Organic Chemistry

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Organic Chemistry by Mind Map: Organic Chemistry

1. Alkanes

1.1. Combustion

1.1.1. Complete

1.1.1.1. CO2+H2O

1.1.2. Incomplete

1.1.2.1. C/CO+H2O

1.2. Free Radical Substitution

1.2.1. UV light/Sunlight

1.2.1.1. Halogenoalkanes

1.2.1.2. CH4+Cl2 → CH3Cl + HCl

1.3. Cracking

1.3.1. Alkene + Alkane

2. Alkenes

2.1. Addition of hydrogen, H2

2.1.1. Nickel,140°C

2.1.1.1. Alkane

2.1.1.2. C2H4 + H2 → C2H6

2.2. Addition of steam, H2O

2.2.1. Concentrated H3PO4,330°C,6MPa

2.2.1.1. Alcohol

2.2.1.2. C2H4 + H2O → C2H5OH

2.3. Addition of hydrogen halides, HX (aq)

2.3.1. HF,HCl,HBr,HI,room temperature

2.3.1.1. Halogenoalkanes

2.3.1.2. C2H4 + HBr → C2H4Br

2.4. Addition of halogens, X2 (aq)

2.4.1. Decolourise

2.5. Mechanism of electrophilic addition

2.6. Oxidation of alkenes

2.6.1. Acidified potassium manganate (VII)

2.6.1.1. Cold dilute KMnO4

2.6.1.1.1. Purple solution turns colourless

2.6.1.2. Hot concentrated KMnO4

2.6.1.2.1. Ketones/Aldehydes/Carboxylic Acids/CO2+H2O

2.7. Addition polymerisation

3. Halogenoalkanes

3.1. Nucleophilic substitution reaction

3.1.1. 1. Aqueous alkali, OH-

3.1.1.1. Alcohol

3.1.1.2. C2H5Br + NaOH → C2H5OH + NaBr

3.1.2. 2. Potassium cyanide,KCN in ethanol (ethanolic)

3.1.2.1. Heat under reflux

3.1.2.1.1. Nitriles

3.1.2.1.2. C2H5Br + KCN → C2H5CN + KBr

3.1.3. 3. Ammonia,NH3 in ethanol

3.1.3.1. Dissolved in ethanol under pressure

3.1.3.1.1. Amines

3.1.3.1.2. C2H5Br + NH3 → C2H5NH2 + HBr

3.2. Elimination reaction

3.2.1. NaOH (Ethanolic)

3.2.1.1. Alkene

3.2.1.2. CH3CHBrCH3 + NaOH → CH2CHCH3 + H2O + NaBr

3.3. Hydrolysis

3.3.1. Heat under reflux : React without evaporating the volatile organic compound

3.3.1.1. Alcohol

3.3.1.2. CH3CH2Br + H2O → CH3CH2OH + HBr

3.4. Mechanism of nucleophilic substitution

3.4.1. 1. Primary halogenoalkanes,SN2

3.4.2. 2. Tertiary halogenoalkanes,SN1

4. Alcohols

4.1. Combustion

4.1.1. CO2+H2O

4.1.2. C2H5OH + 3O2 → 2CO2 + 3H2O

4.2. Substitution

4.2.1. Halogenoalkanes

4.2.1.1. 1. HX

4.2.1.1.1. CH3CH2OH + HCl → CH3CH2Cl + 3H2O

4.2.1.2. 2. SOCl2

4.2.1.2.1. C2H5OH + SOCl2 → C2H5Cl + HCl + SO2

4.2.1.3. 3. PCl5/PCl3

4.2.1.3.1. C2H5OH + PCl5 → C2H5Cl + HCl + POCl3

4.2.1.4. 4. PI3

4.2.1.4.1. 3C2H5OH + PI3 → 3C2H5I + H3PO3

4.3. Reaction with Na

4.3.1. Sodium alkoxide

4.3.2. C2H5OH + Na → C2H5O-Na+ +H2

4.4. Dehydration

4.4.1. Alcohol vapour passed through hot Al2O3 powder/porous pot/pumice

4.4.1.1. Alkene

4.4.1.2. C2H5OH → CH2CH2 + H2O

4.5. Oxidation

4.5.1. Potassium dichromate (VI),K2Cr2O7 acidified with H2SO4

4.5.1.1. 1. Primary alcohol

4.5.1.1.1. Aldehyde → Carboxylic acid

4.5.1.1.2. CH3CH2OH + [O] → CH3CHO + H2O

4.5.1.1.3. CH3CHO + [O] → CH3COOH

4.5.1.1.4. Orange → Green

4.5.1.2. 2. Secondary alcohol

4.5.1.2.1. Ketone

4.5.1.2.2. CH3CHOHCH3 + [O] → CH3COCH3 + H2O

4.5.1.2.3. Orange → Green

4.5.1.3. 3. Tertiary alcohol

4.5.1.3.1. Remains orange, no reaction

4.5.2. Solution warmed

4.5.3. Distinguish primary,secondary & tertiary alcohol

4.6. Heated under reflux with strong acid catalyst, conc H2SO4

5. Carboxylic Acids

5.1. Preparation

5.1.1. From nitriles

5.1.1.1. Reflux with dilute HCl

5.1.1.2. Hydrolysis

5.1.1.3. CH3CH2CN + HCl + 2H2O → CH3CH2COOH + NH4Cl

5.2. Reacting as acids

5.2.1. Weak acid

5.2.1.1. Do not dissociate completely

5.2.1.2. CH3COOH ⟺ CH3COO- + H+

5.3. Reduction

5.3.1. Tetrahydridoaluminate,LiAlH4 in dry ether

5.3.1.1. Reacts violently with water

5.3.2. Sodium borohydride,NaBH4

5.3.3. Alcohol

5.3.3.1. CH3COOH + 4[H] → CH3CH2OH + H2O

5.4. Heated under reflux with strong acid catalyst, conc H2SO4

6. Aldehydes

6.1. Preparation

6.1.1. Primary alcohol

6.1.2. Acidified potassium dichromate (VI)

6.1.3. Heated gently

6.1.4. CH3CH2CH2OH + [O] → CH3CH2CHO + H2O

6.1.5. Orange → Green

6.1.6. Aldehyde need to be distilled off as soon as it is formed to prevent further heating which produces carboxylic acid

6.2. Reduction

6.2.1. Primary alchohol

6.2.2. LiAlH4 in dry ether

6.2.3. Aqueous NaBH4

6.2.4. CH3CHO + 2[H] → CH3CH2OH

6.3. Nucleophilic addition with HCN

6.3.1. Nitriles

6.3.2. CH3CH2CHO + HCN → CH3CH2CH(OH)CN

6.3.3. Mechanism

7. Ketones

7.1. Preparation

7.1.1. Secondary alcohol

7.1.2. Acidified potassium dichromate (VI)

7.1.3. Heated

7.1.4. CH3CH(OH)CH3 + [O] → CH3COCH3 + H2O

7.1.5. Do not further oxidise, do not distil out

7.2. Reduction

7.2.1. Secondary alcohol

7.2.2. LiAlH4 in dry ether

7.2.3. Aqueous NaBH4

7.2.4. CH3COCH3 + 2[H] → CH3CH(OH)CH3

7.3. Nucleophilic addition with HCN

7.3.1. Nitriles

7.3.2. CH3COCH3 + HCN → CH3C(OH)CH3CN

7.3.3. Mechanism

8. Esters

8.1. Esterification

8.1.1. Reversible

8.1.2. Sweet & fruity smell

8.1.3. Flavourings,perfumes,solvents

8.1.4. C2H5OH + CH3COOH → CH3COOC2H5 + H2O

8.1.5. First part : Alcohol Second part : Carboxylic acid

8.2. Hydrolysis

8.2.1. Reflux with acid/base

8.2.1.1. 1. Acid

8.2.1.1.1. Alcohol + Carboxylic acid

8.2.1.1.2. Reversible

8.2.1.1.3. CH3COOC2H5 + H2O ⟺ CH3COOH + CH3CH2OH

8.2.1.2. 2. Alkali

8.2.1.2.1. Soluble base, NaOH (aq)

8.2.1.2.2. Not reversible

8.2.1.2.3. Alcohol + Sodium salt of COOH

8.2.1.2.4. CH3COOCH2CH3 + NaOH → CH3COO-Na+ + CH3CH2OH

9. Nitriles

9.1. Hydrolysis

9.1.1. Carboxylic acid

9.1.2. Reflux with dilute HCl

9.1.3. -CN + H+ + H2O → -COOH + NH4+

9.2. Reduction

9.2.1. Amine

9.2.2. Sodium and ethanol

9.2.3. -CN + 4[H] → -CH2NH2

10. Test for Aldehydes & Ketones

10.1. 2,4-dinitrophenylhydrazine (2,4-DNPH)

10.1.1. Orange precipitate

10.2. Tollens' Reagent

10.2.1. Aqueous AgNO3 in excess NH4 solution (Ammoniacal Silver Nitrate solution)

10.2.2. Mild oxidising agent

10.2.3. Ag+ oxidise an aldehyde to form carboxylate ion

10.2.4. Aldehydes : Silver mirror

10.2.5. Ketones : No reaction

10.3. Fehlings'/Benedict's solution

10.3.1. Copper (II) ions as oxidising agent

10.3.2. Aldehyde oxidised to carboxylate ion & Cu2+ → Cu+

10.3.3. Aldehydes : Clear blue → brick red precipitate

10.3.4. Ketones : No reaction