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What can you say about the relative polarities of the starting materials and the products?

Abstract

This lab is used to show how to determine when a reaction has reached completion. It is also used to describe the polarity of the reaction and how to know when the reaction is polar, non-polar, or has intermediate polarity. This lab focuses on determining this using a TLC test, which is performed several times during the reaction. The TLC is also performed using organic material formed. This lab primary goal is to teach about polarity, TLC test, reaction completion, and to teach organic chemistry students some basic chemistry principles as applied in this lab.

Introduction

The purpose of this lab is to prepare a demonstration of the Alkene Hydration-3. I should be able to notice the outcomes of the change in structures on the reaction results.

Experimental Data

The starting materials were obtained from the stock room
Round Bottom Flask
1-MCHxene 1-methyl-cyclohexene
H2O (water)
The MCHxene and the methyl-cyclohexene were added to the flask
The flask was placed on the stir plate
Sulfuric acid (H2SO4) was added to the flask along with the other starting materials
A heating mantle was added under the flask to heat the mixture
A condenser was added to the flask so that the mixture can be refluxed
Nitrogen gas was added to maintain inert atmosphere and as well to prevent pressure build up during the reaction
The stir Plate was turned on and the reaction started
A TLC measurement was done at the begin of the reaction
A TLC test was done 15 minutes after the reaction had begun
Various TLC test were on at different time intervals as to record when the reaction came to completion.
The reaction mixture was added to a separatory funnel
H2O aqueous reagent was added to the funnel
Two thin layers of organic and aqueous phase were observed in the funnel
A TLC measurement was performed on the organic layer in the funnel 1-methyl-cyclohexanol
All lab materials were cleaned up and put away

Results

TLC Measurement – Stirred Mixture

11:31 (Start of Reaction) 11:36 11:20 11:35 (complete)

TLC Measument- Funnel Organic TLC –Stired Complete vs. Organic

Organic Stired Organic

Discussion

During the reaction

Questions

Why are the spots the same for both the right and left lanes at the start of the reaction?
This is because the reaction has only just begun and a complete reaction has not been yet completed. The reaction in fact has only just begun and we see no product being formed to consume the starting materials.

What is the new spot formed after 15 minutes?
The new spot is a result of products forming in the reaction.

What has happened to the size of the starting material spots? Why? (15 minute point)

How much time did it take to complete the reaction?
The reaction was started at 10:40am and was observed to be complete by the TLC measurement at 11:35am. This means the entire reaction took 1 hr 5minutes. There is however room for error because constant TLC test were on done, but instead done every 15 minutes or so.

What are the Rf value for the starting material and products?

What can you say about the relative polarities of the starting materials and the products?

Conclusions and Summary

References

Organic Chemistry, Seventh Edition, Paula Yurkanis Bruice

Virtual Chemistry Lab: Organic

Virtual ChemLab v2.5 Organic Synthesis and Organic Qualitative Analysis- Laboratory Workbook Student Manual

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