Organic 2 Section 3 - Unit 26: Compounds containing the carbonyl groups
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Explain why ethanoyl chloride reacts readily with nucleophiles. Write an equation for one nucleophilic addition–elimination reaction of ethanoyl chloride (4 marks)
• Large charge on carbonyl carbon atom due to bonding to O and Cl • Nucleophiles have electron pairs which can be donated • CH3COCl (l) + CH3CH2OH → CH3CO2CH2CH3 + HCl (g)
Oxidation of aldehydes (3): • Product • Reagent • Conditions
• Carboxylic Acid • Potassium dichromate and dilute sulfuric acid • Heat under reflux
Reduction of carbonyls (3): • Product • Reagent • Conditions
• Alcohol • NaBH4 in aqueous ethanol • Room temperature and pressure
Addition of hydrogen cyanide to carbonyls (4): • Mechanism • Product • Reagent • Condition
• Nucleophilic addition • Hydroxynitrile • Sodium cyanide and dilute sulfuric acid • Room temperature and pressure
Write an overall equation for the reduction of butanone using [H] to represent the reductant (1 mark)
• CH3CH2COCH3 + 2[H] → CH3CH2CH(OH)CH3
Give one advantage of the use of propanoyl chloride instead of propanoic acid in the laboratory preparation of methyl propanoate from methanol (1 mark)
• Faster • Irreversible • Bigger yield • Purer product • No acid catalyst required
Give one advantage of the use of propanoic anhydride instead of propanoyl chloride in the laboratory preparation of methyl propanoate from methanol (1 mark)
• Anhydride less easily hydrolysed - Reaction less exothermic
Acyl chloride → carboxylic acid (2) • Reagent • Conditions
• Water - Room Temperature
Acid Anhydride → carboxylic acid (2) • Reagent • Conditions
• Water - Room Temperature
Acyl chloride → ester (2) • Reagent • Conditions
• Alcohol - Room Temperature
Acid Anhydride → ester (2) • Reagent • Conditions
• Alcohol - Room Temperature
Acyl chloride → primary amide (2) • Reagent • Conditions
• Ammonia - Room Temperature
Acid Anhydride → Primary amide (2) • Reagent • Conditions
• Ammonia - Room Temperature
Acyl chloride → secondary amide (2) • Reagent • Conditions
• Primary amine - Room Temperature
Acid Anhydride → secondary amide (2) • Reagent • Conditions
• Primary amine - Room Temperature
State two observations, during the determination of melting point that would indicate that a sample of aspirin is not pure (2 marks)
• Melting point range would be wide - And below the true melting point
Give one advantage and one disadvantage of preparing ethyl ethanoate by the reaction of carboxylic acid + alcohol rather than acyl chloride and alcohol (2 marks)
Advantages: - Reaction goes to completion, not reversible or faster Disadvantages: - Reaction vigorous/dangerous or HCl is toxic
Explain why butylamine is a stronger base than ammonia (2 marks)
• Lone pair (on N) (in correct context) - R group increases electron density / donates electrons
What sort of a reaction is Tollens’ reagent (1 mark)
• Redox reaction
Explain why ethanoyl chloride reacts readily with nucleophiles (2 marks)
• Large charge on carbonyl carbon atom due to bonding to O and Cl • Nucleophiles have electron pairs which can be donated
Reagents for oxidation (1 mark)
Potassium dichromate
Reagents and conditions for nucleophilic addition (2 marks)
• NaBH4 - In methanol or water
Reagents and conditions for esterification (3 marks)
• Concentrated H2SO4 • Heat under reflux • Warm
State one use of methyl esters (1 mark)
Biodiesel