Abstraction: Alkyl halides can be synthesized from intoxicants through its reaction with strong acids moving as H halides. HX ( X = Cl. Br. I ) . The mechanisms of acid-catalyzed permutation of intoxicants can be classified as either SN1 or SN2. where SN stands for nucleophilic subsitution and 1 or 2 denominating its molecularity. The chief aim of the experiment was to synthesise tert-butyl chloride with the use of an SN1 mechanism and sublimating it with a simple distillment set-up. wherein a mixture of different substances separate by taking advantage of the different volatility and boiling points of the single constituents. Third intoxicants are the most contributing intoxicants whenever those must be synthesized into alkyl halides. In the experiment. hydrochloric acid was used in order to respond with tert-butyl chloride to bring forth tert-butyl intoxicant through an SN1 reaction. This reation includes three stairss. The first portion is the rapid. reversible ( through hydrolysis ) protonation of the intoxicant followed by a slower rate-determining measure which is the loss of H2O. finally bring forthing a more stable third carbocation.

To reason the procedure. the carbocation is fleetly attack by the halogen ion ( chloride in this experiment ) in order to organize the alkyl halide. Alkyl halide is indissoluble in H2O. doing it easy for it to divide from the aqueous bed. Hydrochloric acid was so assorted with tert-butyl intoxicant bring forthing H2O and tert-butyl chloride and was purified through distillment. Finally. a clear and colourless solution of alkyl halide was synthesized. 0. 8 millilitres in volume. with merely a 7. 38 % percent output. It can be concluded that the synthesis of alkyl halides with the reaction between an intoxicant and a strong acid is an accurate and effectual purification process.


Alkyl halides are compounds which have the general expression R – X. where R is normally an alkyl group with a halogen. such as Cl or Br. replacements in topographic point of one of the Hs. It can besides be referred to as alkyl halides or halogenoalkanes. Multiple permutations of halogens for Hs can take topographic point. and in the procedure. may bring forth certain fluctuations wherein non merely methane seriess are involved but olefines and acetylenes every bit good. The presence of the extremely negatively charged halogen in alkyl halides tend to lend to its increased mutual opposition. Alkyl halides can be classified depending on the figure of alkyl substituents attached to the carbocation. It can be primary. secondary or third. Soon. the applications of the construct of alkyl halides can still be seen.

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This includes the usage of C tetrachloride for fire asphyxiators and fabric cleaners and CFCs ( CFCs ) which are normally a portion in the procedure of doing air conditioners. Because of the prevailing industrial and commercial benefits which arise from the usage of alkyl halides. it is important that techniques must be developed in order to be able to fix. isolate and get alkyl halides in the purest possible signifier. Two procedures can be used in order to fix or synthesise alkyl halides. One of the two methods which are used is the reaction of intoxicants with S and phosphoric halides. During the reaction between intoxicants and S or phosphoric halides such as thionyl chloride ( SOCl2- ) . phosphoric trichloride ( PCl3- ) . phosphoric pentachloride ( PCl5- ) or phosphoric tribromide ( PBr3 ) . in the procedure. alkyl halides can be derived from intoxicants. An illustration of that is the synthesis of ethyl chloride or ethyl bromide from the reaction of ethyl intoxicant with either S or phosphoric halides. However. the more commonly used among the two is the one which involves the reaction of intoxicants with the halide ions in strongly acidic environments in order to synthesise alkyl halides.

Distillation is one the commonly used methods for the purification of liquids and dividing a mixture of different liquids into its single constituents. It is intended for the more volatile liquid to vaporize in a solution of less volatile and/or non-volatile substances. The vapour is so cooled. hence. condenses in that procedure which consequences in the liquid collected with the receiving system in the distillment set-up. This may be executed due to the different boiling points of the single constituents of the mixture. One utile illustration of distillment includes the fractional process of rough oil into more good and utile merchandises such as gasolene and warming oil.

The intent of the experiment is to be able to understand as to how intoxicant and alkyl halides are connected to each other with regard to the mechanisms of the reactions. The synthesis of an alkyl halide from alcohols requires the public-service corporation of third intoxicants which contribute to the comparative strength and stableness of the third carbocations. Since secondary and primary carbocations are comparative weak and unstable compared to third carbocations. this normally consequences in the derivation of unequal alkyl halides. In add-on to that. the usage of more complex intoxicant does non ensue in the merchandise of more satisfactory alkyl halides. The ground behind it is that more complex intoxicants tend to respond more with strong acids which can impact the measure of alkyl halides that can be derived. When third intoxicants are reacted by a strong acid. a simple supplanting reaction occurs. The hydroxyl group of the third intoxicant is replaced by the available halide anion. provided by the strongly acidic environment. in order to organize alkyl halides and H2O. It besides intends to bring forth a merchandise to the purest possible potency with the usage of the procedure of simple distillment.

Experimental Detailss

In the experiment. the usage of a reaction between a strong acid and an intoxicant was used in order to synthesise an alkyl halide. Two parts were executed in the experiment. The first one involves the derivation of tert-butyl chloride from tert-butyl intoxicant with the usage of HCl. The 2nd portion involves the purification of the synthesized tert-butyl chloride. All necessary stuffs and lab setup were prepared. In a dry 30-milliliter separatory funnel. 10 millilitres of tert-butyl intoxicant and 20 millilitres of cold concentrated hydrochloric acid ( HCl ) were added. The mixture was swirled gently. doing certain that the mixture is non agitated excessively much. While the mixture was being swirled. the turncock was opened from clip to clip in order to alleviate the internal force per unit area which builds up inside the separatory funnel. After the two compounds are sufficiently combined. the mixture was set aside for approximately 20 proceedingss. doing certain that it would non be disturbed. After the needed clip has elapsed. the beds were separated which was facilitated by the usage of 3-5 millilitres of Na chloride ( NaCl ) solution. Once that measure has been executed. the lower bed of the mixture was drained and the aqueous later was discarded.

Figure I. Separatory Funnel Set-up

The organic bed within the mixture was transferred into a dry flask which contains a minute sum of Na hydrogen carbonate ( NaHCO3 ) . The flask. which contains the organic bed with NaHCO3. was swirled gently finally decanted into another dry flask. The filtrate which was collected was dried by the add-on of a little sum of anhydrous Ca chloride ( CaCl2 ) . The mixture was decanted into a dry 25-milliliter unit of ammunition underside flask. A few pieces of boiling french friess were added to the decanted mixture. doing certain the mixture was cool before those were added. The rough tert-butyl chloride was being prepared for distillment.

Figure II. Separation of Layers

Once the tert-butyl chloride is synthesized. a simple distillment set-up was employed in order to force through with the purification procedure. The pupils were cautious in doing certain that the H2O flowed into the underside of the condenser’s chilling jacket and out from the top. Besides. a thermometer bulb was placed merely below the side arm of the distillment caput. A unit of ammunition underside flask was utilised and it was filled to about ? of its volume. An ice bath was used in order to modulate the temperature of the distillment set-up. Once the sample was placed inside the flask. the H2O supply was turned on. doing certain that the H2O flow is uninterrupted within the capacitor and the land glass articulations suiting good. The sample in the flask was so gently headed to a soft furuncle. The temperature reading on the thermometer was observed intently. At some point. the temperature will stay changeless which signifies the sample has reached the boiling point which was recorded by the pupils. The vapour and condensate which passed through the side arm and into the capacitor. where most of the vapour will distill into liquid due to the cool H2O which flows into the chilling jacket.

Most of the vapour that has condensed into liquid finally drips into the arranger taking to the receiving flask. The fire was besides adjusted in a manner to minimise the sum of distillation. to 2 beads per second at most. in order to modulate the distillment procedure. The first 1 millilitre or 10 beads of distillation was discarded since those are considered as drosss within the sample. The fraction that is distilled when it reaches a changeless temperature is the one which was collected. taking into consideration that it must non be distilled until the sample becomes dry. Finally. when the sample started to boil. the heat beginning was so removed and the full set-up was allowed to chill before leveling the set-up. The pure tert-butyl chloride was collected in a 10-milliliter calibrated cylinder was cooled in an ice bath in order to minimise its vaporization since it is extremely volatile. The fraction that was distilled at around the 49-52°C was the one which was collected. It was eventually submitted to the teacher after reassigning it to a labeled phial.

Figure III. Simple Distillation Set-up

Consequences and Discussion

The experiment allowed the pupils to synthesise tert-butyl chloride. an alkyl halide which was formed from the add-on of a strong acid to an intoxicant. The belongingss of the synthesized tert-butyl chloride are as follows: |Properties | |Mass |0. 692 g | |Molecular Weight |92. 45 g/mol | |Density |0. 865 g/mL | |Mmol |7. 485 mmol | |Volume |0. 8 mL | |Color |Colorless | |Solubility
|Insoluble | |Boiling Point |47. 0°C |

After the executing of the experiment. the theoretical output for the synthesized tert-butyl chloride was computed. The value of the percent output of the derived alkyl halide was ___________ . Synthesizing alkyl halides for this experiment involves the reaction through the direct contact of the third intoxicant with the strong acid. with strength and stableness provided by the halogenic feature of the acid. The merchandise formed from this method of synthesis of alkyl halides is of increasing stableness with the diminishing atomic Numberss. viz. . RF & lt ; RCl & lt ; RBr & lt ; RI. The synthesis of alkyl halides with the public-service corporation of third intoxicants is the most appropriate for this since third intoxicants react readily with other reagents. The usage of primary and secondary intoxicants is non recommended for this instance since they react less readily. therefore. bring forthing a longer reaction clip which is non contributing for the clip allotted for the experiment. The equation for the synthesis is given below:

This sort of reaction is called a nucleophilic aliphatic permutation. It is one of the reactions which contributes to the field of organic chemical science. It involves the reaction between a nucleophile. which acts as an negatron brace giver. and an electrophile. an negatron brace acceptor. For an sp3-hybridized hybridized electrophile. a go forthing group is required in order for the reaction to continue. One illustration that will foreground this reaction is the synthesis of an alkyl halide from an intoxicant. Nucleophilic permutation is a reaction which is common for aliphatic compounds in which the go forthing group is attach to a C which is sp3 – hybridized. The mechanism for this man-made transmutation depends largely on the construction of the alkyl group which generates the go forthing group. Two tracts for the mechanism which may use for the permutation reactions include SN1 and SN2 reactions. SN1 reactions involve polar protic dissolvers. such as intoxicants. while SN2 reactions involve polar aprotic dissolvers such as propanone. In the experiment. an SN1 reaction proceeded since it utilized tert-butyl intoxicant. a third intoxicant.

A faster reaction would take topographic point since it merely involves one measure and because both the nucleophile and substrate are already involved in the rate finding measure. This produces both a cation and an anion during the reaction. These contributes to the comparative stableness of the charges on the ions formed during solvation. Molecules of compounds that have highly stable cations undergo SN1 mechanisms. Normally. merely compounds which produce third carbocations undergo SN1 instead than SN2 reactions. For this instance. it would be easy seen as to why the reaction was considered as SN1. The stableness of carbocations of third alkyl halides is accounted for by the original molecules which exhibit steric hinderance on the rear lobe of the bonding orbital. suppressing SN2 reactions from happening. The aforesaid happens the other manner around for SN1 reactions. With the contact between the proton ( H+ ) derived from the acid and the tertiart intoxicant within an elevated temperature it produces a reaction wherein the OH group in the intoxicant is acknowledged as the go forthing group. The OH group. along with the H+ . unite together to organize H2O and the carbocation intermediate.

The carbocation is attacked by the free Cl anions within the aqueous solution which consequences to the formation of tert-butyl chloride and H2O.

The processs for the experiment were followed purely. But along the manner. there were bounds which have contributed to some failures before accomplishing the coveted merchandise. One mistake done was the add-on of the higher edge sum of NaCl solution have resulted in some white precipitate to execute within the separatory funnel. This may good hold limited the sum of organic bed that could hold formed and separated which can account for the lower percent output of tert-butyl chloride. This may besides hold affected the pureness of the alkyl halide which added to the troubles experienced by the experimenters since they had to purify it non merely one time. But still. some stairss were executed in order to assist relieve the state of affairs.

One of those is the add-on of surplus of the concentrated HCl in order to. at least. warrant the opportunities of the reaction forcing through. It besides drives the reaction in a manner to to the full optimise the formation of an alkyl halide. With the add-on of HCl. it besides increases the sum of H+ which prevents the formation of other tert-butyl side merchandises which act as drosss and may impact the percent output of the experiment. Besides. the presence of big figure of H+ prevents the formation of tert-butyl side merchandises. In add-on to those. the usage of cold HCl alternatively of warm HCl since cold HCl prevents the desiccation of tert-butyl intoxicant to isobutylene. ( CH3 ) 2C=CH2. which is a consequence of increased temperature.

Another measure taken in order to guarantee the success of the experiment was during the distillment portion wherein solid Na hydrogen carbonate ( NaHCO3 ) was used in order to extinguish extra H+ in the concluding aqueous merchandise. Furthermore. it would be much easier to pour neutralised H+ compared to solid Na2CO3. Solid NaHCO3’s other intent was to neutralize HCl sufficiently since extra HCl was added in the first portion in order to optimise the success of the reaction.

Tert-butyl chloride. one time synthesized. should non be exposed to a batch of H2O because it may hydrolyse and turn it back to intoxicant. Besides. another thing that would forestall the hydrolysis of tert-butyl chloride would be drying it with Ca chloride ( CaCl2 ) before distillment. If it did non undergo drying. distillment would transfuse the halide with wet which will hydrolyse it. Even before distillment. the merchandise was already dried with the usage of anhydrous CaCl2 in order to minimise the sum of H2O and untreated intoxicant which may impact the consequences of the distillment of tert-butyl chloride.

Another built-in portion to the success of the distillment procedure is the uninterrupted flow of H2O within the capacitor. The condensation of the liquid sample within the capacitor procedure requires an equal or. if possible. extremely cool H2O flow within the capacitor. If the H2O flow is deficient or discontinuous. this may ensue in the low efficiency of distillment of the liquid sample due to the decreased chilling capableness within the capacitor.

Returning to the synthesis of tert-butyl chloride. the free hydride ( H- ) which remains within the aqueous solution may besides respond with the carbocation intermediate before it reacts with the chloride anion in the solution. The formation of tert-butane as a merchandise may be a possible side reaction for the synthesis of tert-butyl chloride with usage of strong acids in handling third intoxicants. The synthesis of tert-butyl chloride involves the reaction of a tert-butyl carbocation intermediate. It may undergo the procedure of elminiation of a beta H in order to bring forth 2-methypropene as a side merchandise. Whenever intoxicants are treated with strong acids. the OH group alterations as it becomes more protonated. therefore. potentially altering it to a better go forthing group. as H2O. which can be substituted by the come ining halide.

A little sum of its protonated signifier may lose H2O which may so organize the free carbonium ion which readily stabilizes by organizing an olefine subtraction a proton at the 2nd C. This is normally a minor merchandise formed because primary carbocations which are free in the solution are unstable. The loss of H2O along the coincident onslaught would be more favorite. Although. this may be the instance. it can be detached easy with distillment because olefines have lower boiling points compared to alkyl halides. Removal of the side merchandises. which act as drosss during distillment. can hence be done easy. The inclusion of the side reactions’ merchandises with the chief merchandise. tert-butyl chloride. may ensue in the inaccuracies reflected on several physical belongingss when compared to the purified sample such as the boiling point. In order to guarantee more accurate consequences in wining tests with its synthesis. some thoughts must be taken into history.

For the experiment to be more accurate in wining tests. some recommendations and points should be taken into consideration. The synthesis of the pure tert-butyl chloride was really low. bring forthing merely 7. 38 % . A possible ground behind the low output could be dividing the different laters within the separatory funnel. Separating the aqueous bed. which was used for the experiment. from the t-butyl bed leaves a batch of room for t-butyl to be accidently discharged from the solution alongside the aqueous subsequently. In add-on to that. if the anhydrous CaCl2 added is deficient. it may waterlog the sample and increase the mensural mass of the merchandises. This can take to the inaccurate premise that more merchandise was synthesized.


Because of the resulting output of 7. 38 % . it can be concluded that side reactions involved were non minimized. Besides. some stairss along the manner may hold affected the per centum output such as the add-on of more NaCl than the least possible sum to be added. the less sum of organic bed that has been derived from the separatory funnel and the sum of distillation that have been thrown out due to the drosss combined from the petroleum sample. In add-on to that. the simple distillment set-up may non certainly optimise the sum of tert-butyl chloride that can be acquired. One of the experimenter believes that some mechanisms and stairss can still be taken in order to better its output. One of the chief failings of the manner the experiment was handled was the clip consumed and the velocity at which the experimenters performed the experiment. A fast and efficient executing of the experiment can cut down the hazard of allowing side reactions occur during the length of the experiment. Another recommendation is to rinse the receiving flasks with cold intoxicant since H2O would non go an agent of a side reaction.

By the terminal of the experiment. despite the many failures that the experimenters have faced in synthesising the alkyl halide from intoxicant. they managed to convey it into fruition. The aims of the experiment were satisfied: tert-butyl chloride was successfully synthesized from tert-butyl intoxicant with the usage of HCl which acts as the H halide. Purification techniques were mastered due to the legion failures which were encountered along the manner. Some notes on the processs. such as the sum of reagent that must be added. can be changed in a manner in order to optimise the sum of yielded distillation. Despite the failures faced along the manner. the experiment was deemed to be a success.


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Chemical Land Co. ( 1998 ) . Tert-butyl chloride. Retrieved April 28. 2009 from: hypertext transfer protocol: //chemicalland21. com/industrialchem/organic/tert-butyl % 20chloride. htm


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