Carbonyl groups Flashcards
What is the carboxyl group?
COOH
What is the carboxyl group made up of?
carbonyl group and hydroxyl group
Why are carboxylic acids weak acids?
bc they dissociate partially
Why are short chain carboxylic acids soluble in water?
bc the carbonyl and hydroxyl group form hydrogen bonds with water bc theyre polar
Why aren’t long chain carboxylic acids soluble in water?
bc the hydrocarbon chain is non-polar so it cannot form hydrogen bonds with the water
why do carboxylic acids have a higher boiling point than alcohols?
bc of the polar carboxyl group, hydrogen bonds form between carboxylic acid molecules to form dimers which are double the size of acid molecules so increased van der Waals forces so higher bp
what is the metal salt of a carboxylic acid called?
carboxylate
how does an aqueous carboxylic acid dissociate in water?
RCOOH RCOO- + H+
how does a carboxylic acid react with water?
RCOOH + H2O —> RCOO- + H3O+
how does a carboxylic acid react with carbonates?
RCOOH + Na2CO3 —-> RCOONa + CO2 + H2O
carboxylic acid + carbonate –> ?
CO2 + H2O + RCOONa
what do you observe when you react a carboxylic acid with carbonate?
effervescence, a gas that turns limewater cloudy and also a colourless liquid remains
how do you test for a carboxylic acid?
add a carbonate and watch for effervescence and a gas that turns limewater cloudy
acid + metal —> ?
salt + hydrogen
what do you observe when an acid and metal react?
effervescence and colourless solution
acid + base —> ?
salt + water
what do you observe when an acid and base react?
heat and colourless solution
carboxylic acid + ammonia —>
ammonium carboxylate
what kind of reaction forms esters?
condensation reaction
what is produced when carboxylic acids and alcohols react?
ester and water are formed
name the four uses of esters
plasticisers, solvents, perfumes, food flavourings
by what processes are esters broken down?
hydrolysis
what does the acid hydrolysis of esters produce?
an equilibrium with carboxylic acids and alcohols
what are the conditions for acid hydrolysis?
heat under reflux with dilute hydrochloric acid
explain how alkaline hydrolysis of esters works
ester and alkali react to completely form carboxylate salt and alcohol. carboxylate further reacted with an acid to form carboxylic acid
what is a triglyceride?
an ester of propane-1,2,3-triol (glycerol) and fatty acid chains joined together by ester linkages
what is the chemical formula for glycerol?
propane-1,2,3-triol
what is saponification?
the alkaline hydrolysis of esters
what are soaps?
the salts produced by the saponification of triglycerides
what is the by-product of saponification of triglycerides and how is it used in industry?
glycerol can be used in cosmetics and pharmaceuticals
what is trans-esterification?
when you react an ester with an alcohol to produce a different ester and alcohol
when preparing an ester, why is sodium carbonate added to the crude ester?
to remove any unreacted acid and remove unreacted acid catalyst
when preparing an ester, why is calcium chloride added?
to remove any unreacted alcohol
by what process is biodiesel made?
transesterification
how is biodiesel made?
reacting triglycerides with methanol to form biodiesel and glycerol
what is biodiesel
methyl esters
acyl chloride + alcohol
ester + hydrogen chlorise
acid anyhydride + alcohol
ester and carboxylic acid
why is acid anhydride preferred over acyl chlorides to make esters?
no toxic HCl fumes made
cheaper
easier to control
acyl chloride + water
carboxylic acid + hydrogen chlorise
acid anhydride + water
carboxylic acid 1 + carboxylic acid 2
acyl chloride + ammonia
amide + ammonium chloride
acid anhydride + ammonia
amide + ammonium carboxylate
acid chloride + 2amine
N-substituted amide
alkyl ammonium chloride
acid anyhdride + 2amine
N substituted amide
salt
explain how to prepare and purify an ester
equimolar volumes of acid and alcohol in pear shaped flask
add H2So4 slowly with cooling
anti-bumping granules
distill and put into a separating funnel
add sodium carbonate and invert
separate layers and allow lower one to be removed
calcium chloride to remove alcohol
filter
redistil and collect at appropriate fraction
explain the recrystallisation process
dissolve impure product in the min volume of hot solvent
do gravity filtration of HOT solvent through fluted filter paper in a glass funnel
cool and crystallise
wash with water
suction filtration (press between filter papers for better drying)
why is the minimum volume of hot solvent used?
to ensure crystals form on cooling
so the solution is saturated
why is gravity filtration done with HOT solvent
so it doesnt crystallise during filtration
why do you do gravity filtration?
to remove insoluble impurities
why do you allow the solution to cool and form crystals?
lower temp = lower solubility so it removes soluble impurities
why do you compress the substance in the buchner funnel?
increased air flow through the substances