Synthesis of Aspirin

Question 1

chemical name of aspirin

Answer 1

acetylsalicylic acid

Question 2

widely used as an analgesic, anti-inflammatory, and anti-pyretic medicine

Answer 2

aspirin

Question 3

drug acting to relieve pain

Answer 3

analgesic

Question 4

drug used to prevent or reduce fever

Answer 4

antipyretic

Question 5

starting material used in the synthesis of aspirin has been used as a pain reliever in many ancient cultures

Answer 5

salicylic

Question 6

where salicylic was first extracted

Answer 6

willow tree bark

Question 7

apsirin will be synthesized using

Answer 7

salicylic acid
anhydride
phosphoric acid

Question 8

draw the mechanism for the creation of aspirin using salicylic acid and acetic anhydride

Answer 8

grade yourself accordingly

Question 9

phosphoric acid

Answer 9

H3PO4

Question 10

structure of acetylsalicylic acid

Answer 10

grade yourself accordingly

Question 11

formula for percentage yield

Answer 11

actual yield/theoretical yield *100

Question 12

test to be done other than computing for the percentage yield

Answer 12

melting point determination and FeCl3 test

Question 13

carboxylic acid derivatives where the -OH group of the carboxylic acid is replaced by an -OR

Answer 13

Esters

Question 14

produces ester from carboxylic acid and alcohol

Answer 14

esterification

Question 15

have characteristic pleasant odors and is usually the major component of flavors of certain fruits

Answer 15

esters

Question 16

the inability of esters to form H-bonding with other esters explain this characteristic compared to alcohols of similar MW

Answer 16

relatively lower boiling point

Question 17

esters cannot do this kind of bonding with fellow esters

Answer 17

h-bonding

Question 18

can form H-bonding with oxygen of esters, making low MW esters soluble in them

Answer 18

water

Question 19

hydrolyzed to produced salicylic acid and acetic acid

Answer 19

aspirin

Question 20

produced when aspirin is ingested

Answer 20

salicylic acid and acetic acid

Question 21

active ingredient in aspirin and the one responsible for blocking the synthesis of prostaglandins

Answer 21

salicylic acid

Question 22

molecules that at abnormally high levels can cause pain, inflammation, and fever

Answer 22

prostaglandins

Question 23

where aspirin may be synthesized from

Answer 23

salicylic acid
acetic anhydride

Question 24

used as a catalyst in producing aspirin

Answer 24

phosphoric acid

Question 25

materials needed for esterification

Answer 25

Salicylic acid Acetic acid Methanol Ethanol Isoamyl alcohol Benzoic acid Conc. Sulfuric acid Aluminum foil

Question 26

material needed for aspirin synthesis

Answer 26

Acetylsalicylic acid Phosphoric acid Acetic anhydride Distilled water

Question 27

equipment needed

Answer 27

Test tube Hot plate Thermometer Melting point apparatus Vacuum filtration set-up Filter paper Top loading balance

Question 28

how much carboxylic acid and alcohol is needed for esterification test

Answer 28

2 mL -carboxylic acid 4 mL - alcohol

Question 29

pairings of carboxylic acid and alcohol

Answer 29

Glacial acetic acid – ethanol Salicylic acid – methanol Benzoic acid – isoamyl alcohol

Question 30

what is added with carboxylic acid and alcohol for esterification

Answer 30

H2SO4

Question 31

how long and how high the temperature for the water bath in esterification

Answer 31

5 minutes (40-50 degrees)

Question 32

procedure of aspirin synthesis: 1. how much salicylic acid is needed

Answer 32

1.10g

Question 33

how many drops and how much concentration of H3PO4

Answer 33

8 drops of 85% phosphoric acid

Question 34

how much acetic anhydride is needed

Answer 34

2.4mL

Question 35

how long and how high the temp in water bath for aspirin synthesis

Answer 35

5 minutes 90 degrees celsius

Question 36

how much water is added

Answer 36

1.6 mL

Question 37

where will the erlenmeyer flask be placed when there is no crystallization

Answer 37

ice bath

Question 38

odor produced when acetic acid and ethanol is reacted together

Answer 38

plastic balloon

Question 39

odor produced when salicylic acid and methanol is reacted together

Answer 39

vanilla

Question 40

odor produced when benzoic acid and isoamyl alcohol is reacted together

Answer 40

white board marker ink

Question 41

what forms when ethyl alcohol and acetic acid reacts with the presence of H2SO4

Answer 41

ethyl acetate

Question 42

– formed when methyl alcohol and salicylic acid reacts with H2SO4

Answer 42

methyl salicylate

Question 43

formed when isoamyl alcohol and benzoic acid reacts with sulfuric acid

Answer 43

isoamyl benzoate

Question 44

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

Answer 44

phosphoric acid

Question 45

the carbonyl oxygen undergo this process of the acetic anhydride, making it more reactive

Answer 45

protonation

Question 46

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

Answer 46

90 degrees

Question 47

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

Answer 47

ice bath

Question 48

enzyme that aspirin inhibits

Answer 48

cyclooxygenase

Question 49

where COX is inhibited by the aspirin to function as an analgesic

Answer 49

peripheral tissues

Question 50

where COX is inhibited to reduce fever

Answer 50

hypothalamus

Question 51

draw the reaction of acetic acid and ethanol

Answer 51

grade yourself accordingly

Question 52

draw the reaction of salicylic acid and methanol

Answer 52

grade yourself accordingly

Question 53

draw the reaction of benzoic acid and isoamyl alcohol

Answer 53

grade yourself accordingly

Question 54

study the mechanism of aspirin synthesis

Answer 54

explain it through whiteboard/feymann