Laboratory Report

Simulation 3.2 Elimination

Reaction

Presented by:
Agustin, Dean Adrian
Alinano, Jerome
Belza, Miko Aron
Bernal, Michael Justine
Crave, Kyle Angelo
Correa, Rhane

Submitted to:
Engr. Charles Bonn Kirby F. Mayo

October 18, 2022

I. Objectives

The objectives of this Simulation is to:

● Describe the E1 and E2 reactions' action modes.

● Compare how responsive various alkyl halides are to E1 and E2.
● Utilizing Zaitsev's rule, determine the outcome of an elimination.
● Make a prediction about the result of an E2 reaction's double-bond stereochemistry.

II. Introduction

Organic reactions called "elimination reactions" occur when one or two steps can be used
to remove two substituents from a molecule. E2 response is the two-step process, and the E1
reaction is known as the one-step mechanism. During this experiment cyclohexane, which is
produced by reacting cyclohexanol with phosphoric acid, has a utility. The elimination process
there has been an effort to find an alternative to phosphoric acid because there are limited
supplies of phosphor.

III. Materials and Procedure

● To access the Simulation, the materials needed are the following:

- LabPad - Ice bath
- Lab Coat/Lab Gown - Containers
- Safety Goggles - Condenser tube
- Gloves
- Round-bottom flask

● The procedure for this simulation are the following:

1. Learn how to access the LabPad then listen to the Simulator.
2. Wear a Lab Coat, Safety Goggles, and Gloves (to protect your body from the toxic
chemicals inside the laboratory).
3. If you are already in an appropriate and complete attire, you can now enter inside the
laboratory.
4. You are then assigned to help Kim (a research engineer at the polymer research lab) to
study polymers and to find out how the elimination of reactions works, why we are
seeing weird by-products when using HCl, and what a useful alternative could possibly
be.
 5. In the main lab room, brush over the concepts of organic chemistry over at the functional
groups poster and explore it. Kindly answer the provided questions in the lab pad with the
help of the functional group poster. Right after answering the questions, you can now
proceed to the experimentation needed.
6. To start with the experiment,
First, eliminate the bromide from the molecule and add the correct charges then place the
electron pair to the correct part of the molecule.
Second, place the containers on highest to lowest E1 reactivity.
Third, change the formation of the carbocation to make it stable
Fourth, change the molecules to lower the stability of the central carbon in a carbocation
intermediate.
7. By then, the alkyl halide will now enable the E2 elimination reaction on the molecule to
change it to double bond.

IV. Data and Results

This simulation teaches us about Elimination Reactions in Organic Chemistry. We

receive hands-on experience with alkyl halides and learn about their E1 and E2 eliminations.
Kim, a research scientist at a polymer research and manufacturing facility, was introduced to us.
They're having trouble optimizing their elimination process, which converts cyclohexanol to
cyclohexene, and they need our aid to figure out what's wrong and how to fix it. Back in the
main lab, we reviewed our organic chemistry knowledge. After we had a better grasp of Kim's
reaction, we looked at the two basic types of elimination reactions: E1 and E2. We were allowed
to manipulate molecules in order to understand the processes of the two reactions before being
challenged to find out Zaitsev's rule in an exploratory and interactive activity. We must also
determine which reactants are more likely to undergo the two reactions. We carefully study out
the processes of the two reactions and what controls their reactivity and the products they create
to solve Kim's production conundrum.

V. Discussion

Simulation; Elimination Reaction: Use cyclohexanol to create polymers is an online realistic

laboratory where students can learn reaction mechanism of E1 and E2, reactivity of different
alkyl halides towards E1 and E2, Zaitsev's rule, and the double bond stereochemistry in the
product in an E2 reaction.

• Elimination Reaction

In this mission, students are to find out how elimination reactions work, in the simulation
students are to learn about the functional group using the poster in order to learn a few key
concepts of organic chemistry, in the process leaving group is also discussed as well the
carbocation.

• Set up

In this mission, students are to learn about the different parts of the distillation set up and how
each part works. In the simulation the round bottom flask 250ml contains cyclohexanol and
phosphoric acid and if a reaction occurs the product of cyclohexanol will transfer to the round
bottom flask 100ml, where it has a lower boiling point than other compounds in the reaction
mixture.

• General version

In this mission, students are to learn about the general version of elimination reaction, often there
will be a base that extracts one of the side groups (substituents). The typical elimination reaction
within organic chemistry usually loses two substituents one each in the carbon atom and forms a
double bond between the two carbon atoms.

• Holo Table

In this mission, students are to carry out an E1 elimination reaction. First students are to identify
the leaving group, after identifying Alkyl halides which will be used in the elimination reaction
because halides are a good leaving group, students are now to eliminate bromine in the molecule
thus the main molecules are now carbocation. The next step is to extract the hydrogen atom to
eliminate the bromide and in this process the molecule will form a carbon-carbon double bond.

• Workbench 2

In this mission, students are to determine the least E1 reactivity molecule to the right and the
increasing E1 reactivity to the left, determine the order of reactivity toward the E1 reaction
pathway to know the stability of intermediate carbocation and the leaving group. In the E2
reaction it does not go to carbocation intermediate but happens only in one step, reactivity
towards the E2 reaction is the exact same for E1.

• Zaitsev's rule

In this mission, students are to learn about the Zaitsev's rule, the pattern for the main elimination
products is the more substituted double bond will yield the main product (more substituted
product = more stable).

• Holo Table 2

In this mission, students learn about the E2 type of elimination reaction. In the process the
special trait of E2 will be discussed which is the anti-periplanar, a product with trans
configuration will be far more dominant because the leaving group and the base-removed
hydrogen will tend to be antiperiplanar.
• Kim's problem

In this mission, students are to find alternative acids, specifically HCL, in the elimination
reaction that convert cyclohexanol to cyclohexene. The alternative to phosphoric acid is H2SO4.

The simulation is very informative as it provides information and guidance when handling
different missions, students learned about reactivity, Zaitsev's rule, alteration and reaction
product.

VI. Conclusion

In conclusion, we noticed that this simulation shows the reaction mechanism of the E2,
when a strong base is combined with an alkyl halide, elimination generally occurs by the E2
pathway, in which proton abstraction and loss of the leaving group occur simultaneously,
without an intervening carbocation intermediate but E1 eliminations can occur at secondary
carbons. However, if cyclohexanol is heated with a catalytic amount of phosphoric acid,
elimination of water results in cyclohexene as the product. Bothe E1 and E2 react differently. By
comparing the reactivity of E1 and E2, we can see that E1 is a first-order unimolecular reaction.
It is similar to a unimolecular nucleophilic substitution reaction in various ways. One being the
formation of a carbocation intermediate while E2 is a second-order bimolecular reaction,
meaning that both the substrate and the product have an impact on the rate of the reaction.

References
Signatures

Agustin, Dean Adrian

Alinano, Jerome

Belza, Miko Aron

Bernal, Michael Justine

 Crave, Kyle Angelo

Correa, Rhane

“I accept responsibility for my role in ensuring the integrity of the work submitted by the
group in which I participated.”