So we meet again.

In the event you find this near sunrise filled with anxiety, rage and confusion I
hope this gives you a hand.
Purpose:
The purpose of this experiment was to perform a base-catalyzed hydrolysis reaction while
converting oil of wintergreen to salicylic acid. The full balanced molecular equation for the salicylic
acid synthesis is
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% & 'a#" % "
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illustrated equation showing compounds to be isolated or synthesized is shown below.

Salicylic Acid is a white crystalline compound with a melting point of ,*- and molecular weigh
of ,$! grams.mole, it is not symmetrical and typically gives / diff -,$ 'uclear 0agnetic
1esonance Signals.
Methyl salicylate has a relatively wea2 phenol and carboxylic functional groups that are important
in this experiment3 it also has a mint li2e smell smell, and reacts rapidly with 'a#". The -,$
'01 has extra signal compared to that of Salicylic +cid, a melting point of &&$, a molecular
weight of ,4& grams.mole and a density of ,.,/ g.m5. Structures of molecules mentioned above
are shown below.
Procedure
+ll procedures were carried out under a hood, all individuals involved wore nitrile gloves
and safety goggles. 6lassware was cleaned, rinsed with deionzed water and if necessary acetone
before usage. 1emember...be safe.
7irst $.4 m5 of water were poured into a 4-m5 round bottom flas2. 'ext .((! g Sodium
"ydroxide 8'a#"9, which happened to be in pellet form, was then weighed out using a weigh boat
and was added to the water, which was then swirled until the solid dissolved. The pellet form of the
'a#" made it difficult to acquire the .(! grams indicated by the manual. +fter the pellets dissolved
.&$ m5 of 0ethyl salicylate 8measured with a graduated pipette9 was added to the 'a#" solution.
+ boiling stone was then dropped to the bottom of the round bottom flas2.
'ext, using grease on the glass :oint, a water :ac2eted condenser was added to the round
bottom flas2. They were connected and held in place by a screw cap at the :oint of intersection
between the two. Two water tubes were attached to the condenser, the top arm attached to a tube
allowing for water to go out, the bottom arm of the condenser was connected to a tube lead from the
water source in the hood, allowing for the water to come in and run through. + clamp was used to
hold the apparatus steady and hold fast to a vertical rod in the hood. The round bottom flas2 was
2ept in place by an aluminum bloc2, placed on a heating plate, which was turned on to about ,.$ of
its maximum power. The mixture was heated for about ,4 minutes as the white solid dissolved.
+fter reflux, the equipment was allowed to cool to room temperature by separating it from
the heat source, it sat till it was only slightly warm and comfortable to handle. The condenser was
removed. 'ext, $0 Sulfuric +cid 8"&S#(9 was added in .4m5 increments till a white precipitate
formed and stayed as the solution continued to be stored. +n additional .4m5 were added to allow
completion of the precipitation reaction.
The contents of the round bottom flas2 then underwent vacuum filtration through a "irsch
7unnel fit with filter paper and connected with an integral adapter to a &4m5 filter flas2. The crude
product from the "irsch funnel was then transferred to weigh paper using a spatula. The salicylic
acid crystals were then placed in a ,-m5 ;rlenmeyer flas2. 'ext, 4m5 of water were added to the
;rlenmeyer flas2 containing the crystals. The solution was put on the hot plate till the solid
dissolved and was immediately ta2en off. The flas2 and its contents were allowed to sit at room
temperature while crystallization occurred. The crystals were collected via a second filtration using
a "irsch funnel with the same set up as the one done earlier in the experiment. <pon completion of
the filtration the crystals were placed in an empty vial and stored for a wee2. The following wee2
the crystals were pac2ed into a capillary tube with only one open side. The sample was placed in
apparatus, Mel Temp, that provided a magnified view of the sample and temperature, allowing for
the assessment of the samples melting point and range. +nother sample was prepared with acetone
with deutero "ydrogen by an instructor. This sample underwent -,$ 'uclear 0agnetic 1esonance
Spectroscopy 8-,$ '019. Samples from multiple lab groups ran through the machine, the goal
was to learn how the -,$ '01 helps determine molecular structure, and loo2 at the induced
magnetic field.
Things that are good to know for this lab:
7or 1eference=
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% & 'a#" % "
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7inding the limiting reagent 8plug and chug9
'ote= There is a ,=& molar ratio of 0ethyl salicylate 8
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9 to Sodium "ydroxide, respectively. 'ote,
0ethyl salicylate is the limiting reagent3 this will be used to calculate the theoretical yield.
>>>>> g 'a#" x , mole ? >>>>moles 'a#" x , mole 0ethylsalicylate ? .>>>> moles 0ethyl Salicylate needed
$@.@@ grams & moles 'a#"
>>> g 0ethyl Salicylate x , mole ? >>>> moles 0ethyl Salicylate x & moles 'a#" ? >>>> moles 'a#" needed
,4& grams , mole 0ethyl salicylate
Theoretical Yield: 1eferring to the balanced molecular equation there is a ,=, molar ratio
between 0ethyl Salicylate and the Salicylic +cid.
>>> moles 0ethyl Salicylate x , mole Salicylic +cid ? >>>> moles Salicylic acid expected
, mole 0ethyl Salicylate
>>>> moles Salicylic +cid expected x ,$! grams ? >>>> grams Salicylic +cid expected
, mole Salicylic +cid
Questions?
+fter '01 give two pieces of evidence that salicylic acid was the solid produced by reacting
methyl salicylate with the aqueous base. Ahich piece of evidence gives the direct structural
informationB Ahich gives only indirect evidenceB
,$ '01 of methyl salicylate has ! unique carbon pea2s, while salicylic acid has /. The that is
lost was bonded to & #xygen molecules ma2ing it down stream whihc is congruent with the
chemical equaiton. ,$ '01 gives indirect structural information.
0easuring the melting point and range allows you to compare it to the 2nown melting point of
salicylic acid telling you if the compound has the same melting point and if it has impurities.
Impurities cause a depression and increase in range. The larger the range the more impurities it has.
0easuring the melting point gives direct information.
Ahy is it that dilute sulfuric acid does not allow the reaction to proceed while concentrated sulfuric
acid doesB
Sulfuric +cid is used as a reaction catalyst. This means that you need to overcome an activation
energy to create the product. The dilute sulfuric acid does not have as fast and as high dissociation
as the higher concentration sulfuric acid, thus the reaction does not finalize because it does not
overcome the energy of activation.
#n the other hand....
Ahat is the purpose of adding concentrated sulfuric acid in the preparation of methyl salicylateB
Sulfuric acid is used in esterfication reactions as a catalyst.
Ahen methyl salicylate is prepared from salicylic acid and methanol, an #"- is the leaving group
from the salicylic acid. The presence of the acid provides a large amount of "% ions to stabilize the
leaving group to "&#, and speeds up the rate of the reaction.
Ahat are the structures of each of the following compounds
i)-The organic species present immediately after methyl salicylate is first added to the aqueous
sodium hydroxide solution and before heating.
ii)-The organic species present at the end of the reflux period :ust before the sulfuric acid is added.
iii)The organic compound present after the sulfuric acid is added.
5abel each as being soluble or insoluble in water at room temperature.
The 0ethyl Salicylate is the option CiCit is insoluble in water at room temperature.
The image shown after adding 'a#" but before "&S#( is the organic species present at the end of
the reflux period it is soluble in "&#. Salicylic acid, the product is not soluble in water 8"&#9
during room temperature.
!hat are the relati"e che#ical shifts in parts per #illion and their assign#ent on the Salicylic
Acid #olecule for $%& 'M()
1emember -,$ '01 loo2s at unique carbons. 7or more on -,$ '01 clic2 here.

Peak, ,
ppm Assignment
112.3 A
117.3 B
119.1 C
130.4 D
136.0 E
162.1 F
171.6 G