Carbonyls and Carboxylic Acids and their Derivatives Flashcards
Catalyst for formation of esters from alcohol + COOH
Conc acid eg. H2SO4
Catalyst for hydrolysis of esters
Dilute strong acid eg. Dilute H2SO4
Advantages of base hydrolysis
Reaction goes to completion due to neutralisation by base, more product in the mixture than by acid hydrolysis
Uses of glycerol and sodium salts
Soaps and cleaning products
Acid + metal —>
Salt + hydrogen
Acid + alkali —>
Salt + water
Acid + carbonate —>
Salt + water + CO2
Uses of esters (4)
Perfumes, flavourings, solvents, plasticisers for polymers
Are esters soluble or insoluble in water
Almost insoluble
Conditions for acid hydrolysis
Dilute acid, heat under reflux
Conditions for base hydrolysis
Dilute NaOH, heat under reflux
Products of base hydrolysis
Carboxylate salt + alcohol
Why isn’t base hydrolysis reversible
The carboxylate salt is the anion of the COOH, the anion is resistant to attack by weak nucleophiles eg. alcohols so it’s not reversible
Uses of glycerol
Soluble in water so good in cosmetics, food and glues
How does soap work
The polar CO2 - end is hydrophilic and mixes with water, the long non- polar hydrocarbon chain is hydrophobic and mixes with grease. So grease and water can mix and be washed away
Catalyst for vegetable oils + methanol —> biodiesel
Strong alkali catalyst
Vegetable oil + methanol —>
Biodiesel
Which is more reactive acyl chlorides or COOH
Acyl chlorides
Acyl chloride + water —>
COOH + HCl
Reagent and conditions for Acyl chloride + water
Water, room temp
Acid anhydride + water —>
COOH
Reagent and conditions for acid anhydride + water
Water, room temp
What type of mechanism is acyl chloride + water
Nucleophilic addition elimination
Acyl chloride + alcohol —>
Ester + HCl
Reagent and condition for acyl chloride + alcohol
Alcohol, room temp
Observation for Acyl chloride + water
Steamy white fumes of HCl
Observation for Acyl chloride + alcohol
Steamy white fumes of HCl
Acyl chloride + ammonia —>
Amide + HCl
Reagent and conditions for Acyl chloride + ammonia
Ammonia, room temp
Acyl chloride + amine —>
N-substituted amide + HCl
Observation for acyl chloride + ammonia
White smoke of NH4Cl
Acid anhydride + alcohol —>
Ester + COOH
Reagents and conditions for acid anhydride + alcohol
Room temp, alcohol
Acid anhydride + ammonia —>
Amide + COOH
Reagent and conditions for Acid anhydride + ammonia
Ammonia, room temp
Acid anhydride + primary amine —>
N- substituted amide + COOH
Reagent and conditions for acid anhydride + amine
Amine, room temp
In the production of aspirin why is the minimum volume of hot solvent used
To obtain a saturated solution and to enable crystallisation on cooling
What reasons are there for a loss of yield in the production of aspirin (3)
Crystals lost when filtering/ washing
Some product stays in the solution after recrystallisation
Other side reactions occur
What happens to the MP if impurities are present
The MP will be lower and it will melt over a range of degrees
Ethanoic anhydride is chosen over ethanoyl chloride for the production of aspirin, why?
Doesn’t produce toxic HCl
Doesn’t have to be anhydrous so cheaper
The by product (ethanoic acid) can react further to give more product
Why isn’t ethanoic acid used in the production of aspirin
Ethanoyl chloride and ethanoic anhydride are faster and produce higher yields
Reagent for the formation of a hydroxynitrile
HCN or a mix of KCN and HCN
What type of reaction is the formation of a hydroxynitrile
Nucleophilic addition
What reagent is needed to reduce an aldehyde
NaBH4 dissolved in methanol and water
What is an aldehyde reduced to
A primary alcohol
What are ketones reduced to
Secondary alcohols
What are advantages of biodiesels
Renewable
Less CO2
Fewer pollutants
Non- toxic
Advantages of using methyl esters over triglycerides as fuels in car engines
They don’t have glycerol in so it doesn’t make carbon depositions of pistons
They’re less viscous
More reliable in cold winter
What type of reaction reduces aldehydes and ketones to alcohols
Nucleophilic addition