Organic Chemistry

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Organic Chemistry by Mind Map: Organic Chemistry

1. Carboxylic Acid

1.1. Physical Properties

1.1.1. -COOH

1.1.1.1. ____oic acid

1.1.2. C=OO, carboxylate acid

1.1.3. COOH as 1st carbon

1.1.4. miscible in water

1.1.5. relative molecular mass increase, the solubility decreases

1.1.6. non polar carbon chain increase, solubility increase

1.1.7. the acidity depends on the number of electron withdrawing or donating groups (in notes)

1.1.8. the acidity depends on the number of electron withdrawing or donating groups (in notes)

1.2. Preparations

1.2.1. Oxidation of 1' alcohol or aldehyde

1.2.1.1. ethanol/aldehyde + NaCr2O7 (with diluted sulphuric acid) -> carbox acid + H2O (reflux)

1.2.2. Hydrolysis of Nitriles

1.2.2.1. ____CN + H20 +conc. HCl -> carbox axid + NH4Cl (reflux)

1.2.3. Hydrolysis of Esters

1.2.3.1. using aqueous acid or base solutions

1.2.3.2. _____oate + (solutions) -> carboxylic acid + alcohol + base/acid

1.3. Reactions

1.3.1. Reactions of OH group

1.3.1.1. Reaction with alkalis (neutralisation of base)

1.3.1.1.1. carbox acid + base -> salt (ester/ethanoate) + water

1.3.1.2. Reaction with metals

1.3.1.2.1. carbox acid + metal -> metal ester + H2

1.3.1.3. Reactions with alcohols (esterification)

1.3.1.3.1. carbox acid + alcohol (with a few drops of conc. H2SO4) -> ethyl ester

1.3.1.4. Reactions with phosphorus chloride

1.3.1.4.1. carboxylic acid +PCl5 -> acyl chloride/acid chloride + POCl3 + HCl (steamy white fumes produced is -OH)

1.3.2. Reactions of Alkyl group, CH

1.3.2.1. Halogenation

1.3.2.1.1. Cl bubbled through boiling ethanoic acid + iodine/red phosphorus + sunlight -> chloroethanoic acid + HCl

1.3.2.1.2. carboxylic acid + Cl2 -> Cl___COOH + HCl

1.3.3. Reactions of Carbonyl group, CO

1.3.3.1. carboxylic acid + LiAlH4 -> 1' alcohol (at 25dc in dry ether)

1.4. Esters

1.4.1. ______oate, COOC

1.4.2. carboxylic acid + alcohol -> esters

1.4.3. Physical Properties

1.4.3.1. soluble in organic solvent, not in water

1.4.3.2. fruity smell

1.4.3.3. long chain ester (oil/fats) bad smell

1.4.4. Reactions

1.4.4.1. reacts with water, OH, NH4 and reducing agents

1.4.4.2. Hydrolysis of esters

1.4.4.2.1. Acid solution

1.4.4.2.2. Base solution

1.5. Acid Chloride

1.5.1. Physical Properties

1.5.1.1. CHCOCL, pungent smell, colourless

1.5.1.2. carboxylic acid + PCl5 -> acyl chlorides + POCl3 + HCl

1.5.2. Reactions

1.5.2.1. Hydrolysis of acid chloride

1.5.2.1.1. AC + H20 (cold) -> carboxylic acid

1.5.2.2. Formation of Esters when treated with alcohol

1.5.2.2.1. AC + alcohol -> alkylester + HCl

1.5.2.2.2. addition and elimination

1.5.2.3. Formation of Amides when treated with ammonia or amine

1.5.2.3.1. AC + NH4/1' Amine/2' Amine -> amides + HCl (at 25dc)

1.5.2.4. Reduction of Acid Chloride to form 1' alcohols

1.5.2.4.1. AC (LiAlH4 in dry ether) -> alcohol

1.6. New node

1.7. Acyl Anhydrides

1.7.1. Physical Properties

1.7.1.1. ___oic anhydride

1.7.2. Reactions

1.7.2.1. similar to acid chloride but reacts slower

1.7.2.2. AC + alcohol -> acyl ester + carboxylic acid

2. Alcohol

2.1. Physical Properties

2.1.1. C-OH

2.1.2. 1st carbon closest to OH

2.1.3. 1'<2'<3'

2.1.3.1. no. of carbon atoms increase, solubility decrease

2.1.3.2. boiling point: branched carbon chains lower than unbranched carbon chain

2.1.3.3. solvent, polar end soluble in polar, non polar end in non polar

2.2. Preparations

2.2.1. Indirect hydration of alkenes

2.2.1.1. ethene + conc. H2SO4 -> CH3CH2HSO4 (ethyl hydrogen sulphate) (at room temperature or 80degree)

2.2.2. hydrolysis of alkyl halides

2.2.2.1. AH + aqueous NaOH -> AOH + NaH

2.2.2.2. then diluted and distilled

2.2.2.2.1. CH3CH2HSO4 + H20 -> alcohol + H2SO4

2.2.3. Reaction with Grenard Reagents in dry diethyl ether

2.2.3.1. CH3CH2Br + Mg -> CH3CH2MgBr (ethylmagnesiumbromide)(Grenard's reagent)

2.2.3.2. GR + methanal -> alkoxide ion

2.2.3.3. add diluted acid/water

2.2.3.3.1. methanal -> 1' alcohol

2.2.3.3.2. other aldehydes -> 2' alcohol

2.2.3.3.3. ketones -> 3' alcohol

2.3. Chemical Reactions

2.3.1. Combustion

2.3.1.1. produces CO2 + H20

2.3.2. Fission of the OH bond

2.3.2.1. Alkoxide

2.3.2.1.1. Na + alcohol -> alkoxide

2.3.2.2. Ester

2.3.2.2.1. alcohol + carboxylic acid (with drops of H2SO4) -> ester (-oate)

2.3.2.3. Oxidation

2.3.2.3.1. Alcohol + KCr/KMnO4

2.3.3. Fission of the CO bond

2.3.3.1. Dehydration of alcohol

2.3.3.1.1. alcohol vapour + Al2O3 -> alkene + H20 (at 35degree)

2.3.3.1.2. alcohol + conc. H2SO4/phosphoric acid -> alkene + H2O (at 170-180degree)

2.3.3.1.3. dehydation of 2' alcohol and 3' alcohol -> random formation and cis trans bonds

2.3.3.2. Reaction with hydrogen halide

2.3.3.2.1. alcohol + hydrogenhalide -> Alkyl Halide

2.3.3.3. Reaction with Phosphorus Halide

2.3.3.3.1. alcohol + PCl5 -> chloroalkene + POCl3 + HCl

2.4. Test

2.4.1. Lucas Test HCl+ZnCl2

2.4.1.1. 3' alcohol - turns cloudy immediately

2.4.1.2. 2' alcohol - cloudy after a few min

2.4.1.3. 1' alcohol - no reaction

3. Alkyl Halides

3.1. Rate of Reaction

3.1.1. F<Cl<Br<I

3.1.2. 3'<2'<1'

3.1.3. all single bonds, 1st C closest to halogen

3.2. Preparations

3.2.1. H2SO4 + NaBr -> Hbr + NaH2SO4

3.2.2. HBr + alcohol -> bromoalkane + H20

3.3. Reactions

3.3.1. Nucleophilic Substitution

3.3.1.1. Hydrolysis

3.3.1.2. AH + aqueous NaOH -> alcohol + sodiumhalide (reflux)

3.3.1.3. Formation of Amines

3.3.1.4. ammonia in alcohol + AH -> primary amine

3.3.1.5. add NH4

3.3.1.5.1. -> ethylammonium ion + halogen

3.3.1.5.2. -> ethylamine + NH4halogen

3.3.1.6. add AH

3.3.1.6.1. -> diethylamine

3.3.1.6.2. -> triethylamine

3.3.1.6.3. -> tetraethylamine

3.3.1.7. Formation of Nitriles

3.3.1.8. AH + KCN -> AH-CN + KH

3.3.1.9. hydrolysis of nitriles -> carboxylic acid

3.3.2. Elimination Reaction

3.3.2.1. AH + NaOH in ethanol -> alkene + halide + H20 (reflux)

3.4. Tests

3.4.1. halogen

3.4.1.1. AH + NaOH in ethanol and water -> alcohol + sodiumhalide

3.4.1.2. add dilute AgNO3

3.4.1.2.1. AgNO3 + halogen -> Aghalide + HNO3

3.4.1.3. results

3.4.1.3.1. AgCl - white precipitate, dissolves in dilute ammonia

3.4.1.3.2. AgBr - creamy precipitate, dissolves in conc. ammonia

3.4.1.3.3. AgI - yellow precipitate, insoluble

4. Aldehydes and Ketones

4.1. Aldehydes, C=O

4.1.1. methanal, ethanal, propanal etc

4.1.2. CHO as first carbon

4.1.3. Preparation

4.1.3.1. Oxidation of 1' alcohol

4.1.3.1.1. 1' alcohol + KCr2O7 -> ___al

4.1.3.2. Dehydrogenation of 1' alcohol

4.1.3.2.1. 1' alcohol vapour (pass through Cu) -> _____al + H2 (at 300degree,c)

4.1.3.3. Ozonolysis of alkenes

4.1.3.3.1. alkene + O3 + Zn/H+ -> aldehyde + aldehyde

4.1.4. Reaction

4.1.4.1. Reduction

4.1.4.1.1. becomes 1' or 2' alcohol using NaBH4 or LiAlH4 (+2H)

4.2. Ketones, C=O-C

4.2.1. -one

4.2.2. 1st carbon closest to ketone group

4.2.3. Preparation

4.2.3.1. Oxidation of 2' alcohol

4.2.3.1.1. 2' alcohol + KCr + diluted sulphuric acid -> ketone + H20

4.2.3.2. Dehydrogenation of 2' alcohol

4.2.3.2.1. 2' alcohol (pass through Cu) -> ketone + H2 (at 300dc)

4.2.3.3. Friedel-Craft's acylation of benzene

4.2.3.3.1. C6H5 + CH3COCl (ethanoyl chloride) (with AlCl3 in H20) -> C6H5COCH3 + HCl

4.2.3.3.2. C6H5 + CH3COOCOCH3 (ethanoic anhydride) (with AlCl3 in H20) -> C6H5COCH3 + ethanoic acid

4.2.4. Reactions

4.2.4.1. Nucleophilic Addition

4.2.4.1.1. Formation of Nitriles

4.2.4.1.2. Formation of Amines

4.2.4.1.3. Formation of Carboxylic Acid

4.3. Test

4.3.1. 2,4 dinitrophenylhydrazine (2,4DNPH) or Brady's Reagent

4.3.1.1. aldehyde turns yellow

4.3.1.2. ketone turns orange

4.3.2. Tollen's Reagent

4.3.2.1. aldehydes only

4.3.2.1.1. aldehyde + 2ag+ ->2Ag (silver coverings formed on the walls of test tube)

4.3.3. Fehling's Solution, CuO

4.3.3.1. aldehydes only

4.3.3.1.1. Cu2+ -> Cu20 (blue to brick red)

4.3.4. Iodoform Test

4.3.4.1. ethanal and all ketones

4.3.4.2. to test the presence of C=O

4.3.4.3. ethanal/ketones + iodine + NaOH (warm) -> yellow precipitate