CHEM 2203 SP 2020

Lab Report Instructions for Expt 4C: Solvent Extraction II

General Information
• Your report MUST be typed and should NOT be submitted on laboratory notebook pages.
Much of the information and data from your lab notebook will be transferred to your report, but
you will not submit any lab notebook pages with or as part of your report. Copies of your lab
notebook pages should have been submitted when you left lab on the day of the experiment.
• The lab report is due at the beginning of the lab period on the week following the completion
of the experiment. For this experiment, the due dates are during the week of February 4.

Specific Information for the Solvent Extraction II Experiment

Your report will consist of the following sections. Use the headers listed below to designate each
section, except for the Title.

Title: The title of the experiment, the experiment number, and the date that the experiment was
performed in lab. This information is identical to that required in your pre-lab write-up. The title
should be complete and accurate:
Experiment 4C: Solvent Extraction II: Acid-Base Extraction Using A Two-Component Mixture
of an Acid and a Neutral Substance (or a Base and a Neutral Substance).
An incomplete title such as “Experiment 4C: Solvent Extraction II” is not sufficient.

Objective: List the goals, or the purpose, of the experiment. This information is identical to that
required in your pre-lab write-up.

Experimental Procedure: You do NOT need to copy the experimental details that were
included in your pre-lab write-up. It is sufficient to include a reference to the source of the
procedure, as well as any modifications that were posted on Canvas. If necessary, these
statements should be followed by a list of any additional modifications to the
experimental procedure (list in bulleted, complete sentences). It is very important that you
document any changes to the procedure in your lab notebook at the time of the experiment, and
include them in your report. This section may help to explain unexpected results, for instance.

Reaction Scheme: A balanced chemical reaction consistent with the experiment being
conducted, including reactants, products, solvent(s), and reaction temperature. This scheme is
identical to that required in your pre-lab write-up and should immediately precede the Data and
Results Table (see below). The reaction scheme may be hand-written, but please be as neat
and clear as possible.

Using any form of electronic copy and paste to reproduce directly a reaction scheme
from any source, including the printed or electronic lab textbook, is a violation of the
Academic Integrity policies of this course. All parts of your lab report – text, schemes,
tables, etc. – must be in your own words. You may draw the reaction scheme by hand
(preferred), or use some type of drawing program, but it must be your own work.
 Lab Report: Solvent Extraction II page 2

For this experiment, include a complete and balanced chemical equation for the
reaction that occurred in the separation step that you performed (just the separation
step – either 3 M HCl or 3 M NaOH, not the subsequent isolation step). Your answer should
consist of only one equation because you used a two-component mixture of the neutral
compound and the acid OR the base. The neutral compound should not appear in your
equation (why?).

Data and Results: Organized in three parts as shown below.

Data and Results Table
Give original data and calculated values in an organized tabular format, essentially, an updated
version of the Reaction Table from your pre-lab.
• Include appropriate units and pay attention to significant figures.
• Data may differ slightly from that reported in your pre-lab write-up. For example, you may
have weighed 73 mg of 9-fluorenone rather than the prescribed 75 mg. That is no problem at
all, but you must report and use the actual values in your calculations. In this way, your
final results and conclusions match what you actually did in the experiment, not what you
intended to do in your pre-lab.

As with the Reaction Scheme, using any form of electronic copy and paste to reproduce
directly a data table from any source, including the printed or electronic lab textbook, is
a violation of the Academic Integrity policies of this course. You are responsible for
creating your own table (either written by hand, or using Word or Excel).

Below is a sample Data and Results Table for this lab, and in this case, it may be used directly
in your report. This template is intended to help set expectations. Sample data covers the
scenario of a two-component mixture of 9-fluorenone (neutral) and ethyl 4-aminobenzoate
(base). Complete the appropriate compounds, amounts, and mmoles (mmoles not required for
the organic solvent diethyl ether) in the table with YOUR experimental data.

Ethyl 4- Diethyl HCl NaOH

9-Fluorenone
aminobenzoate ether 3M 6M
Mol. Formula C9H11NO2 C13H8O C4H10O HCl NaOH
Amount (mg)
Amount (mL)
mmoles
Concentration (M) 3.0 6.0
Molar Mass 165.19 180.20 74.12
Density (g/mL) 0.718
mp (°C) 89 84
bp (°C) 163-166 35

Observations
Data includes all relevant observations, such as heat evolved, initial color and color changes,
precipitate formation, state and color of product, product melting point range, etc.
Observations should be listed in bulleted, complete sentences.
 Lab Report: Solvent Extraction II page 3

Calculations
For all calculated values in Chem 2203, show ALL work. This part does not have to be
typed, and you may prefer to leave space in your document and enter the calculations by hand.
Please be as neat as possible.

Note the distinction between yield and % yield. A yield is simply an amount of product (how
much was formed?) and is also referred to as an actual or experimental yield. For example, the
yield of the reaction was 152 mg. A % yield relates how much of a product is produced (actual or
experimental yield) compared to the theoretical maximum that could have been formed
(theoretical yield). See pages 42-43 in the lab textbook.

Show ALL work! For this experiment, there is no overall chemical transformation of either
starting material, so the theoretical yields are simply the starting amounts.

Write or type all calculations, and be sure to include units:

1) Yield of 9-fluorenone recovered from diethyl ether layer
2) % Yield of 9-fluorenone
3) Yield of benzoic acid or ethyl 4-aminobenzoate recovered from aqueous layer (3 M NaOH or
3 M HCl)
4) % Yield of benzoic acid or ethyl 4-aminobenzoate

Questions: Answer the following questions. Be as complete as possible, and always explain
your reasoning.
1. Each of the solvents listed below are commonly used in experiments to extract organic
compounds from aqueous solutions. Will the organic phase be the upper (top) or lower
(bottom) layer when each of these solvents is mixed with water? Explain your answer in each
case, using appropriate supporting data.
a) Methylene chloride
b) Pentane
c) Diethyl ether
d) Toluene

2. Consider the chemical equation that you wrote for the Reaction Scheme. This chemical
transformation and its effect on compound solubility form the basis of this experiment and the
general technique of acid/base separations by solvent extraction. Hint: Recall the solvent
extraction I experiment (4B) from last week.
a) Comment on the relative solubilities of the organic reactant and product in the diethyl ether
phase vs the aqueous phase.
b) Explain why the solubility properties of the organic starting material change upon
conversion to the product. Please be specific in your explanation (hint: your explanation
should focus on polarity and intermolecular forces).

3. Write a complete and balanced chemical equation for the reaction that occurs during the
separation step that you DID NOT perform in Experiment 4C (just the separation step, using
either 3 M HCl or 3 M NaOH, not the subsequent isolation step). In other words, because you
began with a two-component mixture only, you skipped some of the procedure. What
happens in the first step that you omitted?
 Lab Report: Solvent Extraction II page 4

Works Cited: Full references for the experimental procedure(s) in the following format:
1. Mayo, D. W.; Pike, R. M.; Forbes, D. C. Microscale Organic Laboratory with Multistep and
Multiscale Syntheses, 5th ed.; John Wiley & Sons, Inc., 2011; pp 147-150.
2. Modifications for Expt 4C: Solvent Extraction II, Canvas document.