You are on page 1of 4

Synthesis of an Alkyl Halide Joseph G.

Catiis Institute of Chemistry, University of the Philippines, Diliman, Quezon City Date Performed: December 5, 2013 Date Submitted: January 7, 2014 Abstract The purpose of this experiment is to verify the usefulness of using a hydrogen halide to synthesize an alkyl halide from an alcohol using distillation. The alcohol and hydrogen halide are reacted inside a separatory funnel and are subsequently separated. The organic layer is treated with NaHCO3 and anhydrous CaCl2 to remove excess HCl and moisture, respectively. In the end, although a small % yield of 17.3570% was obtained because of an accident, an accurate boiling point of 50.7°C was obtained, verifying the usefulness of the experiment.

I. Introduction This experiment is aimed at synthesizing an alkyl halide (tert-butyl chloride) from an alcohol (tertbutyl alcohol) by reacting it with a hydrogen halide (hydrochloric acid). This happens via a unimolecular nucleophilic substitution reaction that will be discussed later. Also, as there is bound to be a side reaction, the experiment also includes purifying the product using simple distillation. The principle that governs the reaction that produces the alkyl halide is a kind of nucleophilic substitution reaction that is called an SN1 reaction. To summarize, the mechanism for the said reaction will lead to an overall reaction of

II. Methodology The experiment is divided into two parts: the synthesis part and the distillation part.

A. Synthesis Part First, 10 mL tert-butyl alcohol and 20 mL cold concentrated hydrochloric acid are measured. It is important to use an ice bath to assure that the HCl is cold. Next, the two reagents are transferred into a closed separatory funnel and swirled gently. Using an iron stand and an iron ring, the separatory funnel is allowed to settle undisturbed for 20 minutes so that the layers will separate. The stopcock of the separatory funnel should also be slightly open to facilitate the separation. Put a 50-mL Erlenmeyer flask below the set-up to be used later during the separation. For the separation of the layers to be facilitated, 3-5 mL of 6 M NaCl solution can be added into the mixture. Note however that adding too much will cause the formation of salt sands that might obstruct the mouth of the separatory funnel and prevent the separation. Determine which the organic layer is. The aqueous layer is where the NaCl solution goes, so the organic layer is the other layer. After determining this,

Figure 1: Overall unimolecular nucleophilic substitution reaction The purpose of this experiment is to verify if this reaction takes place by subsequently employing simple distillation to see if a distillate is obtained at the boiling point of tert-butyl chloride, and to what degree by solving for the percent yield.

The mixture is then swirled and decanted again. It is important that the flask be dry as this very flask will be used for the distillation. This was caused by an accident during the distillation Figure 4: Last Step in the nucleophilic substitution Lastly. Next. the following reactions took place Figure 2: First Step in the nucleophilic substitution First. causing the whole distillation process to terminate and leaving only a small amount of distillate. Immediately close the knob when the interphase between the two layers reaches the bottom of the funnel. spontaneous dissociation of the protonated alcohol occurs as a slow reaction. the result is caused by the mechanism of a unimolecular nucleophilic substitution reaction or an SN1 reaction. Stop distilling before the sample dries. Then.75 g Theoretical Amount: 9. Results and Discussion When the experiment was performed. B. Use a flask that is big enough such that the sample fills only 1/2 to 2/3 of its volume. the alcohol group is protonated by HCl.3570% process. . a small amount of anhydrous CaCl2 must be added to the mixture. Figure 3: Second Step in the nucleophilic substitution Then. the % yield is very small. the organic layer is to be transferred into a flask containing a small amount of solid NaHCO3. The joint connecting the flask to the rest of the distillation set-up was disconnected.separate the layers by slowly turning the knob of the separatory funnel and letting the liquid come out. Also make sure that the joints are fitted snuggly as accidental disassembly will prove to be a disastrous and unfortunate event. Table 1: Summary of Key Results As it can be seen. Record the boiling point and adjust the heat such that the flow rate of the distillate is 2 drops per second. the carbocation reacts with the chloride to produce the alkyl halide that is tert-butyl chloride.6791 g Actual Amount: 1. the following results are obtained tert-butyl alcohol tert-butyl chloride % Yield Initial amount: 7. According to the said mechanism.68 g 17. As stated earlier. This could have been avoided if the joints were checked properly. put a few boiling chips for the distillation. Distillation Part Assemble the distillation set-up accordingly: Make sure that water enters below and leaves above the condenser. III. Also. Assemble the flasks and turn on the water supply and slowly heat the sample. now into a dry 25-mL round bottom flask. it is then to be decanted into another flask. Once the mixture is swirled. Discard the first milliliter of distillate and continue collecting the distillate at constant temperature (49-52°C).

7°C) to the actual boiling point of tert-butyl chloride (51°C). Conclusion Given the data that are collected and the analyses at the discussions part. A continuous heat flow is necessary because if the water is not continuously replaced. the distillation process will not run as smoothly. diminishing the amount of distillate. chloride and carbonic acid. (2007) Organic Chemistry7th Edition. care must be observed. The experimenters had to improvise by using a stirring rod to get rid of the blockage. that happened in the separation using the separatory funnel. the bicarbonate will attack the hydrogen. Cengage Learning 2008 [2] McKenzie. Prentice Hall. VI. however. the procedures must be followed closely. salt sands formed and blocked the opening of the funnel.For this mechanism to work. If there is excess water in the mixture. ue to excessive addition of NaCl solution. However. New Jersey. it will add water to the mixture that is just separated from an aqueous layer. The point for improvement for the experiment is determining exactly how much NaCl solution is just enough to avoid the formation of salt sands. Anhydrous CaCl2 is added to the mixture to dry it because the mixture had to be as dry as possible. [3] Toss. given the closeness of the constant distilling temperature (50. the dissociation will produce an intermediate carbocation. New Jearsey. producing 2-methylpropene. there was also another accident. The proposed mechanism for the formation of 2methylpropene is an E1 elimination reaction or unimolecular elimination reaction. 1979. Aside from the distillation accident. References [1] Figure 5: First step of side reaction First. especially in distillation because a relatively structurally complicated set-up is involved. stressing the necessity to check for stability. IV. Experimental Organic Chemistry. already boiling so that they may adjust the heat source accordingly. J. the purity of the product cannot be assured because of the accident. That product is 2-methylpropene. D. Overall. solid NaHCO3 is used instead of an aqueous one because if an aqueous solution is used. 1967.7°C for this experiment. V. making it impossible to proceed with the separation. C. Boiling chips are added to give the experimenters a visual indication of when the sample is McMurry. If it were not for that. Figure 6: Second step of side reaction Then. Appendices . albeit less serious. Experimental Organic Chemistry. it can be assured because the first millilitre of distillate is discarded so that the distillate that is to be considered is the fraction that is garnered at constant temperature. the evaporated tert-butyl chloride will not condense. which is 50. we can say that using a hydrogen halide to synthesize an alkyl halide from an alcohol is an effective method. The significance of different steps in the procedures will be discussed. Prentice Hall. Cold HCl is used in the reaction because a certain side product is likely to predominate at warm conditions. In eliminating the excess HCl.