Experimental Plan for Lab Group Project

Name _____Liz Subrin______________________ Group Number 6______ Section __6745____________

Each member of your research group must fill out an Experimental Plan sheet pertaining only to the reaction they
are assigned. Each researcher must perform one of the three reactions. You should also retain a copy of this plan
to help guide you through your experiment. You may want to meet briefly before submitting your Experimental
Plans to the TA to ensure the group is on the same page. Submit a computer-created paper copy of this
Experimental Plan, no hand-writing on this Exp. Plan!

Reaction (draw the reaction scheme including starting material, reagents and expected product):






Fill in the reagent table below as completely as possible:
Chemical Name Mass or Volume Required Moles Needed Misc. Chemical Properties
Sulfuric Acid (H2SO4) 5 mL 0.045 mol 9M
98.08 g/mol
270C BP
-35C MP
1.84 g/mL
Miscible in H2O
Sodium Bromide (NaBr) 2.88g 0.028 mol 102.91 g/mol
3.21 g/mL
1 g/ 1.1 mL H2O
Sodium Bicarbonate 1.05 g (in 20 mL of H2O) 0.012 mol

Detailed Procedure: (list all important steps of the reaction, separation, purification, and analysis; be very
practical and detailed)

The type of reaction performed is hypothesized to be a bimolecular nucleophilic substitution (SN2). Since
3-phenyl-1-proponal is an alcohol, it can be dehydrated with an acid heated up, which is an elimination acid/base
reaction. The alcoholic oxygen is nucleophilic and attacks the electrophilic carbon in order to displace the water
molecule. This protonation is done in order to form a good leaving group and allow a substitution. The substitution
involves the nucleophilic bromide in the sodium bromide attacking the electrophilic carbocation in order to create
the alkyl bromide.

Reaction
Mix 3.5 grams of 3-phenyl-1-proponal with about 2.8 grams of sodium bromide. Then carefully add 5
milliliters of sulfuric acid and a few boiling chips. Using a thermowell, slowly heat up the solution in a round
bottom flask to a gentle boil after turning on the condenser. Heat for about 30 minutes and the let cool to room
temperature. Due to breaking the bond and forming a water molecule, part of the reaction is endothermic.
Separation
After cooling, two layers should form: an aqueous layer with sulfuric acid and hydrogen bromide, and the
organic layer with 1-bromo-3-phenylpropane and possibly some 3-phenyl-1-proponal. Transfer liquid to a
separatory funnel without boiling chips. About 15 milliliters of water can be added to better distinguish the two
layers since both organic compounds are insoluble in water. Be sure to properly vent and gently shake during this
washing process. Drain organic layer from separatory funnel and then perform the following step twice, to ensure
minimal amount of impurities. Discard the aqueous layer and utilize only the organic layer collected. Add 10
milliliters of 5% concentrated sodium bicarbonate and drain the organic layer. This neutralizes the acids that were
left in the organic layer. Dry the organic layer with sodium sulfate to ensure there is no water in this product. Then
use gravity filtration to collect purified product.
Analyze
Using the GOW-Mac Model 69-400-TCD GC, analyze 2.5 microliters of the end product, making sure all
possible peaks have eluted. Be sure to add dichloromethane as a 1:1 ratio to ensure there is no water in the product.
Use the Thermo-Nicolet 380 FT-IR to analyze the liquid organic compound and make a table if necessary to
represent important peaks. Once best result from the experiments is found, weigh about 17 milligrams of product
and add 15 milliliters of CDCl3 to use the Varian Gemini 200 MHz NMR to show the related peaks of hydrogens.


Schedule (briefly explain each days activities toward solving the problem and preparing your article):
Day 1: Completed reaction and separation procedure. Need to dry and analyze GC and IR.
Day 2: Realized error in measurements. Immediately restarted reaction and separation procedure.
Day 3: Dried product from second experiment and analyzed GC and IR, while performing third reaction and
separation procedure. Added time to reflux and increased concentration of sodium bicarbonate. Dried product.
Day 4: Analyzed GC and IR. Determined product 3 had best results, used 1HNMR to prove theory.

Results
Experiment 2 Experiment 3
Starting material 3.509 g 3.82 g
Sulfuric Acid 5 mL 8 mL
Sodium Bromide 2.97 g 4.057 g
Reflux Time 25 minutes 55 minutes
Temperature at Separation 15C 6C
Amount of water 15 mL 15mL
Concentration of Sodium
Bicarbonate
5% of 20 mL 10% of 20mL
Product ~17 mg ~45 mg

In both experiments, contrary to hypothetical JOC note, the step of putting the product recovered from the reflux in
an ice bath was added. The solubility of some of the reagents increases if the temperature is lower between around
15-0 C.

Experiment 3
* Increased amount of starting material
* Increased amount of sodium bromide (used more than starting material)
* Increased amount of sulfuric acid
* Increased time of reflux by 30 minutes
* Increased concentration of sodium bicarbonate by 5%