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Chloronation of 1,1 Chlorobutane

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Submitted By ianmanderson
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1-Chlorobutane is an alkyl halide organic compound which is colorless and high combustible and rolithium reagent used as a strong base in organic synthesis and reacts aggressively with lithium to produce an organ known by the chemical formula of C4H9Cl. The percentage of the 4 different types of dichlorobutane were determined using gas chromatography including 1,1-dichlorobutane, 1,2-dichlorobutane, 1,3-dichlorobutane, and 1,4-dichlorobutane. By product distribution the relativity of each different type of hydrogen and its effect of the chloro-substituent was determined.
Experimental Method
1-chlorobutane, sulfurly chloride, and AIBN were moderately heated in a reflux apparatus. After the cooling another AIBN was added and the heat was turned back on to the same setting followed by cooling to room temperature. Following the cooling a separatory funnel was used to wash the organic solution with DI H2O, 5% sodium Bicarbonate, and then DI H2O again. Following the wasing the organic layer was dried with Anhydrous Sodium Sulfate to remove the excess H2O followed by the analysis using gas chromatography.
Gas chromatography was done on the radically chlorinated 1-chlorobutane to decipher which chlorination product, relative reactivity based on hydrogens of 1-chlorobutane, was the highest percentage between the four possible products, 1,1-dichlorobutane, 1,2-dichlorobutane, 1,3-dichlorobutane, and 1,4-dichlorobutane. As table 1 shows 1,3-dichlorobutane had the highest relative yield, 46.3%. 1,4-dichlorobutane was second with 24.6%, 1,2-dichlorobutane was third with 23.1%, and 1,1-dichlorobutane was the least relative yield at 6.0%, supporting the theory that chlorination on the same carbon with an existing chlorine would be caused by the electronegativity In all the ratios of the Hydrogens activity is 1.88 to 1.0 between the 1,3 Dicholorbutane and the 1,4 Dicholorobutane, the ratio between the 1,4 Dicholobutane and the 1,2 Dicholorbutane was 1.06 to 1.0 which was much closer than the larger different between the dominant and second highest data. Lastly was the 1,1 Dicholorbutane which was a mear 6% which in comparison to the 1,2 Dicholorbutane was a 3.85 to 1.0 ratio showing the truly drastic difference between the levels of activity due to Hydrogen placements. This difference showed that the reactivity of hydrogen with the same probability of substitution increases as the distance of the electrons increases from the center of the atoms.
The main reason for heating the solution was causing the AIBN to break the double bond between the two nitrogen’s holding the double bond together. This releases large amounts of nitrogen gas proportionate to the experiment. The breaking of this bond causes the reaction with the sulfuty chloride to creat chlorinated tertiary nitriles, followed by SO2Cl radicals which produces more sulfur dioxide. This process freed the Chlorine radicals to go after all four different positions of the Hydrogen atoms creating four different types of product all initiated as mentioned above by the use of heat and AIBN to split the nitrogen’s in the original compound.
Sulfur Chloride was used in this experiment due to it being a liquid which is easier to contain and control than it would be if a gas was used and makes it easier to measure out and AIBN due to it being known to spontaneously produce free radicals by the splitting of the nitrogen’s in the center of the AIBN molecule. The Hydrogens next to the intial Clourine were found to be least reactive, yet this proved that the 1,2 Sulfur Chloride was used in this experiment and the 1,3 Sulfur Chloride was used in this experiment had a secondary chlorination it seemed smoother and had a higher probability of occurrence. Throughout the process of studying the experiment it became obvious that the chlorination that occurred far from the original chlorine was the best. Through observations and in conclusion the reactivity of hydrogen with the same degree of substitution increases as the span on empty and occupied space from an initial halogen or electronegative atom increases.…...

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...allowing you adjust the box. To understand a little bit more behind the programming, we will revisit the code and modify it to be slightly more complex. In the Visual Basic Editor, we are going to modify the code to read “MsgBox Cells(1,1)” instead of “MsgBox (“Hello World”)”. Much like Microsoft Excel, VBA assumes that any text wrapped in “quotes” is plain text, whereas anything not wrapped in “quotes” is a function, procedure, or operation. Since there are no quotes around “Cells(1,1)”, it will not say “Hello Cells(1,1)”, instead, it will follow the command of Cells(1,1). The Cells(x,y) command is a function in Excel that instructs VBA to replace itself with the data from the spreadsheet row x, column y. Essentially the way VBA interprets this set of code is: MsgBox(“x”) “Create a message box with the text x” Replace (“x”) with Cells(1,1) Will now use the data from the cell located in row 1, column 1”. MsgBox Cells(1,1) “Create a message box with the data from row 1, column 1” Now go to the Cell A1 in the current Excel Sheet1 and type in “Bob”. Click on your Macro button, the result should be a message box that says “Hello Bob”. Hint: If you want to reference cells from other sheets, you can do this by typing Sheet3.Cells(1,1) This will now use the data from cell A1 on Sheet3 © Rotman School of Management Page 7 of 15 RIT API Tutorial We can make this more complex by adding an equation into the procedure. Go back......

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