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1-bromobutane is a primary alkyl halide (primary alkyl) and therefore it is produced from bimolecular nucleophilic substitution reactions (Sn2). Figure 1 shows the reaction for the synthesis of 1-bromobutane. Figure 1. Global reaction for the synthesis of 1-bromobutane.
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- Objective
- Background
- Experimental Procedure
- Physico-Chemical Properties
- GHS Pictograms
- International Chemical Identifier
- References
To produce n-butyl bromide from n-butyl alcohol, and to demonstrate the ability to carry out a substitution reaction in organic chemistry, specifically the conversion of an alcohol to an alkyl halide.
Reacting a primary alcohol with a hydrogen halide produces a primary alkyl halide. The reaction follows an SN2 mechanism, as the dehydration step is competitive. The reaction requires a strong acid to protonate the hydroxyl group. Aqueous HBr, HI or HBr gas can be used. In this experiment, the HBr is generatedin situ by reacting NaBr with H2SO4. Na...
In a 250 ml round-bottom flask, place 30 g of sodium bromide and 30 ml of water. Shake the flask until most of the salt has been dissolved. Add 18.5 g of butan-1-ol, and cool the flask to 5–10 ºC in an ice bath. Slowly add 25 ml of concentrated H2SO4. Place the flask with a reflux condenser and a trap adapted for gases containing NaOH solution (aqu...
This table collects data for the molecular weight (Mw), melting point (M.p.) boiling point (B.p.) and density of the reactives and compounds used in this laboratory experiment.
Hazard pictograms form part of the international Globally Harmonized System of Classification and Labelling of Chemicals (GHS) and are collected in the followinf Table for the chemical compounds used in this experiment.
The IUPAC InChI keyidentifiers for the main compounds used in this experiment are provided to facilitate the nomenclature and formulation of chemical compounds and the search for information on the Internet for these compounds.
Isac-García, J.; Dobado, J. A.; Calvo-Flores, F. G.; and Martínez-García, H. (2015). Experimental Organic Chemistry Laboratory Manual. Elsevier Science & Technology. ISBN: 978-0-12-803893-2Vogel, A.I., Furniss, B.S., Hannaford, A.J., Tatchell, A.R., and Smith, P.W.G. (1989). Vogel’s Textbook of Practical Organic Chemistry (Vogel’s Textbook series). Longman. ISBN: 9780470214145Jun 18, 2020 · The limiting reagent in this reaction is 1-butanol. The balanced equation shows that one mol of 1- bromobutane is obtained for every mol of 1-butanol used. Since we are starting with 2.5 mmoles of 1- butanol, then the theoretical yield of 1-bromobutane is also 2.5 mmoles, or .342 g.
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NaHCO3 + H- H2CO3 (aq) + Na+ Carbonic acid further dissociates into carbon dioxide and water. H2CO3 (aq) H2O (l) + CO2 (g) 2. 3. Determine the limiting reagent. The limiting reagent in the reaction for the synthesis of 1-bromobutane was 1-butanol. 4. Calculate the theoretical yield. The theoretical yield of the reaction was 1 grams.
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1-Bromobutane is the organobromine compound with the formula CH 3 (CH 2) 3 Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble in organic solvents. It is primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide.
- 101.4 to 102.9 °C; 214.4 to 217.1 °F; 374.5 to 376.0 K
- −112.5 °C; −170.4 °F; 160.7 K
- C₄H₉Br
- 137.020 g·mol−1
3. Formation of 1-bromobutane. 1. In a 100 mL round bottomed flask, place 13.3 g of NaBr (129 mmol, ~18% excess), 15 mL of water and 10 mL of butan-1-ol (109 mmol). 2. Cool the mixture in an ice bath and, slowly and with continuous stirring, add 11.5 mL of concentrated H. 2.
The product will be verified by gas chromatography by comparing the chromatograms of the starting material, 1-bromobutane standard, and your product. Confirmation of your product, 1-bromobutane can also be performed by reacting the product with a solution of sodium iodide in acetone. The primary alkyl halide will react by means of an S N 2 ...
