AS Organic Chemistry Reactions

Halogenoalkane to Amine

Halogenoalkane to Amine

• Nucleophilic substitution

• NH3 in ethanol

• Heat under pressure

Acidic Hydrolysis of Nitriles

• Nucleophilic substitution

• Dilute HCl or H2SO4 solution

• Heat

• Product: Carboxylic Acid

Nitrile to Primary Amine

• Reduction

• Hydrogen gas

• Platinum catalyst

Primary Alcohol to Halogenoalkane

• Hydrogen Halide (HCl), SOCl2, PCl3 and heat

• PCl5 (room temperature)

Carboxylic Acid to Primary Alcohol

• Reduction

• LiAlH4

• By-product: H2O

Alkane to Halogenoalkane

• Free radical Substitution

• Cl2

• UV

Alkane to Alkene

• Al2O3

• Heat (under reflux)

Alkene to Polyalkene

• Addition polymerisation

Alkene to Alkane

• Hydrogenation

• Hydrogen

• Nickel/Platinum

• Heat

Alkene to Diols

• Oxidation

• Cold, dilute acidified KMnO4

• Room temperature

• alkene + H2O + [O] → diols

Alkene + Halogen Solution

• Br2 (aq)

• Room temperature

• Electrophilic Addition

• Decolourisation of halogen solution (orange/red brown to colourless)

Alkene to Primary Alcohol

• Electrophilic additon

• Steam OR H2O (g)

• concentrated H3PO4 as catalyst

• Heat

  • 330 degrees celsius

  • 6 MPa

Alkene to Halogenoalkane

• EA

• Hydrogen Halide gas (HBr, HCl, etc)

• Room temperature

Primary Alcohol to Halogenoalkane

Halogenoalkane

• H-X

• Heat under reflux

• By-product: H2O

Primary Alcohol With Na(s)

• Na (s)

• Sodium alkoxide + Hydrogen

• CH3CH2OH + Na → CH3CH2O-Na+ (s) + H2

Primary Alcohol to Aldehyde

• By distillation

  • Reagents:

    • Acidified KMnO4 (purple → colourless)

    • Acidified K2Cr2O7 (orange → green)

Primary Alcohol to Carboxylic Acid

• Acidified KMnO4 or K2Cr2O7

• Reflux

Oxidation of Secondary Alcohols

• Ketone + H2O

• K2Cr2O7/H+ or KMnO4/H+

• CAN’T be oxidized to -COOH

Tollen’s Reagent

• AgNO3 (aq) + NH3 (aq) → [Ag(NH3)2]+

• Aldehyde: Silver mirror (or dark grey solution) -CHO

• Ketone: No silver mirror

2,4-DNPH

• Carbonyl compound (C=O)

• Positive result: Deep orange ppt

• Condensation

• Warm

Fehling’s Solution

• Contains Cu (II) ions

  • Acts as oxidising agent

• Clear blue solution → Red/orange ppt

• Positive result: Aldehyde

• Negative result: Ketone

Triiodomethane Test

• Iodine in NaOH (aq)

• CH3C=O group

• CH(CH3)OH group

• Product: COONa salt + CHI3 (yellow ppt)

Aldehyde/Ketone to Hydroxynitrile

• Nucleophilic Addition

• HCN

• Catalyst: KCN/NaCN + H2SO4

• Heat

Reduction of Aldehyde

• Product: Primary Alcohol

• LiAlH4 or NaBH4

• CH3CHO + 2[H] → CH3CH2OH

Reduction of Ketones

• Product: Secondary alcohol

• NaBH4 or LiAlH4

• CH3COCH3 + 2[H] → CH3CH(OH)CH3

Hydrolysis of Hydroxynitrile

• Product: hydroxy acid

• Hydrolysis

• Dilute HCl or H2SO4

• Heat

• 2-hydroxypropanenitrile → 2-hydroxypropanoic acid

Hydroxynitrile to Hydroxyamine

• Hydrogen

• Platinum catalyst

• Heat

• Reduction

• 2-hydroxypropanenitrile → 2-hydroxypropaneamine

Oxidation of Aldehyde

• -COOH is formed

• Heat under reflux

• Alkaline & Acidic conditions

• Acidic:

  • RCOOH

• Alkaline: RCOO-

Reduction of Carboxylic Acids

• Product: Primary Alcohol

• Reagent: LiAlH4

• Room temperature

• By-product: H2O

Carboxylic Acids to Esters

• Condensation reaction

• Reagents: Alcohol + Conc. H2SO4

• Heat

Carboxylic Acid & Na (s)

CH3COOH + Na → CH3COO-Na+ & H2

Hydrolysis of Ester + Alkali

• NaOH (aq)

• Heat

• Ethyl ethanoate + NaOH → sodium ethanoate + ethanol

Hydrolysis of Esters + Acid

• Dilute acid

• Ethyl ethanoate + H2O → ← Ethanoic acid + ethanol

Carboxylic Acid & Base

• CH3COOH + KOH → CH3COO-K+
  + H2O

Carboxylic Acid & Carbonates

• CaCO3

• Room temperature

• (CH3COO)2Ca + CO2 + H2O

Primary Alchol to Bromoalkane

Bromoalkane

• KBr with conc. H2SO4/H3PO4

  • KBr + H2SO4 → KHSO4 + HBr

  • HBr + CH3CH2OH → CH3CH2Br + H2O

• Heat

• By-product: H2O

Primary Alcohol to Chloroalkane (PCl3)

Chloroalkane

• PCl3

• Heat

• By-product: H3PO3 (phosphorous acid)

• Nucleophilic substitution

Primary Alcohol to Chloroalkane (SOCl2)

Chloroalkane

• SOCl2

• Room temperature

• By-products: HCl (g), SO2 (g)

Primary Alcohol to Chloroalkane (PCl5)

Chloroalkane

• PCl5

• Room temperature

• By-products: HCl (g), POCl3

  • Observation: Dense white fume (HCl gas)