Organic Lab 7

Amanda Jornd Experiment 7- Synthesis and Reactivity of tert-Butyl Chloride Via an SN1 Reaction launch/Background Alkyl halides are compounds in which a halogen atom replaces a hydrogen atom of an alkane. Alkyl halides are classified as primary, unoriginal or ordinal depending on the number of alkyl substituents directly attached to the carbon attached to the halogen atom. The purpose of this lab was to flop prepare t-butyl chloride from t-butyl-alcohol in a knockout hydrochloric acid.The reception occurs finished a nucleophilic substitution, which is when a nucleophile replaces the deviation company in the substrate. In this lab, the hydroxyl group of t-butyl alcohol is re position by a chlorine atom. The fightion proceeds with an SN1 mechanism (Weldegirma 38-41). A nucleophile is any neutral or uncharged molecule with an unshared check of electrons. In the substitution answer, the nucleophile donates an electron pair to the substrate, leading to the formation of a new bond to the nucleophile, while breaking the existing bond to the go forth group (Solomons and Fryhle 99-102).The devil types of nucleophilic substitution receptions, SN1 and SN2, are identified based on whether the different steps occur simultaneously (SN1) or in two separate steps (SN2). To synthesize the t-butyl chloride, the t-butyl alcohol goes through an SN1 reaction. Also, the nature of the termination can affect which substitution reaction will occur. Polar protic roots typically promote SN1 reactions. This is because the SN1 mechanism is carried out in two steps and the arctic protic solvent produces both a cation and an anion which are capable of stabilizing the charges on the ions form during the reaction.Because an SN2 reaction occurs in one step, this is unfavorable however, the SN2 reactions tend to favor polar aprotic solvents. A nonher factor affecting the type of substitution reaction is the nature of the expi dimensionn group. Since the SN1 reactions occur i n one step, they generally film an excellent leaving group and wont typically abide with a poor leaving group. The SN2 reaction also favors excellent leaving groups but can run with any type of leaving group because it is run in two different steps. To synthesize the t-butyl chloride, the t-butyl alcohol goes through an SN1 reaction. Weldegirma 38-41). Mechanism of the preparation of tert-butyl chloride Possible side reaction during the preparation of tert-butyl chloride experimental Section/Flow Chart Part 1 60mL separatory funnel + cooled 15mL of concentrated HCl to 0? C + added 15mL of HCl to separatory funnel + added 5mL tert-butyl alcohol +swirled it without the stopper for 20 proceedings + let last until two distinct points were organize + drained cut layer into Erlenmeyer flask and saved estimable incase Organic Layer- in separatory funnel +added 30mL of DI water + swirled for a few proceedings let stand until two distinct layers formed + drew off lower layer into E rlenmeyer flask and saved near incase Organic Layer- in separatory funnel shape + added 15mL of 5% sodium bicarbonate + shook with stopper with venting + let stand for a few minutes until two distinct layers formed + drew off lower layer into Erlenmeyer flask and kept just incase Organic Layer- in separatory funnel + added 15mL of water + swirled for a twain minutes + let stand until two distinct layers have formed + drew off lower layer into Erlenmeyer flask and kept just incase Organic Layer transferred proceeds layer into clean/ change out 125 mL Erlenmeyer flask + added 1. 5 grams of anhydrous atomic number 20 chloride to dry the product +decanted into round bottom flask + added 6 boiling stones + ran through a simple distillation Tert-Butyl Chloride Part 2- try on render 1- + added . 1mL tert-butyl chloride from set off 1 + added 1mL of NaI + shook while holding top of exam supply with feel + recorded time, look, color, etc. interdict Result sort furnish 2- + adde d . 1mL tert-butyl chloride from part 1 + added 1mL of AgNO3 + shook while holding top of test tube with finger recorded time, look, color, etc. Positive Result Test tubing 3- + added . 2mL tert-chloro butane + added 1mL of NaI + shook while holding top of test tube with finger + recorded time, look, color, etc. Positive Result Test pipage 4- + added . 2mL tert-chloro butane + added 1mL of AgNO3 + shook while holding top of test tube with finger + recorded time, look, color, etc. Negative Result mesa of Chemicals Table of Chemicals 1 Table of Chemicals 1 Chemical Name- Physical Properties- Chemical Properties- Tert-Butyl Alcohol- M. P. -25-26 ? CB. P. 82-83? CMolecular Weight- 74. 2 g/molWater Solubility- miscible Combustible- noFlammable- yes Hydrochloric Acid- M. P. -114? CB. P. -85. 05? CMolecular Weight-36. 4 g/mol Combustible- yesFlammable- no Sodium bicarbonate-(Chembook) (Chembook) M. P. 50? CB. P. 851? CMolecular Weight- 84 g/molWater Solubility- 9 g/ coulombmL C ombustible- noFlammable-no Table of Chemicals 2 Table of Chemicals 2 Tert-butyl chloride- M. P. -26? CB. P. 51? CMolecular Weight- 92. 57 g/molWater Solubility- sparingly Combustible- noFlammable-yes Anhydrous calcium chloride- M. P. 772? CB. P. 1935?CMolecular Weight- 110. 98 g/molWater Solubility- 74. 5 g/ 100mL Combustible- yes/ slightlyFlammable- no Silver nitrate- M. P. 212? CB. P. 444? CMolecular Weight- 169. 87 g/molWater Solubility- 122 g/100mL Combustible- noFlammable- no Sodium iodide-(Chembook) (Chembook) M. P. 661? CB. P. 1304? CMolecular Weight- 149. 89 g/molWater Solubility- 178. 8 g / 100mL Combustible- noFlammable- no Table of Chemicals 3 Table of Chemicals 3 1-chlorobutane- (Chembook) (Chembook) M. P. -123? CB. P. 78? CMolecular Weight- 92. 57 g/molWater Solubility- . g/L Combustible- YesFlammable-Yes Results Percent Yield- t-butyl alcohol closeness = battalion/Volume M= . 842 x 5 = 4. 21 grams Mass/ M. W. = moles 4. 21 g / 74. 12 g/mol = . 0568 mo les of t-butyl alcohol t-butyl chloride tautness = Mass / Volume M= . 397 x 2 = . 794 grams mass / M. W. = moles . 794 g / 92. 57 g/mol = . 00858 moles of t-butyl chloride Because of a 11 ratio then you can use actual / theoretical x 100 . 00858 moles / . 0568 moles x 100 = 15. 105 % Results Table 1 Results Table 1 Color Precipitate appearance Time of precipitant After change water (50?C) bath Positive or Negative Result Test Tube 1- T-butyl chloride & NaI Clear/ faint tint of yellow No hasty Over 6 minutes and still no precipitate cypher occurred after 6 minutes in the steam bath Negative Result Test Tube 2- T-butyl chloride & AgNO3 Cloudy and ashen Yes, small substantial particles . 8 seconds N/A Positive Result Test Tube 3- t-chloro butane & NaI Slightly cloudy with initial drop but quickly sullen clear No precipitate after 6 minutes 6 minutes RT, for steam bath 4 minutes 58 seconds chicken solution as well as white precipitate on bottom formed. Positive Result Te st Tube 4- t-chloro butane & AgNO3 Clear dull liquid No precipitate 6 minutes RT, 6 minutes steam bath No precipitate Negative Result backchat Throughout this lab, the main goal was to properly throw a t-butyl chloride. In order to test if we properly received our product we tested the standard with two different solvents, a solvent of sodium iodide and argent nitrate. If an alkyl halide is a tertiary one, it can easily react with a solvent of silver grey nitrate to generate a relatively stable tertiary carbocation through an SN1 reaction.If an alkyl halide is a primary one, it can then react with iodide ions in the sodium iodide solvent by an SN2 mechanism showing a precipitate of insoluble sodium chloride. Heat can also be used in this process to speed up the reaction (Weldegirma 38-41). The number one test we ran was t-butyl chloride and sodium iodine. After mixing the two compounds, on that point was exactly a slight tint to the liquid but remained clear and precipitate free for 6 minutes of being populate temperature. We then placed it in a warm water in which there was no precipitate that formed while being heated.This test yielded a disallow result. The second test that we ran was t-butyl chloride and silver nitrate. Directly after mixing the compounds, there was an immediate white precipitate that had formed. This test yielded a positive result. A electronegative result with sodium iodide and a positive result of silver nitrate concluded that our solution of t-butyl chloride was a pure tertiary alkyl halide. Our third test was run with t-chloro butane and sodium iodide. This test initially did not form a precipitate while it was kept at room temperature.We then used a warm water bath in which after 5 minutes the solution formed a white precipitate and a yellow liquid. This shows that this test was a positive test. The one-quarter test was with t-chloro butane and silver nitrate. This test did not form a precipitate at room temperature or d uring the steam bath. This shows a negative result. With the t-chloro butane, the negative result with silver nitrate and the positive result of sodium iodide fire that this is indeed a primary alkyl halide. ConclusionIn this lab, we properly carried out an SN1 reaction from t-butyl alcohol to t-butyl chloride and found that we did in fact create a t-butyl chloride by getting a positive result from our silver nitrate test in the end. Although we werent able to visibly rule with our eye the nucleophilic attack, the steps that we carried out in the lab showed the separated layers and that there were reactions going on during each step. The organic layer that was continuously swear out was undergoing the slow reaction process during each separating stage.In the end, after the distillation of the solution, the SN1 reaction was completely carried out. The information from this data has revealed that it is possible to run for out an SN1 reaction in a lab however, in the process of was hing the product there will be a lot of material befogged giving a low percent yield in the end. It would be smart to use chemicals that are inexpensive and in large quantities to carry out these types of reactions. The information and techniques performed in this lab could be applied to otherwise situations in an industrial setting.One example of this could be creating chlorofluorocarbons which used to be produced for aerosol container cans and other products. Although these are no longer widely used in the world due to ozone effect, the SN1 reaction could be done with these chemicals. Overall, the lab gracious what it was set out to do. References Chemical Book. 2008.