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Print Name: _________________________________________

1. Predict the products when the following compounds are treated with sodium hydroxide (base). (3 points)

2. Which is the more stable structure and why? (2 points)

3. Write the major product from the following reactions. (1+ 4= 5 points)


Write the mechanism for this reaction. (Hint: carbocationic rearrangement takes place)


  • Completion of Pre Lab Questions.
  • Write-up in your Lab Notebook.
  • Completion of Report Questions.
  • TA Points.

Materials required

Equipment Chemicals
Water bath with a beaker Anhydrous alcohol (Ethanol)
Reflux condenser Sodium metal
5 mL conical vial Needle
Stirring vane 2-bromobutane


Wear gloves all the time, especially when you use the metals. Keep safety glasses on all the time.

Experimental procedure

Preparation of the Alkoxide Base: Add to a 5.0 mL conical vial containing a magnetic spin vane 3-3.5 mL of the anhydrous alcohol (see Table 4.2). Add a 60-mg piece of potassium (or sodium) metal (or ~2 pellets) and immediately attach the vial to a reflux condenser closed by a lid. Place a needle above the reflux condenser to remove extra pressure generated during reflux. Place the whole arrangement in a water bath and, heat the mixture gently (~50°C) with stirring. (DO NOT HEAT THE CLOSED SYSTEM) When all the metal has reacted, remove the assembly from the water bath and cool to near room temperature (remove the needle).

Remove the lid from the condenser and use a calibrated Pasteur pipette to introduce 100 μ size 12{μ} {} L of 2-bromobutane down through the condenser into the vial. Place the assembly in the preheated water bath (see Table 1.3). Attach the gas delivery tube to the top of the condenser so that the open end of the tube is beneath the water level of the reservoir. If the connection to the top of the condenser is not made with an O-ring cap seal connection, lightly grease the ground-glass joint to insure a gas-tight seal. After about 10-15 minutes, air bubbles emerge. Place the water-filled gas collection tube over the open end of the gas delivery tube.

Isolation of Product: Collect about 6-7 mL of gas in the collection reservoir and then use a hypodermic syringe to withdraw a 0.7 to 0.8 mL sample through the rubber septum for GC analysis.

NOTE. Remove the gas delivery tube from the collecting reservoir and then from the water before discontinuing the heat on the reaction vial. This order of events prevents water from being drawn back into the reaction flask.

Purification and Characterization: The collected gas is analyzed by gas chromatography without further purification.


Handle sodium and potassium with care. These metals react vigorously with moisture and are kept under paraffin oil or xylene. Remove a small piece of metal from the oil using a pair of forceps or tongs-never use your fingers! Dry the metal quickly by pressing it with filter paper (to soak up the oil), and immediately add it to the alcohol in the reaction vial. Any residual pieces of sodium/potassium should be stored in a bottle marked“sodium/potassium residues." Never throw small pieces of these metals in the sink or in water.

Waste disposal

There will be a large beaker of isopropanol for you to dispense your unused metal. To destroy the metal, add small amounts to methanol.

Approximate lab time: 2.5-3 hours

Report: E2 Elimination (Total 30 Points)

On my honor, in preparing this report, I know that I am free to use references and consult with others. However, I cannot copy from other students’work or misrepresent my own data.

…………………………………………………………….. (signature)

Print Name: _________________________________________

1. Predict the more stable alkene and supply with reasons for your choice: (6 points)

(a) 1-hexene or trans-3-hexene

(b) trans-3-hexene or cis-3-hexene

(c) 2-methyl-2-hexene or 2,3-dimethyl-2-pentene

2. Starting with the appropriate alkyl halide and base-solvent combination, outline a synthesis that would yield each of the following alkenes as the major or only product and include your reasoning: (8 points)

(a) 1-Butene

(b) 3-Methyl-1-butene

(c) 2,3-Dimethyl-1-butene

(d) 4-Methylcyclohexene

3. When cis-1-bromo-4-tert-butylcyclohexane reacts with sodium ethoxide in ethanol, it reacts rapidly to yield 4-tert-butylcyclohexene. Under similar conditions, trans-1-bromo-4-tert-butylcyclohexane reacts very slowly. Using conformational chair structures, explain the difference in reactivity between these stereo isomers. (4 points)

4. Write the major product of the following reactions with proper stereochemistry.

(4+ 2+ 2+ 4= 12 points)

Questions & Answers

Is there any normative that regulates the use of silver nanoparticles?
Damian Reply
what king of growth are you checking .?
What fields keep nano created devices from performing or assimulating ? Magnetic fields ? Are do they assimilate ?
Stoney Reply
why we need to study biomolecules, molecular biology in nanotechnology?
Adin Reply
yes I'm doing my masters in nanotechnology, we are being studying all these domains as well..
what school?
biomolecules are e building blocks of every organics and inorganic materials.
anyone know any internet site where one can find nanotechnology papers?
Damian Reply
sciencedirect big data base
Introduction about quantum dots in nanotechnology
Praveena Reply
what does nano mean?
Anassong Reply
nano basically means 10^(-9). nanometer is a unit to measure length.
do you think it's worthwhile in the long term to study the effects and possibilities of nanotechnology on viral treatment?
Damian Reply
absolutely yes
how to know photocatalytic properties of tio2 nanoparticles...what to do now
Akash Reply
it is a goid question and i want to know the answer as well
characteristics of micro business
for teaching engĺish at school how nano technology help us
Do somebody tell me a best nano engineering book for beginners?
s. Reply
there is no specific books for beginners but there is book called principle of nanotechnology
what is fullerene does it is used to make bukky balls
Devang Reply
are you nano engineer ?
fullerene is a bucky ball aka Carbon 60 molecule. It was name by the architect Fuller. He design the geodesic dome. it resembles a soccer ball.
what is the actual application of fullerenes nowadays?
That is a great question Damian. best way to answer that question is to Google it. there are hundreds of applications for buck minister fullerenes, from medical to aerospace. you can also find plenty of research papers that will give you great detail on the potential applications of fullerenes.
what is the Synthesis, properties,and applications of carbon nano chemistry
Abhijith Reply
Mostly, they use nano carbon for electronics and for materials to be strengthened.
is Bucky paper clear?
carbon nanotubes has various application in fuel cells membrane, current research on cancer drug,and in electronics MEMS and NEMS etc
so some one know about replacing silicon atom with phosphorous in semiconductors device?
s. Reply
Yeah, it is a pain to say the least. You basically have to heat the substarte up to around 1000 degrees celcius then pass phosphene gas over top of it, which is explosive and toxic by the way, under very low pressure.
Do you know which machine is used to that process?
how to fabricate graphene ink ?
for screen printed electrodes ?
What is lattice structure?
s. Reply
of graphene you mean?
or in general
in general
Graphene has a hexagonal structure
On having this app for quite a bit time, Haven't realised there's a chat room in it.
what is biological synthesis of nanoparticles
Sanket Reply
how did you get the value of 2000N.What calculations are needed to arrive at it
Smarajit Reply
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Source:  OpenStax, Chem 215 spring08. OpenStax CNX. Mar 21, 2008 Download for free at http://cnx.org/content/col10496/1.8
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