A2 chemistry organic reactions

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A2 chemistry organic reactions

  1. 1. A2 Organic Reactions / Reagents & Conditions1. GRIGNARD REAGENTS Preparation: i. HALOALKANE + Mg → GRIGNARD • Reagents and Conditions: 1) Heat under reflux 2) Dry Ether 3) Single Crystal of Iodine catalyst if needed Reactions: i. GRIGNARD + CO2(cold/solid) → (+1C)CARBOXYLIC ACID + MgBrCl (+1C = the addition of one Carbon molecule to the chain) ii. GRIGNARD + METHANAL → (+1C) 1º ALCOHOL + MgBrCl iii. GRIGNARD + Other ALDEHYDES → (+1C) 2º ALCOHOL +MgBrCl iv. GRIGNARD + KETONE → (+1C)3º ALCOHOL + MgBrCl • Reagents and Conditions: 1) Dry Reagents 2) With HCl2. CARBOXYLIC ACIDS Preparation: i. 1º ALCOHOLS + 2[O] → CARBOXYLIC ACID + WATER • Reagents and Conditions: 1) Heat under Reflux 2) Potassium Dichromate / H2SO4 ii. Hydrolysis of Nitriles NITRILE + 2H2O + HCl → CARBOXYLIC ACID + NH4Cl • Reagents and Conditions: 1) Heat under reflux 2) With dilute HCl Reactions: i. CARBOXYLIC ACID + NaOH → CARBOXYLATE SALT + H2O ii. CARBOXYLIC ACID + Na2CO3/NaHCO3 → CARBOXYLATE SALT + H2O + CO2 iii. CARBOXYLIC ACID + ALCOHOL ↔ ESTER + H2O • Reagents and Conditions: 1) Warmed under reflux 2) With concentrated H2SO4 iv. CARBOXYLIC ACID + PCl5 → ACID CHLORIDE + POCl3 + HCl • Reagents and Conditions: 1) Dry / room temperature v. CARBOXYLIC ACID + 4[H] → ALCOHOL + H2O • Reagents and Conditions: 1) LiAlH4 in dry ether 2) With HCl3. ACID CHLORIDES: Preparation: i. CARBOXYLIC ACID + PCl5 → ACID CHLORIDE + HCl + POCl3 Reactions: i. ACID CHLORIDE + H2O → CARBOXYLIC ACID + HCl ii. ACID CHLORIDE + ALCOHOL → ESTER + HCl iii. ACID CHLORIDE + (concentrated)AMMONIA → AMIDE + NH4Cl iv. ACID CHLORIDE + AMINE → SUBSTITUTED AMIDE + HCl 1 of 3
  2. 2. 4. ESTERS: Preparation: i. CARBOXYLIC ACID + ALCOHOL ↔ ESTER + H2O • Reagents and Conditions: 1) Warmed under reflux 2) With concentrated H2SO4 ii. ACID CHLORIDE + ALCOHOL → ESTER + HCl Reactions: i. ESTER + NaOH → ALCOHOL + CARBOXYLATE SALT • Reagents and Conditions: 1) Heat under reflux ii. ESTER + H2O ↔ CARBOXYLIC ACID + ALCOHOL • Reagents and Conditions: 1) Warmed under reflux 2) With concentrated H2SO45. CARBONYL COMPOUNDS: Preparation – Aldehydes: i. 1º ALCOHOL + [O] → ALDEHYDE + H2O • Reagents and Conditions: 1) Heat under DISTILLATION 2) Potassium Dichromate / H2SO4 Preparation – Ketones: i. 2º ALCOHOL + [O] → KETONE + H2O • Reagents and Conditions: 1) Heat under reflux 2) Potassium Dichromate / H2SO4 Reactions – Both Aldehydes and Ketones: i. CARBONYL + 2,4-DNPH → YELLOW/ORANGE PPT. + H2O ii. Aldehyde + HCN → n-HYDROXY ALKYLNITRILE • Reagents and Conditions: 1) HCN / KCN in pH 8 buffer solution iii. Ketone + HCN → n-HYDROXY-n-METHYL ALKYLNITRILE • Reagents and Conditions: 1) HCN / KCN in pH 8 buffer solution iv. CARBONYL + 2[H] → ALCOHOL (Aldehyde = 1º / Ketone = 2º) • Reagents and Conditions: 1) LiAlH4 in dry ether v. CARBONYL + GRIGNARD → ALCOHOL (Methanal=1ºAld=2º/Ket=3º) + MgBrCl • Reagents and Conditions: 1) In dry ether 2) HCl Iodoform of Ethanal and Methyl Ketones (-COCH3): i. ETHANAL + 3I2 + 4NaOH → CHI3 + 3NaI + SODIUM METHANOATE + 3H2O ii. METHYL KETONE + 3I2 + 4NaOH → CHI3 + 3NaI + SODIUM CARBOXYLATE + 3H2O Reactions – Aldehydes ONLY: i. Aldehyde + [O] + OH- → RED PPT. + CARBOXYLATE SALT + H2O • Reagents and Conditions: 1) Warmed with Fehling’s Solution ii. Aldehyde + [O] + OH- → SILVER MIRROR + CARBOXYLATE SALT + H2O • Reagents and Conditions: 1) Warmed 2) With Silver Nitrate in dilute Ammonia 2 of 3
  3. 3. 6. 1º AMINES Preparation: i. NITRILE + 4[H] → AMINE • Reagents and Conditions: 1) LiAlH4 in dry ether ii. HALOALKANE + NH3 → AMINE + HX • Reagents and Conditions: 1) Heated in a sealed tube 2) Concentrated NH3 Reactions – With ACIDS i. AMINE + HCl → ALKYL AMMONIUM+CHLORIDE- ii. AMINE + CH3COOH → ALKYL AMMONIUM ETHANOATE Reactions – With ACID CHLORIDES i. AMINE + ACID CHLORIDE → SUBSTITUTED AMIDE + HCl7. NITRILES Preparation: i. HALOALKANE + KCN → (+1C)NITRILE + KX • Reagents and Conditions: 1) Heat under reflux 2) Aqueous Ethanol ii. CARBONYL + HCN → HYDROXY NITRILE • Reagents and Conditions: 1) HCN / KCN in pH 8 buffer solution Reactions: i. NITRILE + H+ + 2H2O → CARBOXYLIC ACID + AMMONIUM+ (hydrolysis) • Reagents and Conditions: 1) Heat under reflux 2) With acid / HCl ii. NITRILE + 4[H] → 1º AMINE • Reagents and Conditions: 1) LiAlH4 in dry ether8. AMIDES: Preparation: i. ACID CHLORIDE + NH3 → AMIDE + HCl ii. ACID CHLORIDE + AMINE → AMIDE– R + HCl Reactions: i. Dehydration: 6AMIDE + P4O10 → 6NITRILE + 4H3PO4 Simplified: AMIDE - H2O → NITRILE • Reagents and Conditions: 1) With warm P4O10 ii. Hoffman’s Degradation: AMIDE + Br2 + 4NaOH → (-1C) AMINE + Na2CO3 + 2NaBr + 2H2O Simplified: RCONH2 → RNH2 • Reagents and Conditions: 1) Warmed under DISTILLATION 2) Br2 / NaOH9. AMINO ACIDS: Reactions: i. With Acids: NH2CH2COOH + H+ → NH3+CH2COOH 3 of 3
  4. 4. ii. With Bases: NH2CH2COOH + OH- → NH2CH2COO- + H2O 4 of 3

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