Edited: 2/28/21

Lab Technique Review Worksheet

Due March 4th in the beginning of lab

Directions Answer the generic questions and specific questions for each of the five lab
techniques: melting point, recrystallization, distillation, extraction, TLC. You may need to use
your Padias textbook to review/learn the techniques. You will upload this assignment TWICE on
Canvas – once as a TurnItIn.com check and one for peer review.

For each of the five techniques, answer the following generic questions:
1) What is this technique typically used for? (purification, identification, determining purity,
etc.)
2) What is happening on the molecular level (talk about intermolecular forces) for each of
these techniques?

Melting Point
3) What two parts of melting point data do you look at to determine the purity of a
compound?
4) What is ramp rate and how does that affect a melting point measurement?
5) What is mixed melting point and what is it used for?

Applications:
6) You are trying to determine the melting point of an unknown compound. The unknown
has the possibility of being any one of many compounds that melt between 75 oC and
280 oC. How would you go about determining the melting point of the unknown (not the
identity)? (be sure to give specific ramp rates and start temperatures).
7) Predict the melting point of a mixture that is 90% acetylsalicylic acid and 10%
acetaminophen.

Recrystallization
3) What variables are you manipulating during recrystallization?
4) What is the equation to calculate % recovery? What does % recovery tell you – i.e. why
do people bother calculating it?
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Application:
5) Below are solubilites of compound A in a variety of different solvents at different
temperatures. Pick the best single solvent for recrystallization and explain your answer.

6) This one is a unit conversion question. Don’t let all the parts and numbers stress you out.
Given below is a table for solubility of compounds X & Y in solvent A. Answer the
following questions for 2.3 grams of impure compound X (contaminated by 11% Y by
weight).

Solubility per 100 mL of solvent A

Compound 0 oC 95 oC
X 0.17 g 6.3 g
Y 0.14 g 2.4 g

Show your work.

a. What is the mass of X in the 2.3 g mixture? What is the mass of Y in the 2.3 g
mixture?
b. What is the minimal volume of hot solvent A (at 95 oC) that is needed to
dissolve compound X (mass calculated in part a)?
c. How much compound X will recrystallize after cooled to 0 oC (assuming you
used the minimal amount of solvent)?
d. Will any compound Y crystals also form? If yes, how much?
e. Calculate the percent recovery of this process.
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7) How would each of the following choices affect the % recovery of a recrystallization?
Don’t just say it will change, how will it change? Explain your answer for each choice.

a. Placing the flask used for crystallization directly into an ice bath after removing
from the hot plate (assume the glass doesn't shatter)
b. Cooling the solution down below 0 oC (assume the solvent doesn't freeze)
c. Washing the crystals with room temperature solvent instead of cold solvent
d. Adding the solid into boiling hot solvent instead of adding the hot solvent drop-
wise to the solid

Distillation
3) What is the difference between simple and fractional distillation? When do you use each
one – be as specific as possible?
4) Name two ways to increase the number of theoretical plates in a distillation.
5) Explain how a fractional distillation produces a purer distillate than a simple distillation.

Applications:
6) Acetone has a boiling point of 56 oC and water has a boiling point of 100 oC. Which type
of distillation should you use to separate these two compounds?

Extraction
3) How do you determine which solvent is on top and which one is on the bottom?
4) How do you determine which compound is in each layer?
5) Describe how acid-base extraction works.

Applications:
6) Using the solubility chart below, decide which two solvents you would use for an
extraction to separate compound X and Y. Describe what the separatory funnel would
look like (which layer is on top/bottom, what compound is in each layer).

7) The painkiller Excedrin contains acetaminophen, aspirin, and caffeine.

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If no pKa value is provided, that molecule does not contain any acidic hydrogens.
Using the information provided above, describe what compounds are in each layer (and which
layer is on the top/bottom) of the separatory funnel for each of the following conditions.
EXPLAIN your answer.
a) Excedrin is dissolved in dichloromethane and 25% aqueous NaOH is added. Assume the
excedrin fully dissolves in the dichloromethane.
b) Excedrin is dissolved in ethyl acetate and 10% aqueous sodium bicarbonate is added.
Assume the Excedrin fully dissolves in the ethyl acetate.

TLC
3) How does solvent polarity affect Rf values?
4) How does compound polarity affect Rf values?
5) How is Rf value calculated?
6) What is the stationary phase and what is the mobile phase?
7) Name three errors that a chemist might do to get a wrong Rf value.
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Applications:
8) Answer the following questions for the TLC plate
shown to the right.

a. What is the Rf value for spot B?

b. Which compound is adsorbed strongest to the
stationary phase?
c. The TLC plate was developed using 25%
ethyl acetate (CH3CO2CH2CH3) and 75%
hexane. Sketch what the TLC plate would
look like if 50% ethyl acetate and 50%
hexane was used instead.

9) You run a TLC of a mixture of three compounds (shown below). Rank the compounds
from lowest Rf to highest Rf value. Explain your answer.

10) You want to determine which catalyst is the fastest for converting a ketone into an
alcohol. You run two different reactions (both starting with the same ketone and ending
with the same alcohol) with two different catalyst. You spot the two resulting reaction
mixture on the TLC: the one run with catalyst #1 on the left and the one run with catalyst
#2 on the right. According to the results from the TLC plate, which catalyst (#1 or #2) is
the fastest? Explain your answer.