You are on page 1of 2

Experiment 3: Preparation of 2-Chloro-2-methylbutane

Pre-Lab Homework Problems:

Chapter 4, pages 128-129: 1, 2, 5, 9
Chapter 4, page 133:
3, 5, 8
Chapter 14, pages 475-477: 1-3, 6-12
You will perform an SN1 reaction, followed by a series of extractions, and then finish
purifying your product by shortpath distillation, following the procedure on pages 473-474.
You will be using concentrated (12 M) hydrochloric acid. This is a very corrosive compound
and will cause permanent damage to skin and eyes. If you get any on your skin you must wash the
affected area with cold water immediately and remain under water while you have someone bring
you the bottle of saturated sodium bicarbonate in the reagent hood to rinse with as well. HCl in your
eyes must be rinsed out for 15 minutes. Any HCl spilled on the counters, hoods or floors must be
neutralized with the saturated bicarb solution until it no longer bubbles. All hoods and counters must
be wiped down before you leave lab. Do not leave without checking with your AI first.
Before you begin the reaction, put 10 mL of saturated sodium bicarbonate solution in a beaker
inside an ice bath. You will also be checking out a set of smaller glassware for the distillation from
the stockroom. You are responsible for cleaning all of your glassware and returning it to the
stockroom at the end of the lab or you will be charged for cleaning and replacement.
You will perform four different washes of your product in the separatory funnel. A wash is
an extraction that removes impurities. You will wash first with brine (a solution of saturated sodium
chloride), followed by saturated sodium bicarbonate which will remove any remaining HCl. When
washing with the saturated bicarb, follow the instructions in the procedure very carefully. The final
wash with brine is to help remove any remaining water from the previous extractions.
During the distillation you will collect everything that distills below 75 oC in a beaker. This
will be disposed of in the organic waste. Everything above 75 oC will be collected in a pre-weighed
vial or round-bottom flask sitting in an ice bath. This is your product, and it must be stored in your
drawer until the following week.
In the Analysis section of the procedure, you will not perform the silver nitrate or sodium
iodide tests. You will find the mass, calculate % yield, and collect an IR spectrum of your product.

Lab Report Instructions

At the end of lab, write a brief (1-2 sentence) Results section in your lab notebook,
summarizing what happened in lab and the mass of 2-chloro-2-methylbutane produced. Calculate
your % yield, showing how your equations are set up in the lab notebook.

After lab, you will write a discussion in your lab notebook. This is discussion will include
(not necessarily in this order, list may not be comprehensive):
Analysis of IR
Discussion of % yield. Come up with possible (and plausible) explanations for loss of
material/low % yields.
How successful was the experiment at providing pure product? What data do you have to
support your conclusion?
Any problems you encountered, errors committed, or anything you did that is different than
the procedure written in your lab notebook. Identify the cause of problems whenever possible.
Likely sources of error. Sources of error are not mistakes or accidents; they are limitations in
the procedure, technique or equipment that affect your results. Which were unavoidable? Are
there ways to improve the procedure to prevent some of these problems?
You will also write a Formal Experimental section which will be submitted to TurnItIn
through Canvas BEFORE the lab period when it is due.
The Formal Experimental should be double-spaced, 12 pt font. It will be graded based on
completeness, style, and format.
A Formal Experimental will always begin with a General Methods paragraph. Typically this
paragraph indicates the sources of chemicals used, whether they were purified further before use, and
the equipment and instruments used to perform the experiment, including model numbers for
Each reaction performed will be given a separate paragraph. The heading of the paragraph is
the name of the compound synthesized in bold. After the name, a detailed procedure will be given.
The procedure is written in past tense, passive voice. It will include the actual amounts of chemicals
used, in both grams (or mL) and moles, and will be written in enough detail that someone else could
repeat the procedure in exactly the same way. After the procedure the mass and % yield of the
product are given, as well as the appearance of the product (color and state of matter, other
descriptors if applicable). Finally, a summary of characteristic data such as melting point, Rf values,
major IR peaks, 13C- or 1H-NMR data, etc.
Here is an example of an experimental writeup for one compound reported in J. Org. Chem.
2011, 76, 9900-9918:
(3R,4R,E)-7-((E)-3-Iodoallylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl Acetate (30c). To a cooled
(0 C), stirred solution of vinylstannane 29c (543 mg, 1 mmol) in CH2Cl2 (33 mL) was added iodine
(381 mg, 1.5 mmol). After being stirred for 20 min at 0 C, the reaction was quenched with saturated
Na2S2O3 solution until the reaction mixture turned colorless. The organic layer was separated, and the
water layer was extracted with CH2Cl2 (2 20 mL). The combined organic layer was dried over
MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by column
chromatography on silica gel (15% EtOAc/hexane) to afford vinyl iodide 30c (367 mg, 97%) as a
slightly yellow thick oil: []20 D +8.9 (c = 3.6, CH2Cl2); 1H NMR (400 MHz, CDCl3) 6.65 (dd, J =
15.0, 8.0 Hz, 1H), 6.49 (dt, J = 14.5, 6.0 Hz, 1H), 6.24 (dt, J = 14.5, 1.5 Hz, 1H), 6.19 (br, 1H), 5.80
(dd, J = 15.5, 1.0 Hz, 1H), 4.70 (dd, J = 7.5, 5.0 Hz, 1H), 3.82 (m, 2 H), 2.56 (m, 1 H), 2.01 (s, 3H),
1.81 (m, 1 H), 0.98 (d, J = 7.0 Hz, 3H), 0.82 (d, J = 6.5 Hz, 3H), 0.81 (d, J = 7.0 Hz, 3H); 13C NMR
(75 MHz, CDCl3) 170.9, 165.5, 145.8, 141.4, 123.3, 79.7, 78.4, 43.5, 38.3, 29.7, 20.8, 19.6, 16.4,
15.1 ppm; IR (thin film) max 3280, 2967, 1739, 1669, 1632, 1240, 1020 cm1; HRMS (CI/NH3) m/z
calcd for C14H23INO3 [M + H]+ 380.0723, found 380.0718.