Carboxylic acids 3.3.9 Flashcards
Name three reactions to prepare carboxylic acids
Oxidation of primary alcohol under reflux
Oxidation of aldehyde under reflux
Hydrolysis of Nitriles
Describe the reaction (and write the equation) for hydrolysis of nitriles
Nitrile is refluxed with water and hydrochloric acid
Produces carboxylic acid and ammonium chloride
R-C≡N + 2H2O + HCl →RCOOH + NH4Cl
What happens when Carboxylic acids dissociate
Forms a carboxylate ion RCOO- (negative) and a H+ ion
Is dissociation of carboxylic acids reversible
yes
What is the charge of a carboxylate ion
Negative
Is the carboxylate ion stable or not - why?
Yes
Negative charge is delocalised across the whole carboxylate group
Give the products of the reaction of methanoic acid and sodium carbonate
Sodium methanoate. carbon dioxide and water
What is produced when coohs react with carbonates
Salt, water and CO2
What is produced when coohs are neutralised
Salt and water
What is produced when propanoic acid and sodium hydroxide are reacted together
Sodium propanoate and water
What is formed when an alcohol and carboxylic acid react
Ester and water
What is the functional group of an ester
COO
What type of reaction occurs when an alcohol and carboxylic acid react
Condensation
What are the products formed when propanoic acid reacts with methanol
Methyl prooanoate and water
What is hydrolysis of esters
Splitting up esters using water
What two types of hydrolysis are there
Base and Acid
What acids at what strength are used in acid hydorlysis
Dilute HCL or H2SO4
Ester+Water (with H+) =
OH and COOH
What does acid hydrolysis produce
Alcohol and cabroxylic acid
What does base hydrolysis producen
Carboxylate ion and alcohol
What is the IUPAC name of glycerol
propane-1,2,3-triol
In what way are fats and lipids esters of glyceorl
Glycerol (alcohol) reacts in a condensation to reaction with 3 fatty acids (COOH) to form fatty acids with COO
Do saturated fatty acids have double bonds C=C
NO
What is the difference between fats and oils and why
Fats are normally solids at room temperature but oils are liquids at room temperature
Because
Oils are polysaturated whereas fats are unsaturated
So
Molecules of fats get closer together as the chain DOES NOT bend so VdWs are stronger and so fats have a higher MP
How is soap formed
Hydrolysis of animal fats or vegetable oils (heated with NaOH)
What happens when you react a fat/oil with NaOH
It forms a sodium salt and glycerol
How is biodiesel made
React oils with methanol (KOH catalyst)
What is biodiesel actually
Methyl ester
What is formed when yiu react oils with methanol (KOH catalyst)
Glycerol and methyl ester
Functional group of acyl/acid chlorides
COCl
Why are COCls susceptible to attack by nuclepphiles
in cocl c=o and c-cl bonds are polar
What is the reaction called when COCls react with water, nh3 or amines
Addition-elimination
What is produced when COCl reacts wtih water
Carboxylic acid and HCl
What is produced when COCl reacts with NH3 nucleophile
alkyl amide + NH4Cl
What is produced when COCl reacts wtih alcohol
Ester + HCl
Amine vs Amide
Amine is MINE because its noT C=Ool
What is produced when acid anhydrides react with water
Carboxylic acid
What is produced when acid anhydrides react with alcohols
Ester and carboxylic acid
What is produced when acid anhydrides react with primary amines or NH3
Amides
Name The industrial advantages of ethanoic anhydride over ethanoyl chloride in the manufacture of the drug aspirin.
Ethanoic anhydride is cheaper than ethanoyl chloride.
Ethanoic anhydride is safer to use than ethanoyl chloride. It is less corrosive and not so readily hydrolysed (its reaction with water is slower).
Ethanoic anhydride doesn’t produce dangerous (corrosive and poisonous) fumes of hydrogen chloride
Describe how to purify a sample of aspirin
- Dissolve in minimum hot solvent
- Filter
-Cool in ice bath - Filter using buchner funnel
-Dry