Lab 4 - Beyond Labz - Hydrohalogenation and Bromination PDF

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This is a lab for Organic Chemistry I for the Summer 2021 semester from Charles R. Drew University of Medicine and Science....

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Princelawrenz C. Hamlin Lab Partner: None Lab Performed: June 17, 2021

Organic Chemistry I Charles Drew University Summer 2021

Lab-4: Beyond Labz - Hydrohalogenation and Bromination

Introduction: In this experiment, we will be determining whether or not our product is pure through hydrohalogenation and bromination. We know that halogenation is an electrophilic addition reaction in which a diatomic halogen molecule reacts with the pi bonds of a compound. A hydrohalogen such as H-Cl (which we will be using in this experiment) reacts with the Pi bonds in a Markovnikov formation where the halogen binds with the most substituted carbon. tertiary>secondary>primary. We will perform a halogenation reaction to analyze and properly decipher our answer.

Materials:         

Ethanol Personal Protective Equipment Buchner Funnel Methanol Filter Paper Hot Plate Trans-Stilbene Filter Paper Magnetic Stirrer (and Stir Bar)

Procedure: 1. First, we add 10ml worth of ethanol in the 25ml Erlenmeyer flask and magnetic stirring bar; and proceed with including 250 mg of trans-stilbene to the flask. 2. At this point, we activate the magnetic stirrer and the heating plate so that we can boil off the trans-stilbene. 3. We then proceed to include 500mg of Pyridium Tribromide. 4. After about 10 minutes, we then remove the flask from the heating plate and establish the Buchner funnel to collect the white solid. 5. Finally, we rinse the flask with methanol and wait for the remaining solvent to evaporate out of the flask. Results: Upon adding the diethyl-ether, we discovered that it ended up in the aqueous layer. We proceeded to use the 1-Methyl-cyclohexane; whereby the hydrogen binds to the more substituted tertiary carbon with respect to the methyl group. We used HCL for our reagent and incorporated 1

Princelawrenz C. Hamlin Lab Partner: None Lab Performed: June 17, 2021

Organic Chemistry I Charles Drew University Summer 2021

TCL to determine how much our values changed. After about an hour, our final product was 1Chloro-methyl-cyclohexane and thus a Markovnikov.

Conclusion: This lab taught us new ways to approach hydrohalogenation and bromination reactions and refined our understanding of the Markovnikov principle. Personally, I would say one of the most integral aspects of this lab was learning how hydrogen naturally binds to the more substituted carbon in any circumstance. Finally, using HCL as the reagent helped us to determine that our final product was 1-Chloro-methyl-cyclohexane (AKA, a Markovnikov).

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