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Spring

2017
Renan Gongora
Week Five: Crystallization
Disclaimer
The information provided here is to help facilitate learning and a
smoother in-lab experience but you need to read all procedures!!!

Furthermore, these are not complete procedures and all of the


procedure (unless modified should be followed per the lab manual, the
Pavia text, found on the appropriate pages indicated in the syllabus)

You will need to know Parts A and C for the quiz


You will perform Parts A and C in lab
Crystallization: Motivation
• A purification technique

• Based on solubility of
compounds at various
temperatures
Crystallization: Technique Experiment
• Background Theory
• You will have to use this for your lab reports (consequent preparative)
• You will need it for the quizzes
O OH
• Procedures O
• Part A O
• Part C H O
O OH O N OH
O

O
O
O
OH
Crystallization: Technique (Theory)

Thoroughly understand these concepts


Solubility
Polarity “like dissolves like”
Acid-base Chemistry
Percent recovery You will learn these techniques:
Crystallization
Vacuum Filtration
Melting Point (pure and impure solids)
Crystallization: Technique Experiment
• Background Theory
• You will have to use this for your lab reports (consequent preparative)
• You will need it for the quizzes
O OH
• Procedures O
• Part A O
• Part C H O
O OH O N OH
O

O
O
O
OH
Crystallization: Part A
Goal:
sulfanilamide
To dissolve impure sulfanilamide
in the minimum amount of hot
ethanol and then purify by
slowly crystallizing pure
fluorene (you’ve seen this)
sulfanilamide.

Calculate percent recovery!


Crystallization: Part A

Goal:
sulfanilamide
To dissolve impure sulfanilamide
in the minimum amount of hot
Use:
ethanol and then purify by
First generation of antibiotics for
slowly crystallizing pure
major diseases
sulfanilamide.
• Malaria
• Tuberculosis
• Leprosy
Crystallization: Part A

Goal:

To dissolve impure sulfanilamide


in the minimum amount of hot
ethanol and then purify by
slowly crystallizing pure
sulfanilamide.

Solubility curve vs. Temperature


Indicates that ethanol is a a suitable
solvent for crystallization
Why does the solubility curve end at 78ºC?

Crystallization: Part A

Goal:

To dissolve impure sulfanilamide


in the minimum amount of hot
ethanol and then purify by
slowly crystallizing pure
sulfanilamide.

Solubility curve vs. Temperature


Indicates that ethanol is a a suitable
solvent for crystallization
Crystallization: Part A

Goal:
sulfanilamide
To dissolve impure sulfanilamide
in the minimum amount of hot
Step 1) weigh 750 mg of
ethanol and then purify by
sulfanilamide and transfer to 50
slowly crystallizing pure
mL EF.
sulfanilamide.
Step 2) add 15 mL of ethanol
and a boiling stone

Step 3) warm to ≈70ºC


Crystallization: Part A
• Remove the flask from the heat and allow the solution to cool slowly
Goal: (see Technique 11, Section 11.3, Part C, for suggestions).

Crystallization should begin by the time the flask has cooled to room
To dissolve impure sulfanilamide • temperature. If it has not, scratch the inside surface of the flask with a
glass rod to induce crystallization (see Technique 11, Section 11.8).
in the minimum amount of hot • When it appears that no further crystallization is occurring at room
ethanol and then purify by temperature, place the flask in a beaker containing ice water (see
Technique 6, Section 6.9).
slowly crystallizing pure • Be sure that both water and ice are present and that the beaker is small
enough to prevent the flask from tipping over.
sulfanilamide. • Filtration. When crystallization is complete, vacuum filter the crystals
using a small Büchner funnel (see Technique 8, Section 8.3, and Figure
8.5). (If you will be performing the Optional Exercise at the end of this
procedure, you must save the mother liquor from this fil- tration
procedure. Therefore, the filter flask should be clean and dry.) Moisten
the filter paper with a few drops of 95% ethyl alcohol, and turn on the
vacuum (or aspirator) to the fullest
Crystallization: Part A • Use a spatula to dislodge the crystals from the bottom of the
flask before transferring the material to the Büchner funnel.
• Swirl the mixture in the flask and pour the mixture into the
funnel, attempting to transfer both crystals and solvent. You
will need to pour the mixture quickly, before the crystals have
completely resettled on the bottom of the flask. (You may
Goal: need to do this in portions, depending on the size of your
Büchner funnel.) When the liquid has passed through the
filter, repeat this procedure until you have transferred all the
liquid to the Büchner funnel.
To dissolve impure sulfanilamide • At this point, there will usually be some crystals remaining in
the flask. Using your spatula, scrape out as many of the
in the minimum amount of hot crystals as possible from the flask. Add about 2 mL of ice-cold
95% ethyl alcohol (measured with a calibrated Pasteur pipet)
ethanol and then purify by to the flask. Swirl the liquid in the flask and then pour the
remaining crystals and alcohol into the Büchner funnel..
slowly crystallizing pure • Continue drawing air through the crystals on the Büchner
funnel by suction for about 5 minutes. Transfer the crystals
sulfanilamide. onto a preweighed watch glass for air drying.
• Separate the crystals as much as possible with a spatula. The
crystals should be completely dried within 10–15 minutes.
You can usually determine if the crystals are still wet by
observing whether or not they stick to a spatula or stay
together in a clump. Weigh the dry crystals and calculate the
percentage recovery. Compare the color of the pure
sulfanilamide to the impure sulfanilamide at the beginning of
the experiment. Determine the melting point of the pure
sulfanilamide and the original impure material.
Crystallization: Part A (What to report)

Goal:

To dissolve impure sulfanilamide • Record the melting point of the final


in the minimum amount of hot crystals
ethanol and then purify by
• Record and calculate the percent
slowly crystallizing pure recovery
sulfanilamide.
Crystallization: Part C
Goal: To use the melting point apparatus to O OH

determine the identity and purity of an O

unknown from a list of unknowns. O

O H O
O OH N OH
Obtain the melting point of your unknown O

compound
O
O
O
OH
Crystallization: Part C (what to report)
O OH
Introduce the technique of O
crystallization, the most common
procedure used to purify crude solids in O

the organic lab. O OH O H


N
O
OH
O

Record the melting point of your sample


(pure or impure) O
O
Provide an identity of the unknown O
sample based off the melting point alone OH

(your choices are found in part C and are


drawn to the right on this slide)

State whether or not your compound is


pure or impure and why you obtained
that conclusion