Procedure:
SN 1 Reaction
Procedure Observations Understanding
This reaction is conducted at room
Part 1. Reaction Set Up temperature with constant and
Construct RXN Apparatus: consistent stirring within a 25 mL
round-bottom flask.
1. Obtain a clean dry 25 mL round-bottom
flask (RBF) and stir bar to construct the ap- Starting Material & Reagents Draw the reaction scheme, including all reagents.
paratus.
Compound Quantity Physical
Properties
2. Mount the RBF with a clamp to the monkey
bars at a proper height so that the lab jack Diol (g)
and stir plate can be placed below. Ensure MW:146.23 (mol)
the lab jack can raise the stir plate to about (g/mol)
0.5” below the RBF. The RBF must NEVER 12N HCl (mL)
touch the top of the stir plate. MW: 36.46 (mol)
(g/mol)
Draw the reaction mechanism:
3. Weigh out 0.25 grams
of 2,5-dimethyl- 2,5- Reaction Product
hexanediol into a Compound Quantity Physical
weigh boat and add Properties
solid to flask inside the
Dihalide (mL)
hood.
MW: 183.12 (mol)
(g/mol)
4. Add 2 mL of con-
centrated (12 N)
hydrochloric acid to
the flask containing
the 2,5-dimethyl-2,5-
hexanediol. Stir.
Continued on next page
Laboratory Manual Prepared by Catalyst Education, LLC for Clemson University SN1.1
Department of Chemistry.
SN 1 Reaction
Continued from previous page
Procedure Observations Understanding
5. Record the reaction start time. RXN Start Time Which is the limiting reagent, HCl or Diol?
6. Watch reaction and make observations. Observations:
• Homogeneous or Heterogeneous/
Why?
• Color
• Physical State(s)
• Viscosity
7. Allow the reaction to run for 10 minutes. RXN End Time What does the resulting reaction look like?
Part 2. Reaction Quench, Work-Up, and
Isolation of Product
1. Add 10 mL of water to the reaction when
complete.
Continued on next page
Laboratory Manual Prepared by Catalyst Education, LLC for Clemson University SN1.2
Department of Chemistry.
SN 1 Reaction
Continued from previous page
Procedure Observations Understanding
2. Vacuum filter the contents of the reaction State the intermolecular forces present in
through a Bühner funnel. the starting material and product. Please draw
molecules to indicate IMF.
Who is George A. Olah?
3. Rinse the flask and the filtered solid with
copious amounts of water, and filter the re-
maining contents.
4. Wash the solid with a small amount of water.
5. Crush all material in the Büchner funnel to
increase surface area to accelerate drying. A
dry piece of filter paper can be used like a
sponge to soak the water from the substance
in the Büchner funnel. Allow the solid to dry
with vacuum suction for another 25-30 min-
utes.
Continued on next page
Laboratory Manual Prepared by Catalyst Education, LLC for Clemson University SN1.3
Department of Chemistry.
SN 1 Reaction
Continued from previous page
Procedure Observations Understanding
Part 3. Analysis
1. Find the mass of the product and calculate
percent yield Mass (g)
Discuss the melting point. Compare the melting
2. Obtain a melting point of the product. Melting Point Data point of the product to the reactant. Explain the
difference.
3. Obtain a TLC of the product. The UV light Onset
will not show these compounds but the PMA Meniscus
stain will. Clearpoint
Melting point range
Literature Melting Point
Reference
Continued on next page
Laboratory Manual Prepared by Catalyst Education, LLC for Clemson University SN1.4
Department of Chemistry.
SN 1 Reaction
Continued from previous page
Procedure Observations Understanding
4. Draw images of TLC and analyze the results TLC #2: PMA Has the reaction gone to completion? Use
to determine if the reaction went to comple- TLC to justify your answer.
tion
TLC (#1) shows UV visualization.
TLC (2) shows visualization with
a PMA stain.
Reaction time:
SM: 𝑅𝑓
Cospot: 𝑅𝑓 𝑅𝑓 𝑅𝑓
Rxn: 𝑅𝑓 𝑅𝑓 𝑅𝑓
Mobile Solvent System:
Continued on next page
Laboratory Manual Prepared by Catalyst Education, LLC for Clemson University SN1.5
Department of Chemistry.
SN 1 Reaction
Continued from previous page
Procedure Observations Understanding
5. Solubility of 2,5-dimethyl-2,5- Record the results of the solubility. Explain why some solvents better solvate/dis-
hexanediol solve the 2,5-dimethyl-2,5-hexanediol sample.
a. Obtain 3 clean test tubes and add 10-20
mg of 2,5-dimethyl-2,5-hexanediol. 2,5-dimethyl-2,5-hexanediol in methanol:
b. To the first test tube, add 0.50 mL of
methanol.
c. To the second test tube, add 0.50 mL of 2,5-dimethyl-2,5-hexanediol in hexanes:
hexanes.
d. To the third test tube, add 0.50 mL of
ethyl acetate. 2,5-dimethyl-2,5-hexanediol in ethyl acetate:
6. Solubility of 2,5-dichloro-2,5- Record the results of the solubility. Explain why some solvents better solvate/dis-
dimethylhexane: solve the 2,5-dichloro-2,5-dimethylhexane
sample.
a. Obtain 3 clean test tubes and 2,5-dichloro-2,5-dimethylhexane in methanol:
add 10-20 mg of 2,5-dichloro-2,5-
dimethylhexane.
b. To the first test tube, add 0.50 mL of 2,5-dichloro-2,5-dimethylhexane in hexanes:
methanol.
c. To the second test tube, add 0.50 mL of
hexanes. 2,5-dichloro-2,5-dimethylhexane in ethyl ac-
d. To the third test tube, add 0.50 mL of etate:
ethyl acetate.
Laboratory Manual Prepared by Catalyst Education, LLC for Clemson University SN1.6
Department of Chemistry.