Synthesis of Aspirin Flashcards
chemical name of aspirin
acetylsalicylic acid
widely used as an analgesic, anti-inflammatory, and anti-pyretic medicine
aspirin
drug acting to relieve pain
analgesic
drug used to prevent or reduce fever
antipyretic
starting material used in the synthesis of aspirin has been used as a pain reliever in many ancient cultures
salicylic
where salicylic was first extracted
willow tree bark
apsirin will be synthesized using
salicylic acid
anhydride
phosphoric acid
draw the mechanism for the creation of aspirin using salicylic acid and acetic anhydride
grade yourself accordingly
phosphoric acid
H3PO4
structure of acetylsalicylic acid
grade yourself accordingly
formula for percentage yield
actual yield/theoretical yield *100
test to be done other than computing for the percentage yield
melting point determination and FeCl3 test
carboxylic acid derivatives where the -OH group of the carboxylic acid is replaced by an -OR
Esters
produces ester from carboxylic acid and alcohol
esterification
have characteristic pleasant odors and is usually the major component of flavors of certain fruits
esters
the inability of esters to form H-bonding with other esters explain this characteristic compared to alcohols of similar MW
relatively lower boiling point
esters cannot do this kind of bonding with fellow esters
h-bonding
can form H-bonding with oxygen of esters, making low MW esters soluble in them
water
hydrolyzed to produced salicylic acid and acetic acid
aspirin
produced when aspirin is ingested
salicylic acid and acetic acid
active ingredient in aspirin and the one responsible for blocking the synthesis of prostaglandins
salicylic acid
molecules that at abnormally high levels can cause pain, inflammation, and fever
prostaglandins
where aspirin may be synthesized from
salicylic acid
acetic anhydride
used as a catalyst in producing aspirin
phosphoric acid
materials needed for esterification
Salicylic acid
Acetic acid
Methanol
Ethanol
Isoamyl alcohol
Benzoic acid
Conc. Sulfuric acid
Aluminum foil
material needed for aspirin synthesis
Acetylsalicylic acid
Phosphoric acid
Acetic anhydride
Distilled water
equipment needed
Test tube
Hot plate
Thermometer
Melting point apparatus
Vacuum filtration set-up
Filter paper
Top loading balance
how much carboxylic acid and alcohol is needed for esterification test
2 mL -carboxylic acid
4 mL - alcohol
pairings of carboxylic acid and alcohol
Glacial acetic acid – ethanol
Salicylic acid – methanol
Benzoic acid – isoamyl alcohol
what is added with carboxylic acid and alcohol for esterification
H2SO4
how long and how high the temperature for the water bath in esterification
5 minutes (40-50 degrees)
procedure of aspirin synthesis:
- how much salicylic acid is needed
1.10g
how many drops and how much concentration of H3PO4
8 drops of 85% phosphoric acid
how much acetic anhydride is needed
2.4mL
how long and how high the temp in water bath for aspirin synthesis
5 minutes 90 degrees celsius
how much water is added
1.6 mL
where will the erlenmeyer flask be placed when there is no crystallization
ice bath
odor produced when acetic acid and ethanol is reacted together
plastic balloon
odor produced when salicylic acid and methanol is reacted together
vanilla
odor produced when benzoic acid and isoamyl alcohol is reacted together
white board marker ink
what forms when ethyl alcohol and acetic acid reacts with the presence of H2SO4
ethyl acetate
– formed when methyl alcohol and salicylic acid reacts with H2SO4
methyl salicylate
formed when isoamyl alcohol and benzoic acid reacts with sulfuric acid
isoamyl benzoate
acts as a catalyst in the synthesis of aspirin by speeding up the reaction rate and facilitates the conversion of salicylic acid into acetyl salicylic acid
phosphoric acid
the carbonyl oxygen undergo this process of the acetic anhydride, making it more reactive
protonation
temperature of water bath to allow the reaction to proceed at a reasonable rate, both speeding up the reaction rate and allowing for efficient conversion of salicylic acid into acetyl salicylic acid
90 degrees
placing the mixture in this cools down the reaction mixture to stop the reaction and prevent and side reactions to maximize the amount of crystals
ice bath
enzyme that aspirin inhibits
cyclooxygenase
where COX is inhibited by the aspirin to function as an analgesic
peripheral tissues
where COX is inhibited to reduce fever
hypothalamus
draw the reaction of acetic acid and ethanol
grade yourself accordingly
draw the reaction of salicylic acid and methanol
grade yourself accordingly
draw the reaction of benzoic acid and isoamyl alcohol
grade yourself accordingly
study the mechanism of aspirin synthesis
explain it through whiteboard/feymann