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Inorganic and Organic Chemistry > Synthesis of Aspirin > Flashcards

Synthesis of Aspirin Flashcards

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1
Q

chemical name of aspirin

A

acetylsalicylic acid

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2
Q

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

A

aspirin

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3
Q

drug acting to relieve pain

A

analgesic

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4
Q

drug used to prevent or reduce fever

A

antipyretic

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5
Q

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

A

salicylic

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6
Q

where salicylic was first extracted

A

willow tree bark

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7
Q

apsirin will be synthesized using

A

salicylic acid
anhydride
phosphoric acid

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8
Q

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

A

grade yourself accordingly

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9
Q

phosphoric acid

A

H3PO4

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10
Q

structure of acetylsalicylic acid

A

grade yourself accordingly

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11
Q

formula for percentage yield

A

actual yield/theoretical yield *100

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12
Q

test to be done other than computing for the percentage yield

A

melting point determination and FeCl3 test

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13
Q

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

A

Esters

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14
Q

produces ester from carboxylic acid and alcohol

A

esterification

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15
Q

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

A

esters

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16
Q

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

A

relatively lower boiling point

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17
Q

esters cannot do this kind of bonding with fellow esters

A

h-bonding

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18
Q

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

A

water

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19
Q

hydrolyzed to produced salicylic acid and acetic acid

A

aspirin

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20
Q

produced when aspirin is ingested

A

salicylic acid and acetic acid

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21
Q

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

A

salicylic acid

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22
Q

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

A

prostaglandins

23
Q

where aspirin may be synthesized from

A

salicylic acid
acetic anhydride

24
Q

used as a catalyst in producing aspirin

A

phosphoric acid

25
Q

materials needed for esterification

A

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

26
Q

material needed for aspirin synthesis

A

Acetylsalicylic acid
Phosphoric acid
Acetic anhydride
Distilled water

27
Q

equipment needed

A

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

28
Q

how much carboxylic acid and alcohol is needed for esterification test

A

2 mL -carboxylic acid
4 mL - alcohol

29
Q

pairings of carboxylic acid and alcohol

A

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

30
Q

what is added with carboxylic acid and alcohol for esterification

A

H2SO4

31
Q

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

A

5 minutes (40-50 degrees)

32
Q

procedure of aspirin synthesis:

  1. how much salicylic acid is needed
A

1.10g

33
Q

how many drops and how much concentration of H3PO4

A

8 drops of 85% phosphoric acid

34
Q

how much acetic anhydride is needed

A

2.4mL

35
Q

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

A

5 minutes 90 degrees celsius

36
Q

how much water is added

A

1.6 mL

37
Q

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

A

ice bath

38
Q

odor produced when acetic acid and ethanol is reacted together

A

plastic balloon

39
Q

odor produced when salicylic acid and methanol is reacted together

A

vanilla

40
Q

odor produced when benzoic acid and isoamyl alcohol is reacted together

A

white board marker ink

41
Q

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

A

ethyl acetate

42
Q

– formed when methyl alcohol and salicylic acid reacts with H2SO4

A

methyl salicylate

43
Q

formed when isoamyl alcohol and benzoic acid reacts with sulfuric acid

A

isoamyl benzoate

44
Q

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

A

phosphoric acid

45
Q

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

A

protonation

46
Q

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

A

90 degrees

47
Q

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

A

ice bath

48
Q

enzyme that aspirin inhibits

A

cyclooxygenase

49
Q

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

A

peripheral tissues

50
Q

where COX is inhibited to reduce fever

A

hypothalamus

51
Q

draw the reaction of acetic acid and ethanol

A

grade yourself accordingly

52
Q

draw the reaction of salicylic acid and methanol

A

grade yourself accordingly

53
Q

draw the reaction of benzoic acid and isoamyl alcohol

A

grade yourself accordingly

54
Q

study the mechanism of aspirin synthesis

A

explain it through whiteboard/feymann

Inorganic and Organic Chemistry (19 decks)

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