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OCHEM Lab 11

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4 views

OCHEM Lab 11

Uploaded by

lsutexan281
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Formation of a Bromohydril: An Addition Reaction

Lab Participants: Bailey Stewart, Rhett Herman, Sarwesh Karna


Lab Section: CHEM-3105-318
Lab TA: Brenda Alfaro
Date: 11/15/2024

Purpose
This lab aims to perform an electrophilic addition reaction by adding bromine and water to an
unsymmetrical alkene to produce a bromohydrin.

Reaction & Physical Properties

Safety: All Data Obtained from www.fishersci.com


● N-bromosuccinimide
○ Irritant and volatile
○ Handle with PPE at all times to avoid physical contact/exposure.
○ In the case of skin contact, remove contaminated clothing and rinse the skin with
water. If in the eyes, rinse the eyes with water for many minutes.
● 1-methylcyclohexane
○ Flammable and irritant
○ Keep away from flames and handle them with PPE at all times to avoid physical
contact/exposure.
○ In the case of skin contact, remove contaminated clothing and rinse the skin with
water. If in the eyes, rinse the eyes with water for many minutes.
● Tetrahydrofuran
○ Flammable and irritant
○ Keep away from flames and handle them with PPE at all times to avoid physical
contact/exposure.
○ In the case of skin contact, remove contaminated clothing and rinse the skin with
water. If in the eyes, rinse the eyes with water for many minutes.

Procedure
1. Add about 0.370 grams of NBS to a 5 mL conical vial with a spin vain. Add 1 mL of DI
water and 1 mL of THF. Next, add 240 microliters of 1-methylcyclohexane using a
micropipette set to 120 microliters.
2. Stir for 10 minutes.
3. Add 2 mL of DI water to the vial using a squirt bottle.
a. The level should be near the 5 mL line.
4. Stop stirring the mixture and allow the layers to separate.
a. The organic layer is on the bottom and the aqueous layer will be on the top.
5. Carefully pipet out the organic layer and add it to a shell vial.
a. If some water gets sucked up with the organic layer, allow the layers to separate
in the pipette and expel just the organic layer.
6. Dry the solution in the shell vial with anhydrous magnesium sulfate.
7. Create a silica gel column by pushing a small piece of cotton down a disposable pipe
and filling it half full with silica gel.
8. Pipette the dry organic layer into the silica gel column and add 1 mL of CH2Cl2 to the
vial with the remaining dry agent. Push the solution through the gel using a pipette bulb
into a clean and dry shell vial. Repeat the CH2Cl2 two more times so that the drying
agent is extracted.
a. Make sure to weigh the shell vial before adding any of the extract.
9. Evaporate the silica gel from the filtered solution by gently heating it on a hot plate set to
100℃-150℃ and blowing air onto it using compressed air through a tube.
a. Place the vial into a 50 mL beaker to avoid knocking it over during drying.
b. The product should be a clear liquid.
10. Weigh the product to calculate yield and obtain an IR spectrum from the product.

Data & Observations


● Shell vial weight: 4.1860g
● Shell vial with the product: 4.41261g
● Weight of product: 0.22661g
● The final product was not as orange as expected, although it was still the desired
substance. The reason behind the lack of color is unknown.
● The product took over ten minutes to evaporate and concentrate down to its final
volume.

Calculations & Results


● On the IR graph above, we can see the peaks one would expect to correspond with the
structure of the product, indicating that we experimented correctly. However, the peak
indicating the presence of an alcohol group is not as large as I would expect it to be,
although the TA stated that it was fine and we got a correct graph.
● Actual Amount of Product: 4.41261g - 4.1860g = 0.22661g
● Theoretical Amount:
○ 0.240 1-methylcyclohexene (MCH) = 0.000195g 1-methylcyclohexene.
○ 0.000195 x (1 mol 1-MCH/96.17g MCH) x (193.082g BMC/1 mol BMC)
= 0.000390782 x 1000 = 0.390782g
● Percentage yield: 0.22661g / 0.390782g = 57.99% Yield.

Conclusion/Discussion
I believe that this lab concerning the formation of a Bromohydril through an addition
reaction was successful. This reaction is important because it accurately demonstrates the
addition of additional substituents into the base structure of 1-methyl-cyclohexene by comparing
before and after IR graphs to show the addition of bonds to the substance.
This reaction is especially important because it demonstrates a common reaction found
in nature and by understanding how these reactions work, we can better apply these principles
to other labs as well as allow us to understand the lecture material we get in the connected
class.

Post Lab Questions


1. The product would be two enantiomers, with a bromide group on the left end attached by
a wedge and an alcohol group attached by a dashed line at the “peak” of the original
chain. The other enantiomer is the same structure but with the dash and wedge
switched, as is the custom of addition reactions.
2. The original compound had a double bond present between bromine and another
carbon, forming an alkene, but without this bond in the product, it would be absent from
the product’s IR graph.
3. A peak indicating an NH bond will be present in the graph, showing that the reaction is
not fully completed.

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