CHEM 340L ETSU Studying SN1 & SN2 Reactions Nucleophilic Substitution Report

Dr. Irina SmoliakovaChem 340L, Survey of Organic Chemistry Lab
Experiment 6
Studying SN1 and SN2 Reactions: Nucleophilic Substitution at Saturated
Carbon
The following are the major steps of Experiment 6:
(i)
(ii)
(iii)
(iv)
(v)
Read and understand the experiment description in the lab manual.
Read the PP slides prepared by the course instructor.
Watch three YouTube videos by clicking on the following links:


https://www.youtube.com/watch?v=yaL3iNVIgzM (you can skip the measurement of
refractive index at the end of the third video)
Write Report 6 (see the guidelines below) and upload your report in Blackboard
by the deadline.
Take Lab Quiz 6 on Bb.
If you have questions, contact Dr. Smoliakova or your TA.
Guidelines for Prelab Quiz 6 (a total of 10 pts)
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
Know names, structures and properties (p. 92) of all organic and inorganic
compounds used in the experiment. You do not need to memorize the numbers
given in the Table on p. 92; however, you need to know the physical state—a
liquid, gas or solid—of each chemical used in the experiment.
Density of the major organic product relative to that of water.
Immiscibility of 1-bromobutane in water. Limited solubility of 1-butanol in water.
Know the techniques (e.g., distillation and extraction), equipment and
glassware, which will be used in the experiment.
Major steps of the procedure described in the lab manual.
The reaction equation for the synthesis of 1-bromobutane from 1-butanol and
hydrobromic acid.
Identify the role of each chemical in the experiment: a reagent, product, solvent,
catalyst, drying agent, or base.
What is the mechanism of the reaction, SN1 or SN2? Why? What is the leaving
group in the reaction?
What other methods do you know for the preparation of alkyl halides?
What does “anhydrous” mean? What is the role of anhydrous CaCl2? What other
salts can be used for the same purpose?
Safety issues during the experiment.
Report 6 (a total of 30 pts)
1. Prelab Section (10 pts)
a. (1 pt) Write your name, class #, lab section #, the number and title of the
experiment.
b. (1 pt) Write the purpose(s) of the experiment.
* This document was prepared by Dr. Smoliakova and used with her permission
Dr. Irina Smoliakova
Chem 340L, Survey of Organic Chemistry Lab
c. (8 pts) Draw and complete the following table. Use the amounts of all reactants
indicated in the lab manual.
Name of the
Compound
Structure of Physical State Molecular
the
and
Weight
Compound
Appearance
1-butanol
(a reactant)
hydrobromic
acid
(a reactant)
1-bromobutane
(a product)
sulfuric acid
(a catalyst)
Amount Used in Amount Used Hazards
g (for solids) or in Moles
mL (for liquids)
calculate and
write the
theoretical yield
of the product in
grams
n/a
calculate
and
write
the
theoretical yield
of the product in
moles
n/a
2.
Observation Section of the report (10 pts)
Describe all steps of the experiment shown in three recommended videos. (You
can skip the measurement of refractive index at the end of the third video.) In
this section, please use the numbers shown in the video.
3.
Results/Conclusion Section of your report (a total of 10 pts)
a. (4 pts) Answer question 1 on page 99, “Calculate the percent yield of 1bromobutane obtained in your experiment.” In your calculations, please use the
amounts of reactants given in the lab manual. ASSUME THAT 3.5 mL OF PURE
1-BROMOBUTANE WAS ISOLATED IN THE EXPERIMENT. Take into account the
following information: you used concentrated hydrobromic acid, which is a 48%
solution of HBr in water. You need to use the following information in your
calculations: one liter of the hydrobromic acid used in the experiment contains
8.8 moles of pure HBr. Show your calculations in the report.
b. (1 pt) What does “anhydrous” mean?
c. (1 pt) Answer question 5 on page 101, “What is the function of anhydrous CaCl2
in this experiment?”
d. (a total of 4 pts) Decide if this reaction proceeds through the SN1 or SN2
mechanism (0.5 pt). Explain your answer (1 pt). Propose and write the detailed
mechanism of the reaction (2 pts; you must show arrows). What is the leaving
group in this reaction (0.5 pt)?

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