe the position of the double bond

H 4 H C H

H 3 C H

H 2 C C H

H 1 C C H but 1 ene

CH3CH2CH2=CH2

H 4 H C H

H 3 C

H 2 C C

H 1 C C H

but 2 - ene H

CH3CH

CHCH3

CH3CH2CH2CH2CH hex 1 ene

CH2

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CH2

CHCH2Br

3 bromo prop 1 - ene

propene CH3CH

CH2

CH3CH

CHCH2CH2CH2CH3 hept 2 -ene

CH3 CH3CH CHCH3 2methyl but 2 - ene

CH2

CHCH2CH

CHCH2CH3

hepta 1,4 - diene

CH3

CH3

CH3 C

CH3

H 2, 4 dimethylpent 2 - ene

cyclopentene

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Recognise members of the following homologous series aldehydes, ketones, carboxylic acids.

Aldehydes and ketones are carbonyl compounds. They have the functional carbonyl group C = O. Their general formula is CnH2nO Aldehydes have a hydrogen and one alkyl group attached to the carbonyl carbon atom

eg

H C CH3

(hydrogen) O O carbonyl carbon R C H

(alkyl group) methyl Ethanal

Ketones have two alkyl groups attached to the carbonyl carbon

eg

CH3

carbonyl carbon

alkyl groups CH3 propanone

R C R O

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Ketones

R C R O

CH3 C CH3 O propanone

CH3CH2 C CH3 O butanone

CH3CH2CH2 C CH3 O Pentan-2-one

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Aldehydes R

H C O

H C H O methanal

H C CH3 O ethanal

H C CH3CH2 O propanal

H C CH3CH2CH2 O butanal

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Carboxylic Acids

O R C OH

O H C OH methanoic acid HCOOH

O CH3 C OH ethanoic acid CH3COOH

O CH3CH2C OH propanoic acid CH3CH2COOH

O CH3CH2CH2 C OH butanoic acid CH3CH2CH2COOH

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Explain and use the terms thermoplastic, thermoset and co-polymer Thermoplastic is a polymer without cross-links (covalent bonds) between the chains. The intermolecular forces between the chains are weak. These intermolecular forces between the chains are weak. These intermolecular forces of attraction can be overcome by warming. The polymer chains can slide over each other and the polymer can be deformed ie change shape. On cooling the weak intermolecular forces between the polymer chains can reform and the thermoplastic holds its new shape e.g. polyethene, Thermoset this type of polymer has extensive cross linking between the different polymer chains. The cross-links (covalent bonds) between the chains are much stronger than intermolecular forces of attraction found in thermoplastics. The crosslinks (covalent bonds) cannot be broken by warming. The polymer chains cannot move relative to each other and the polymer cannot change shape. If heating continues the polymer just chars and burns e.g. Bakelite. A co-polymer is made when two different monomers become incorporated into a polymer chain.

e.g. ethene and propene.

H C H (A)

H + C + H

H C C H (B)

H C C H

H C C H

H C H

H C H

H C C H

H C C CH3

H C H

H C H

H C C H

H C C CH3

ethene A
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propene B A C B C

Explain and use the term elimination reaction Describe and explain the following properties of alcohols - oxidation of alcohols to carbonyl compounds (aldehydes and ketones) and carboxylic acids with acidified potassium dichromate (VI) solution, including the importance of the conditions (reflux or distillation) under which it is done - dehydration of alcohols to form alkenes using heated AI2O3 or refluxing with concentrated H2SO4

Alcohols can be oxidised using potassium dichromate (VI) K2Cr2O7 acidified with H2SO4. The reaction conditions for the oxidation of alcohols are heating the alcohol under reflux with acidified potassium dichromate. Primary alcohols are oxidised to aldehydes and then to carboxylic acids Secondary alcohols are oxidised to ketones only Tertiary alcohols are not oxidised

Oxidation of primary alcohols Primary alcohols are oxidised to aldehydes if the alcohol is in excess

H H C H

H Cr2O72C H O H C H H
+

H C H ethanal (aldehyde) C

ethanol (excess)

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If an excess of oxidising agent is used primary alcohols are oxidised to carboxylic acids. H H C H H Cr2O72C H O H C H H+ H ethanal H C C H
+

O Cr2O72H

H C H C

O O H

ethanol

ethanoic acid (carboxylic acid)

During the reactions the acidified orange dichromate (VI) ions are reduced to green chromium ions

Cr2O72orange

Cr3+ green

Oxidation of primary alcohol by oxidising agent K2Cr2O7 in dilute H2SO4


2 Cr2 O7 (aq) 8H (aq) 3CH 3CH 2 OH (C) Cr3(aq) 7H 2 O(C) 3CH 3CHO(C)

dichromoate (ORANGE)

ETHANOL alcohol

chromium ions (GREEN)

aldehyde ETHANAL

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Oxidation of a primary alcohol, ethanol to an aldehyde, ethanal. If the alcohol is in excess of the acidified potassium dichromate (VI). The mixture is gently heated in the apparatus below, but with the receiver cooled in ice to reduce evaporation of the ethanal.

DISTILLATION APPARATUS

Ethanal (boiling temperature 21oC) vaporises as soon as it is formed and distils off. This stops it from being oxidised further to ethanoic acid. Unreacted ethanol remains in the flask.

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Oxidation of a primary alcohol, ethanol to a carboxylic acid, ethanoic acid. For a complete reaction, the acidified potassium dichromate is in excess. The mixture is heated in the apparatus shown below.

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Reflux means that vapour condenses and drips back into the reaction flask. While the reaction mixture is refluxing, any ethanol or ethanal vapour will condense and drip back into the flask, eventually, it is all oxidised to ethanoic acid. After refluxing, the ethanoic acid (boiling temperature 118oC) can be distilled off by rearranging the apparatus to a distillation apparatus.

Oxidation of secondary alcohols H H C H H C OH H Cr2O72C H H C H H+ H O H C C C H H H

propan 2 - ol

propanone (ketone)

Elimination Reactions Elimination reactions are ones in which a small molecule leaves the parent molecule. In the case of alcohols, this molecule is water so elimination reactions of alcohols are always dehydrations. Alcohols can be dehydrated by refluxing with excess concentrated sulphuric acid or by passing alcohol vapour over heated aluminium oxide AI2O3. An alkene is formed. eg H H H C H H C H H AI2O3 C OH H C H 600K H propene H2O (alkene) H C C C + H2O H H

propan 1 - ol

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Recognise where E/Z isomerism occurs explaining it in terms of lack of free rotation about C = C bonds when there are two different groups on each carbon. Draw and interpret diagrams to represent E/Z isomers for alkenes which have the same groups on both sides of the double bond (E diagonally opposite sides of C = C bond; Z- same side of C = C bond). In such molecules describe E as TRANS and Z as CIS and extend this CIStrans nomenclature to other, more complicated, alkenes.

E/Z isomerism is a form of geometric isomerism OR stereoisomerism. Geometric isomers have the same structural formula but a different arrangement of atoms of groups in space. This is because there is a lack of rotation of atoms or groups attached to the double bonded carbon atoms. When double bonded carbon atoms each have two different atoms or groups attached to them, - an E-isomer and a Z-isomer is produced.

For example the double bonded carbon atoms in each but-2-ene molecule, each have an H and a CH3 group attached.

H C H3C

CH3 C H

H3C C H

CH3 C H

(trans-but-2-ene)

(CIS-but-2-ene)

E-isomer E-but-2-ene When the same groups are ACROSS the double bond it is an E-isomer

Z-isomer Z-but-2-ene When the same groups are BOTH ABOVE or BOTH BELOW the double bond it is an Z-isomer

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E/Z isomerism is sometimes called CIS-TRANS ISOMERISM. Where CIS means the Z isomer, and TRANS means the E-isomer. So E but-2-ene can be called trans-but-2ene, and Z-but-2-ene can be called CIS-but-2-ene. E/Z isomerism is one type of STEREOISOMERISM. In stereoisomerism, the atoms are bonded in the same order but arranged differently in space in each isomer. You can use the CIS-trans system if there are more than two different groups (other than hydrogen atoms) attached around a double bond. F C Br C H CH3

This could be trans-I-bromo-I-fluoropropene because the Br and CH3 are on opposite sides or it could be CIS-I-bromo-I-fluoropropene because the F and CH3 are on the same side. The E/Z system keeps on working. Each of the groups, linked to the double bonded carbons is given a PRIORITY. If the two carbon atoms have their higher priority group on opposite sides, then it is an Eisomer. F C Br C H CH3

E-1 bromo-1-fluoropropene If the two carbon atoms have their higher priority group on the same side, then it is a Z isomer (you do not need to know the rules for deciding the order of these priorities). Br C F C H CH3

Z-1- bromo-1-fluoropropene
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In the E/Z system, Br has a higher priority than F, so the names depend on where the Br atom is in relation to the CH3 group (which has a higher priority than the H atoms).

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Recall the addition reactions of alkenes with the following bromine to give a dibromocompound and the use of this as a test for an alkene hydrogen bromide to give a bromocompound hydrogen in the presence of a catalyst to give an alkane - nickel catalyst with heat and pressure or platinum catalyst at room temperature and pressure water in the presence of a catalyst to give an alcohol (concentrated H2SO4 and then add water or steam/H3PO4 under heat and pressure)

Use bromine water to test for C = C bonds. When you shake an alkene with orange/brown bromine water, the solution quickly decolourises. Bromine is added across the double bond to form a colourless dibromoalkane.

eg

H C H

H C H + Br2 orange brown H

Br C

Br C H

H H 1,2 dibromoethane colourless

ethene

The mechanism is electrophilic addition. carbocation intermediate H C H Br


+

H C H

H H C

H C+ BrxH H

H C Br

H C Br H

Br

x Br
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Hydrogen halides, HCI, HBr and HI, add across a double bond to form a halogen alkane. Example hydrogen bromide and ethane. H C H ethene This happens by electrophilic addition. H C H C H H H H C
+

H C H + HBr H hydrogen bromide

H C H

H C H Br

bromoethane

H C
x -

H H C H

H C H Br

H+
x

Br

BrIn a symmetric alkene like ethene or but-2-ene only one product is formed. If HBr adds to an asymmetric alkene like propene these are 2 possible products. H C H H
+

CH3 C H

BrH H
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CH3 C
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H H H C Br

CH3 C H H

Br

Adding hydrogen to C = C bonds produces alkanes. Ethane will react with hydrogen gas to produce ethane. The reaction needs a nickel catalyst and a temperature of 150oC. H H C H ethene C H H +H2
Ni 150 C

H C H

ethane

Margarine is made by hydrogenating unsaturated vegetable oils.

Adding water across a C = C bond produces alcohols. The reaction is used industrially to make alcohols and is carried out with steam at a suitable temperature 300oC and a pressure of 60-70 atm, using an acid catalyst such as phosphoric acid, H3PO4.

H C H ethene C

H H3PO4 + H2O(g) H(g) 70 atm 300oC CH3CH2OH(g) ethanol

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Recall the difference between primary, secondary and tertiary alcohols from their structures, and identify examples of them. 1. Monohydric Alcohols alcohols with one OH group Primary Alcohol (1o) H H C H C H C O-H

The carbon C bearing the OH group is in turn bonded to one alkyl group in this case CH3CH2-, ethyl group

CH3CH2CH2OH propan-1-ol

Secondary Alcohol (2o) H H C H C H C H The carbon C bearing the OH group is bonded to two alkyl groups e.g. two CH3, methyl groups

O H

CH3CH(OH)CH3 propan-2-ol

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Tertiary Alcohol (3o) H H C H H C H C O H 2 methyl propan-2-ol H H C H H The carbon C bearing the OH group is bonded to 3 alkyl groups e.g. three methyl CH3 groups

Polyhydric Alcohols alcohols with more than one OH group H H C OH H C OH H dihydric alcohol

CH2OHCH2OH Ethane-1,2,-diol

H H C OH

H C OH

H C OH H trihydric alcohol

CH2OHCHOHCH2OH propane-1,2,3-triol
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