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A2 Chemistry Summary

Test for anions after nucleophilic substitution of a Haloalkane Anion 1. Chloride in solution (Cl-1) 2. Bromide in solution (Br-1) 3. Iodide in solution (Br-1) Further test for halides (confirmation test) Test Acidify with dil. nitric acid and add silver nitrate 1. Add dilute ammonia 2. Add conc ammonia 3. In conc ammonia Test Result 1. White ppt produced (AgCl) 2. Cream ppt produced(AgBr) 3. Yellow ppt produced (AgI) 1. Silver Chloride ppt will dissolve 2. Silver bromide will dissolve 3. Silver iodide is insoluble in both

Anion Carbonate (CO32-) Distinguish between Hydrogen Carbonate (HCO31-) and Carbonate (CO32-)

Test Add dil. Acid 1. Add U.I. 2. Additionally you can add Phenolphthalein 3. Add Calcium Chloride to CO32or HCO34. MgSO4, then heat

Test Result Effervescence, CO2 produced

1. if the solution is blue you


have carbonate (pH 12), if it is dark green you have hydrogen carbonate (pH 9). If the solution is dark pink you have a carbonate and light pink with hydrogen carbonate White ppt with carbonate Cloudy solution White ppt produced (AgCl) Cream ppt produced(AgBr) Yellow ppt produced (AgI)

2.

3. 4.
4. Chloride in solution (Cl-1) 5. Bromide in solution (Br-1) 6. Iodide in solution (Br1 ) Further test for halogens (confirmation test) Acidify with dil. nitric acid and add silver nitrate 4. 5. 6. 1. Add dilute ammonia 2. Add conc ammonia 3. In conc ammonia

Iodide in solution (I-1) Nitrate in solution (NO3-1) Sulphate in solution (SO42-)

1. Silver Chloride ppt will dissolve 2. Silver bromide will dissolve 3. Silver iodide is insoluble in both Acidify with dil. nitric acid Bright yellow ppt produced, PbI2 and add lead (II) nitrate Add sodium hydroxide and Ammonia gas produced aluminium foil and heat gently Acidify with dil nitric acid White precipitate, BaSO4 and add barium nitrate

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Organic compound tests

Organic molecule Alkenes

Test Shake with bromine water, goes from orange/brown to colourless Alkanes do not react and the solution remains orange/brown Also alkaline KMnO4 can be added, it goes from purple to colourless and a diol is made (also K2Cr2O7 in acid). Also when burned alkenes make a sooty flame Acidified K2Cr2O7 is added Primary go from orange to green and aldehyde is made if apparatus is set to distil immediately after production. If set to reflux then an organic acids is made Secondary go from orange to green and ketones are made (set to reflux) Tertiary do not oxidise and it stays orange Additionally you can add SOCl2 or PCl5 and misty fumes of HCl are produced Reduces Benedicts solution brick red/orange ppt formed of Cu2O. Organic acid formed from oxidation. Reduces ammonical silver nitrate silver mirror formed (Ag metal formed). Organic acid formed from oxidation. Reduces Fehlings solutionbrick red/orange ppt formed of Cu2O. Organic acid formed from oxidation. Acidified K2Cr2O7 is added the colour changes from orange to green and an the organic acids is made All the above tests are negative for ketones as it does not further oxidise Add iodine and sodium hydroxide. Straw coloured ppt formed of CI3H and an acid with one less carbon. Iodoform reaction (also distinctive smell) Add 2,4 Dinitro Phenyl hydrazine, if a carbonyl is present a orange ppt is formed. This can be test for a sharp mpt compared to standard figures to ID compound Add a carbonate, effervescence of CO2 is observed limewater milky Add sodium hydroxide and heat, then acidified silver nitrate (see anion test for halogens results)

Alcohols

Aldehyde

Ketone RCO-CH3 or RCHOHCH3 Carbonyls (Aldehyde and Ketone) Organic acids Haloalkanes

Physical analysis of organic compounds Test IR data Result Measures bond lengths C=O 1680-1750 cm-1(Strong sharp and broad, not as broad as OH) C=C 16201680 cm-1 C-O 1000-1300 cm-1 C-H 2850-3300 cm-1 O-H 3230-3550 (broad) 2500-3000 (COOH broad) Tables provided in the exam Measures compound masses recognised by M/z and fragmentation patterns. M/z should be the largest peak and the one to the furthest right. Fragments of +CH3 = 17, +CH2CH3 = 29, + CH2 CH2CH3 = 43 Measures the coupling of hydrogen in organic compounds Test for chromophores, need series of double bonds and lone pairs of electrons.

Mass spec data NMR data UV/Vis data

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Carbonyls RC=O + LiAlH4 = RCH2OH (dry ether) Reduction RC=O + KCN = RCHOHCN (Nuc addition) RC=O + RMgX = RCHOHR (in dry solvent after acid workup, Grignard reagent makes 1o/2o/3o alcohols) Reactions of alcohols CH3CH2OH + H2SO4 = C3H6 + H2O (170oC) CH3CH2OH + K2Cr2O7 = Aldehydes/ketone/acid Carboxylic acids and Esters Hydrolysis RCOOR + H2O = RCOOH + ROH (acid catalyst) RCOOR NaOH = RCOONa + ROH RCOOH + LiAlH4 = RCH2OH RCOOR + LiAlH4 = 2RCH2OH RCH2OH + RCOOH = RCOOR + H2O Halogenation of alcohols PCl5 + C2H5OH = POCl3 + C2H5Cl + HCl NaBr in Conc H2SO4 makes HBr which brominates the -OH Phosphorus and Iodine makes PI3 which iodinates the OH Haloalkanes CH3CH2X + NaOH = Nucelphilic substitution of halogen when in aqueous medium. CH3CH2X + NaOH = Elimination when in ethanolic medium with high conc NaOH and high temp

Stability of carbo-cations 1o 2o 3o This means that for an unsymmetrical alkene that reacts with HBr two possible products will be formed. 2o or 3o will be preferred. Primary carbo-cations are not stable (Markovnicovs rule)

Acid Chloride RCOCl + NH3 = RCONH2 + HCl RCOCl + RNH2 = RCONH2R + HCl RCOCl + ROH = RCOOR + HCl RCOCl + H2O = RCOOH + HCl Nitriles RCN + HCl = RCOOH + NH4Cl Hydrolysis RCN + NaOH = RCOONa + NH3 RCN + LiAlH4= RCH2NH2 Reduction KCN + CH3CH2Br = CH3CH2CN + KBr (in ethanolic medium) Amides and amines RCONH2 + P4O10 = RCN + H2O RCH2NH2 + HCl = RCH2NH3Cl (Chloro salt) RCH2NH2 + RCOCl = RCH2NHOCR CH3CONH2 + Br2 + 4KOH = CH3NH2 + K2CO3 + 2KBr + 2H2O (Hofmanns degradation) RCONH2 + LiAlH4 = RCH2NH2 Zwitterions formation Amino acids have amine (-NH2) and organic acid (COOH) groups. This means amino acids can spontaneously gain and lose a proton at the same time at a certain pH H2N-CHCH3COOH = H3N+-CHCH3COO-

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Isomers Need to know that cis/trans are geometrical isomers of alkenes like but-2-ene Chiral centres are carbons that have 4 different groups added. There are two chrial versions of the isomer each is a mirror image of each other and non-super imposable (like the left and right hand). Each is called an enantiomer and a mixture of the two is a racemic mixture. Each enantiomer will polarise light differently L & D, hence why they are called optical isomers. But-1-ene makes Chiral centres when it reacts with HBr. Br- will attaches the more stable 2o carbocation and makes 2-bromo butane (95%) not 1-bromo butane. Side chains addition for pharmaceuticals depending on the site of action To increases the solubility in water addition of Ionic side chains like COO- or NH3+ Polar sides chain like, OH are less effective than full charges To increases the solubility in fat the addition of non-polar side chain can be attached C6H5 phenyl groups are very good CH3 are less effective, the larger the side chain the more fat-soluble it becomes Polymers Ethene C2H4 Propene C3H6 Chloro ethane C2H3Cl Tetrafluoro ethane C2F4 Polyester (Terylene) Polyamides (Nylon) Formula -[ C2H4]-n -[ C2H3CH3 ]-n -[ C2H3Cl ]-n -[ C2F4]-n See structures below See structures below Method of manufacture Addition (free radicals) Addition (free radicals) Addition (free radicals) Addition (free radicals) Condensation Condensation Uses Electrical insulation/plastic bags Ropes and carpets Drain pipes and window frames Non-stick covering for frying pans clothing Clothing/plastic bottles/ sails Clothing/ropes/fishing wire

Note that each monomer in both terylene and nylon has two functional groups on either end to allow polymerisation

Qatar International SchoolAnalysis and summary sheet. Devised by Dr Warrilow/Mr Parry

Qatar International SchoolAnalysis and summary sheet. Devised by Dr Warrilow/Mr Parry

Benzene reactions Mechanisms needed C6H6 + Br2 = no reaction (Br2 is a weak Cl2 + Alkanes = Chloroalkanes + HCl electrophile) (UV light) This is a free radical substitution reaction. C6H6 + H2 = C6H12 (< energy than expected, Homolytic fission Cl2 = 2Cl (free radical Ni cat + heat) production). This is initiation, followed by C6H6 + HNO3 (conc) = C6H5NO2 + H2O propagation using single headed arrow for (conc H2SO4 cat) + movement of 1 electron. Termination is where H2SO4 + HNO3 = HSO4 + H2NO3 + + 2 radical react with each other. This is the same H2NO3 = H2O + NO2 (strong electrophile can mechanism for polymerisation. substitute into the stable benzene ring). Br2 + Alkene = Dibromoalkane. This is Benzene only does electrophilic substitution due electrophilic addition reaction. There is a to the ring stability. Addition reactions mean the partial charge on the Br2 which leads to it loss of the delocalised system and stability. being attracted to the double bond. Br adds C6H6 + CH3Br = C6H5CH3 + HBr (with and the other Br takes both electrons Friedel Crafts carrier AlBr3) making it Br-. A carbocation* is produced. 3Cl2 + C6H6 = C6H6Cl6 (only in the presence Br- then adds to this. *(When using HBr of UV light, this is a free radical reaction) this influences the product made see Reactions of other benzene derivatives stability of carboations). C6H5CH3 + KMnO4 = C6H5COO- (in alkaline Haloalkane + NaOH = Alcohol + NaX. conditions is oxidation of side chain) This is a nucleophilic substitution C6H5NO2 + HCl = C6H5NH2 (with a tin reaction. There is a permanent charge on catalyst) the C-X bond due to the high difference in C6H5CONH2 + P4O10 = C6H5CN (phosphorus electronegativity. This attracts the OH (V) oxide is a dehydration agent) and displaces the halogen. SN2 (Same for C6H5COCH3 + NaBH4/LiAlH4 = other nuc -CN/NH3) C6H5CHCH3OH Tertiary Haloalkane + NaOH = Alcohol These 2 reagents add H- nucleophile which + NaX. This is a nucleophilic substitution attacks carbonyls to make alcohols reaction but the -OH does not displace the C6H5NH2 + HNO2 = C6H5N2+Cl- (diazonium halogen, the C-X bond breaks and forms a ion formed) stable carbocation which then attracts the This is made in situ as it is very unstable. NaNO2 OH. This is an SN1 mechanism + HCl = HNO2 + NaCl Electrophilic substitution of the benzene C6H5N2+Cl- + C6H5OH = C6H5N=NC6H4OH + HCl ring with NO2+ electrophile (this is an azo dye formed as an orange ppt) Nucleophilic addition of HCN to a carbonyl Phenol reactions C6H5OH + 3Br2 = C6H2OHBr3 + 3HBr This is a substitution reaction and the phenol retains the stability of the ring structure. The -OH group activates the molecule and makes it more reactive as benzene will not react with Br2 C6H5OH + NaOH = C6H5O- Na+ + H2O Phenol is slightly acidic and reacts with alkalis, but will not react with HCO3- so can be distinguished from -COOH C6H5OH + CH3COCl = C6H5OCOCH3 + HCl (acts as an alcohol as it reacts with acid chlorides to form phenyl ethanoate) Test for phenol FeCl3 goes purple The proper displayed structural formula for two plastics

Polythene

Solubility Glucose dissolves in water as it has similar bonding due to presence of OH groups I2 dissolves in organic solvents in preference to Qatar International SchoolAnalysis and summary sheet. water as its predominate intermolecular forces is

Polytetrafluoroethene Mass spec and IR


Mass spec is the fragments that are produced when an organic compound is analysed. For butane C4H10 the largest peak will be the actual mass which is 58, this is called the Molecular ion or M+. The fragments Devised by Dr Warrilow/Mr Parry are stable cations and radicals that break off from this. E.g. =15 peak = CH3+

Cation Cr3+

Proton Acquisition Addition of NaOH dropwise From violet solution to Violet ppt or Cr(H2O)3(OH)3
Can be green solution if different ligands are attached From very pale pink to Off white ppt

Ligand Replacement in excess Dissolves slightly to give green solution [Cr(OH)6]3No further reaction No further reaction No further reaction No further reaction No further reaction Dissolves to form colourless solution [Zn(OH)4(H2O)2]2Ligand Replacement in excess Dissolves to form yellow/green solution [Cr(NH3)6]3+ No further reaction No further reaction No further reaction Dissolves to form a lavender solution [Ni (NH3)6]2+ Dissolves to form a dark blue solution [Cu (NH3)4 (OH2 )]2+

Mn2+ Iron (II) (Fe2+) Iron (III) (Fe3+) Ni2+ Cu2+ Zinc (Zn2+)

Mn(H2O)4(OH)2 Dark Green ppt Fe (OH)2 Red/orange ppt Fe (OH)3 Light Green ppt Ni (OH)2 Blue ppt Cu (OH)2 White ppt Zn(OH)2

Cation Cr3+

Proton Acquisition Addition of NH3 dropwise From violet solution to Violet ppt or Cr(H2O)3(OH)3
Can be green solution if different ligands are attached From very pale pink to Off white ppt

Mn2+ Iron (II) (Fe2+) Iron (III) (Fe3+) Ni2+ Cu2+

Mn(H2O)4(OH)2 Dark Green ppt Fe (OH)2 Red/orange ppt Fe (OH)3 Light Green ppt Ni (OH)2 Blue ppt Cu (OH)2

Qatar International SchoolAnalysis and summary sheet. Devised by Dr Warrilow/Mr Parry

Vanadium oxidation states VO2+ 5+ VO2+ 4+ V3+ 3+ V2+ 2+

Colour Yellow Blue Green Lavender

Qatar International SchoolAnalysis and summary sheet. Devised by Dr Warrilow/Mr Parry