MID-TERM : ORGANIC CHEMISTRY LABORATORY

#LAB 1 : Melting point determination:

 melting point: point at which solid and liquid phases are in equilibrium

Why should samples for melting point determination be finely powdered?

 Supply maximum area to react

 Provide an even distribution of heat into the reaction.

How does presence of impurities affect the melting point?

 Lower the observed melting point

 Melting to occur over a broader range of temperatures

What technique did you use for melting point

 Capillary method: placing a little of the sample in the bottom of a narrow capillary
tube that has been sealed at one end. The determination is made using a Melting
Point Apparatus that simultaneously heats both the sample tube and a thermometer.
The temperature range, over which the sample is observed to melt, is recorded. Some
pure materials have a very narrow melting range, perhaps as little as 0.5–1.0 °C, while
more typically a 2–3 °C range is observed.
 The rate of heating, controlled by a dial, should be kept relatively low (a low melting
point)

Melting Points and Molecular Structure

 Melting points do generally increase with increasing molecular weight

 Factors play a role in determining melting points :

+ molecular shape, interactions between groups within the molecule

+ the degrees of freedom the molecule possesses within the crystal

#LAB2: Recrystallization

 4 charactersitics of a good solvent:

+ soluble at high temperatures + impurities are soluble at room temperature

+volatile + chemically inert

compound be soluble in the hot solvent but insoluble when the solvent is cold.

The impurities are either insoluble in the solvent at all temperatures or remain at least
moderately soluble in the cold solvent
  The processing of Recrystallization
1. Choosing the solvent

A solvent should be rejected if: the material appears readily soluble in the cold solvent, is
not soluble to any appreciable extent in the hot solvent even when the volume of solvent is
increased, or requires an impractically large volume in order to fully dissolve the crystals.

(Nên loại bỏ dung môi nếu: vật liệu có vẻ dễ hòa tan trong dung môi lạnh, không tan trong
bất kỳ mức độ đáng kể nào trong dung môi nóng ngay cả khi thể tích dung môi tăng, hoặc
cần một thể tích lớn để hòa tan hoàn toàn các tinh thể.)

2. Dissolving the sample ( using less solvent at this stage is advisable)

3. Hot filtration : gravity filtration is used to collect or isolate insoluble impurities from
solution
4. Cooling: Forming crystal formation
5. Cold filtration: Crystal collected by Suction Filtration
6. Washing the crystals : by ice-cold solvent
 Remove final soluble impurities
 Minimize losses the crystals redissolving
7. Drying the crystals
 Last trace of volatile solvent to evaporate

Explain:

Suction Filtration : Ring stand with clamp attached to filtration flask; rubber hose connected to
flas; neoprene adapter to help with proper filtration; Buchner funnel on top with slightly wet
filter paper so that it sticks  Transfer the last of the crystalline material

(Lọ c hú t: Giá đỡ vò ng có kẹp gắ n và o bình lọ c; ố ng cao su kết nố i vớ i flas; bộ chuyển đổ i

neoprene để giú p lọ c thích hợ p; Phễu Buchner ở trên cù ng vớ i giấ y lọ c hơi ướ t để nó dính
Chuyển phầ n cuố i cù ng củ a vậ t liệu kết tinh)

 If crystals don't form what happened?

 Too much solvent, have to boil it off and try recrystallizing (should have used minimum
amount of solvent)

% Recovered = Weight of benzoic acid obtained after recrystallization / Weight of

benzoic acid before recrystallization x 100

 Why are crystals washed with additional solvent when collected? Why cold solvent?

+ To removed impurities that are soluble in your solvent

+ https://www.coursehero.com/file/p61o7i8/o-You-MUST-wash-crystals-with-ice-cold-
solvent-to-minimize-crystals-dissolving/

#LAB 3: THIN LAYER CHOMATOGRAPHY

 Thin layer chromatography: solid-liquid technique , separation based on compounds

affinity for stationary phase and mobile phase
 This solvent is drawn up by capillary action
Common uses of Thin-Layer Chromatography:
1. To determine the number of components in a mixture.
2. To determine the identity of two substances.
3. To monitor the progress of a reaction

+ solid stationary phase: silica gel and alumina

+ mobile liquid phase : low bp organic solvents (mixture)

 The solvent level must be ensured to stay below that of the spot.

Retention Factor (Rf) : The difference each molecule travels along the adsorbent in relation to
how far the mobile phase has traveled and can be used to identify molecules.

The higher the Rf value, the less polar the compound.

 a less polar molecule will spend more time in the mobile phase and will therefore
move up the plate more quickly
 The more polar a molecule, the higher affinity it will have for the more polar silica
plate and will therefore spend less time in the mobile phase. As a result, it will move
up the plate more slowly
 depends on interaction with solid phase and polarity in relation to solvent system

 What would happen if origin line is so low that it gets covered by solvent/ eluent
 The chemicals and compounds put on the plate would get smeared across plate
 What would happen if you put too much of a compound on the origin line with the
capillary tube.
 Separation between different spots would be blurred. This would stop Rf from being
able to be calculated because could only get one, erroneous Rf value instead of 2
 TLC monitor the progress of a reaction: The increasing formation of products will cause
those spots to be more intense and others less intense

Visualization
  If the components of the sample are not colored, an Ultra–violet (UV)
lamp may reveal the location of the spots and their positions may then be marked with
a pencil
 the staining of a TLC plate with iodine vapor

# LAB 4 : COLUMN CHROMATOGRAPHY

+ Separate mixtures of materials

+ isolate large amounts of the individual components in pure form

Compare: COLUMN CHROMATOGRAPHY & TLC

SAME:

+ The stationary phase will be silica gel

+ the mobile phase will be a solvent, or mixture of solvents.

HOWEVER:

 The components of a mixture were separated from top to bottom using capillary
forces to draw solvent onto the bottom of a TLC plate.
 column chromatography is performed using gravity to draw solvent downward through
a glass tube containing the silica gel

Best solvent for column chromatography: run a bunch of trial columns

Column chromatography allows separation of relatively large amounts of a product

mixture into pure individual compounds, each of which can be isolated, characterized,
and perhaps used for other experiments or syntheses.

#LAB 5 Simple Distilation

 The vaporization of a liquid, relocation, and condensation of the resulting vapor is the
basis for a method of purification called distillation
 The temperature stabilizes at the boiling point and most of the liquid distills. The
temperature drops when there is no liquid left in the distillation flask.

+ Volatile impurities are the first compounds to distil- fore-run

+ Impurities that are higher boiling than the desired material are general not distilled

 If higher-boiling impurities are present in large quantities, the temperature may rise
from the desired level as the impurities begin to distil.
 the temperature frequently drops after the main fractions have distilled. If the
temperature drops at the end of a distillation, the last temperature to record is the
highest temperature, before the drop occurred.
 A too rapid rate leads to a lack of separation of components and also to uncondensed
vapor being carried through the condenser and into the room. It is generally necessary
to increase the amount of heat applied to the distillation flask (by increasing the
rheostat setting) during the course of a distillation.
Step

+ check the water flow through the condenser and make sure that all ground-glass joints are
snug.

+ Slowly heat the mixture in the distilling flask to a gentle boil (the
temperature reading on the thermometer will rise rapidly until it registers the initial boiling
point, which should be recorded)