n-Butyl bromide from n-butanol

Kella Ortega, Miguel Fernandez, Andrei Maghirang

Experiment performed July 1, 2013; final report submitted July 22, 2013

Abstract
A second order substitution reaction was done on an n-butyl alcohol to form an n-butyl

bromide. The product made was a slightly milky white liquid solution, even though 1-

bromobutane is supposed to be colorless. The product was analyzed through infrared

spectroscopy and the results of the analysis showed that 1-bromobutane (n-butyl bromide) was

present in the product. The results from the infrared spectroscopy, however, should not be seen as

absolute since there are still many tests that have yet to be done on the product (melting point,

density, etc.) in order to prove its identity.

Introduction

Substitution reactions usually involve the breaking of a sigma bond between a carbon and

a certain atom, usually a halide, and the same carbon forms a bond with a different atom, usually

a nucleophile. This reaction is very useful to study because it is a reaction that occurs in

biological systems. In fact, it is also involved in the methyl groups in S-adenosylmethionine,

which is used to treat tuberculosis6.
The n-butanol underwent a second order substitution reaction to form n–butyl bromide6.

Figure 1:

SN2 Reaction;

formation

of 1-

bromobutane

while oxidizing and reducing agents are highly reactive to it1. Second order substitution reactions only involve one step. It appears as a colorless liquid that may dissolve in ethanol and diethyl ether1. In this reaction. 1-bromobutane. is a compound that can be used to generate carbon- carbon bonds by having it react with magnesium metal in dry ether. It is usually generated in enclosed systems where butyraldehyde undergoes catalyzed hydrogenation and distillation. the same side as the leaving group. acids. In the experiment. opposite side to the leaving group. N-butanol is a chemical that acts as a reactant when it is used to generate formaldehyde and as an industrial intermediate to form butyl acetate and other butyl esters. A bond is broken and another is formed in just one step in this reaction. The final product. 2 . Organic materials. the bromide ion. the leaving group (Figure 1). 1-butanol is a molecule that is kept intact by intermolecular hydrogen bonds because of the O-H bond and it exhibits dipole-dipole interaction and Van-der Walls force because it is a polar and bent6. or the backside. forms a bond with the carbon atom that is breaking its bond with the OH group. and alkalis are slightly reactive to this compound. a nucleophile can either attack from the front side. and this would determine the stereochemistry of the final product. the nucleophile. The rate of this type of substitution reaction depends on both the alkyl halide and the nucleophile6.

bromide ion. the mixture underwent distillation 3 . At the last part of the reaction. The whole experiment involves a lot of different chemicals. While sulfuric acid was being added. After which. It was then cooled in an ice bath. sodium hydrogen sulfate. at the first part of the reaction. a carbon atom with an OH function group is attacked by the bromide ions from the Hydrogen Bromide product from the previous reaction. Hydrogen Bromide and Sodium Hydrogen Sulfate were formed through the reaction of Sodium Bromide with Sulfuric Acid.9-mL of 1. it was also being swirled while 8. This attack would result to the separation of the -OH function group. To expound. it was heated under reflux. Methodology A combination of 9 grams of sodium bromide. the resulting Hydrogen Bromide dissociated. and a bromobutane and a hydroxide ion was formed. This hydrogen ion would then bond with another H+ ion to form H2O. Then the Hydrogen Bromide formed at the first part of the experiment was oxidized by concentrated Sulfuric Acid by the reaction of Sulfuric Acid to Sulfuric Dioxide gas. a noticeable increase in temperature was observed. there was a short period of time wherein a slight tint of yellow was seen as the acid was added. An electric stove with a water bath was used for the reflux. Also. 10-mL of water. In 1-Butonal.butanol was mixed into a 100-mL boiling flask. After undergoing reflux. Different compounds were formed as the different reactions occurred to form the 1-bromobutane. hydrogen bromide. sulfur dioxide gas and a hydroxide ion were formed. The flask was connected to a condenser and for 30 minutes. This resulted to Hydrogen Bromide's oxidation to Bromine molecule. As it was being cooled. and 6.0-mL of concentrated sulfuric acid was added. This would result to the mixture of Butoxybutane and 1-Butene5. In total. a lone pair on the -OH function group was attacked by sulfuric acid.

The group was unable to test and see the physical properties of the product made. Cel.89. 10-mL of water was added to the organic layer. inverted. The peaks ranged from 842. Its molecular weight was supposed to be 137. The upper layer was clearer compared to the other white layer found at the bottom. anhydrous calcium chloride was added to the organic layer until the solution started to turn clearer or more translucent4. The temperature during distillation ranged from around 70 .02 g/mol. In the Erlenmeyer flask.4. The physical properties the product (1-bromobutane) was supposed to have exhibited as according to theory is a -112 deg. Another separatory procedure was done. Cel.until no more water-insoluble material was seen flowing in the water. a density of 1. a boiling point of 100-104 deg Cel.276g/mL at 25 deg. and a water solubility of 0. Once it was extracted. the distillate was placed inside a separatory funnel where 25-mL of water was added to it.27 up to 3383. In this separatory procedure. After separating the two layers and extracting the lower layer. After undergoing distillation. it was returned to the separatory funnel again where 8-mL of a 10% aqueous sodium bicarbonate solution was added. a freezing point of 23 deg. Cel. This time separation was done with the addition of 7-mL of concentrated sulfuric acid instead of water. the organic layer is the upper layer. 2 There were 15 peaks that were found when the product was run through an IR spectrum. Cel melting point. It was stoppered. Once the layers were separated. The peak that was found at the start of the 4 . and shook. Two layers appeared.608 g/L at 30 deg.90 deg. the upper layer was also transferred to another container just in case the organic layer was not properly identified. However. It underwent separation once again and the lower organic layer was taken once again for another step of separation. The lower layer was drawn-off. the organic layer was drawn into an Erlenmeyer flask.. Cel.

This step however has not fully separated the product needed from the rest of the mixture. the result of the distillation was placed in 5 .27 up to 1401. the mixture was placed under distillation in order to take out the liquid 1-bromobutane of from most of the sodium salts and the sulphuric acid. The product that was found in the experiment was 99% 1-Bromobutane which was the expected product for this experiment. 10-mL of water. The 11 peaks found close together at the end of the spectrum ranged from 642.butanol was placed in an ice bath to decrease the mixture's increase of temperature once the sulfuric acid was to the mixture.07 which would be more or less P-O. After finishing the reaction with sulfuric acid.93 which would more or less be C-O. 1-butanol. The three peaks that were found bundled together in the middle of the spectrum ranged from 2872.9-mL of 1. namely water. the group was able to produce the stated product. in which its -OH group will be replaced by a -Br group. After undergoing reflux. and some sulphuric acid.spectrum numbered at 3383. By decreasing the temperature of the mixture when it reacts with the sulfuric acid. swirling the mixture to make the reaction happen faster became possible. In order to remove most of these. the mixture consisting of 9 grams of sodium bromide.85 up to 2981. the flask was connected to a condenser and was heated for 30 minutes under reflux. In the experiment. According to the results from the IR spectroscopy. Results and Discussion The main objective of this experiment was to produce 1-bromobutane by having 1-butyl alcohol undergo an SN2 reaction. whose volatility has decreased.89 which would more or less be O-H. It took 30 minutes of heating because it would take a lot of time to break the covalent bonds in this mixture. and 6.

This is supposedly due to the droplets of water in the 1-bromobutane product4. The main error the group committed during the experiment was forgetting to place boiling chips inside the oil bath during the distillation procedure. The bottom layer was used for another separatory procedure. In this separation. Another distillation should have been done to the solution however. The 1-bromobutane that was extracted. the upper layers were both saved in other containers in case of some complication which may have made 1-bromobutane the upper layer4. For both separatory procedures. In this separation. no accident occurred. In this procedure. the product had a cloudy white shade. the lower layer was extracted and some anhydrous calcium chloride was added to dry it. The extracted 1-bromobutane underwent another separatory procedure. Another error the group made was that they judged the end of adding anhydrous calcium chloride too early. After the separation. it was noticed that unlike the expected clear coloring of 1- bromobutane. due to the time constraints. the bottom layer was thought of as the organic layer since 1 - bromobutane theoretically has a larger density (1. This time 10-mL of water was used. They should have kept on adding the drying agent until the solution was fully translucent and not just clearer than it was before. It was shaken and 2 layers appeared.276 g/mL) than the other layer of both mixtures. 6 .a separatory funnel with 25-mL of water. underwent a separatory procedure. not water like the previous separations. this procedure was not done. The boiling chips were only added once the oil started acting in a volatile manner however. once again. 7-mL of concentrated sulfuric acid was used. 8-mL of a 10% aqueous sodium bicarbonate solution was added to remove the acid that was dissolved in the 1-bromobutane. However. However. the upper layer was thought to be 1-bromobutane since its density is supposedly smaller than the sulfuric acid. however.

by not rushing one can avoid mistakes to help prevent the product loss and to increase the yield. No by-product was found alongside 1-Bromobutane. This result shows the expected product from the reaction. The IR spectrum also showed that the product lacked contaminants leaving it more or less a pure substance. Conclusion and Recommendations The n-butanol that went through a SN2 reaction produced n-butyl bromide whose IR spectrum showed 99% 1-Bromobutane. the experimenters were not able to run the products through any other tests to prove its identity. The IR spectrum also showed the peaks which we could identify as O-H. To prove the identity of the products and by-products. and proof of the success of the synthesis. The low yield would be caused by frequent transfers of the reaction mixture into the different glassware used. This is mostly due to the inefficient removal and repeated separation of the aqueous layers after washing. The experimenters recommend to not rush in doing the experiment. 7 . the experimenters ran the product through an IR spectrum which showed the product to be 99% 1-Bromobutane which was the expected product for this experiment. Other than IR spectrometry. C-O and P-O which are bonds that are supposed to be found on a bromobutane IR Spectra.

Organic Chemistry Lab Courses.) Smith.org/documents/sids/sids/71363. PubChem.ht ml 5.).com/ChemicalProductProperty_EN_CB2852782.htm 3.) n-butyl alcohol. (n.). Retrieved July 18. 7.). from http://www.).) Williamson. 8 . New York: McGraw Hill.pdf 4. (n. Organic Chemistry (3rd ed.gxnu.d. 2013.). (n. from http://pubchem. (n.d. K.nlm. from http://www. Organic Chemistry Lab Courses.).html 6.chemicalbook.ce. 2013.d. K.gov/summary/summary. Macroscale and microscale organic experiments (5th ed. R. Retrieved July 21. J. 2013. from http://www.) Preparation of 1-bromobutane.) butyl bromide.edu.edu. (n.) 1-Bromobutane. Retrieved July 21. IPCS INCHEM.cn/organic/net_course/content/bromobutane/procedure.) Preparation of 1-bromobutane. Minard. 2013.ncbi.inchem. (2007).ce.). 2013.d. Retrieved July 20. Retrieved July 21.cn/organic/net_course/content/bromobutane/content. (2011). Masters.References 1. from http://www.d..gxnu.nih. ChemicalBook.. Boston: Houghton Mifflin Company.cgi?cid=8002 2.

Appendices Appendix 1 – IR spectrum of liquid product 9 .