UNIVERSITI TUNKU ABDUL RAHMAN FACULTY OF SCIENCE KAMPAR CAMPUS PERAK BACHELOR OF SCIENCE (HONS) BIOTECHNOLOGY YEAR 1 SEMESTER

2 UDEC 1164 ORGANIC CHEMISTRY EXPERIMENT 6 : PREPARATION OF n-BUTYL ETHYL ETHER FROM 1-BUTANOL LECTURER : DR.YIP FOO WIN STUDENTS NAME STUDENTS ID LAB PARTENERS HAMSAVATHANI A/P SELVAN 1207190 1. 2. 3. 4. THANAPRIYA A/P SEKAR CRYSTAL TOH CALLIE CHEAH ENG CHEW SHIVASNI JAGANATHAN

Title: Preparation of n-Butyl Ethyl Ether from 1-Butanol Aim: - To prepare n-butyl ethyl ether from 1-butanol - To understand mechanism involved in the reaction. Introduction: The experiment is divided into two parts. The first part involves the formation of n-butyl bromide from 1-butanol while the second part of the experiment, the n-butyl bromide produced in the first part is being converted into n-butyl ethyl ether by using methanol and sodium hydroxide. The mechanism of synthesis of ether is also known as mechanism of Williamson ether synthesis. Apparatus and Materials Round-bottomed flasks (50 and 250 cm) Bunsen burner Condenser Thermometer Separating funnel Sodium bromide 1-butanol Conc. sulphuric acid Anti-bumping granules 5% aqueous sodium bisulphate Distilled water 10% aqueous sodium carbonate Anhydrous calcium chloride Sodium hydroxide 95% ethanol n-butyl bromide anhydrous magnesium sulphate

Procedure: n-Butyl bromide 1. 27g of sodium bromide, 30cm of water and 20cm of 1-butanol are placed into a 250cm round bottom flask. 2. The mixture is cooled in an ice bath 25cm conc.sulphuric acid is added with continuous swirling. 3. Added three anti-bumping granules and attached with a gas trap to prevent HBr escaping, the round bottom flask is heated vigorously under reflux for 1.5 hours. 4. Allowed the mixture to cool and set up the apparatus for distillation. 5. Distilled the two layered mixture until the temperature reaches the boiling point of water. 6. The distillate is transferred to a separating funnel and shakes with an equal volume of 5% aqueous sodium bisulphate.

Result : The solution becomes blue-black when continuously swirling with cocn.sulphuric acid. CH3CH2CH2CH2OH + NaBr + H2SO4 CH3CH2CH2CH2Br + NaHSO4 + H2O

Therefore, 1 mole of NaBr reacts with 1 mole of 1-butanol to produce 1 mole of butyl bromide. The second session was failure.

Discussion: The determination of this experiment is to produce n-butyl ethyl ether via substitution reaction and to purify it using simple distillation where substances with different volatility and boiling points are separated from each other. In the experiment, the primary alkyl halide n- butyl bromide can be prepared easily by allowing 1-butanol to react with sodium bromide and sulphuric acid. The sodium bromide reacts with sulphuric acid under reflux to produce hydrogen halides. The chemical reaction indicates that the hydrogen halide is produced from the reaction.

2NaBr + H2SO4

2HBr + Na2SO4

The hydrogen halide produced is used to convert 1-butanol to become butyl bromide by undergoes nucleophilic substitution. Sulphuric acid speed up the reaction by producing a higher concentration of hydrobromic acid and protonates the hydroxyl group of 1-butanol so that water is displaced rather than the hydroxide ion OH-. The acid also protonates the water as it is produced in the reaction and deactivates it (water) as a nucleophile, hence the water keeps the butyl bromide from being converted back into the alcohol by nucleophilic attack of water. The distillate is presented with same approximate same amount of sodium bisulphate,NaHSO4, after the reflux process. The determination of adding of bisulphate is used to absorb water from, the organic solvent since it has high hydrophobic property. Sodium carbonate (mild acid) is added to neutralize the acidic solution. Anhydrous calcium chloride is added as drying agent to absorb water droplets in order to purify the organic layer. Excess drying agent used to ensure that all the water in solvent is removed. If the water remains in the materials collected, it could be interfere with the analysis. After filter out the drying agent, several anti bumping granules( boiling chips) are added to prevent over boiling during distillation. Distillation process is carried out to purify the butyl bromide in the range of temperature 90C to 105C. The pure n-butyl bromide is obtained in the distillation process. Reference: 1. http://www.britannica.com/EBchecked/topic/193965/ether, Retrieved on 2nd March,2013.

Questions: 1st practical session 1.substitution 2. nucleophile 3. 4.

2nd practical session 1. 2. 3.