Discussion Of 1-Butanol Into 1 Bromobutane

7) Discussion:
The goal of this experiment was to covert 1-butanol into 1-bromobutane. By reacting 1-butanol with bromine, a nucleophilic substitution would occur where the alcohol group from 1-butanol is replaced with a bromine. In order for the -OH group to depart, its conjugate acid would have to be a strong acid. The conjugate acid for a hydroxyl group is water, which is a weak acid. To get the reaction to occur, 1-butanol would have to be reacted with sulfuric acid to protonate the -OH group. The leaving would then be a water, with a conjugate acid of hydronium (H3O+), which is a very strong acid. The reaction would then follow either the SN1 or SN¬2 mechanism. The SN1 mechanism is characterized by two steps. The first is heterolytic cleavage, where the leaving

Then the nucleophile can attack the carbocation to form the final product. The SN¬2 mechanism is characterized by simultaneous attack of the nucleophile and departure of the leaving group. The nucleophile would attack the carbon on the opposite side of the leaving group forcing the bond between the leaving group and carbon to break resulting in the departure of the leaving group. Since the nucleophile will attack from the opposite side, an inversion of stereochemistry is seen. For the reaction of 1-butanol with bromine in the presence of sulfuric acid, the carbon with hydroxyl group contains two hydrogens which are really small atoms, so the molecule can easily undergo the SN¬2 mechanism because there is no steric hindrance preventing the nucleophile to attack from the opposite side of the leaving group. With the mechanism understood, the experimentally was able to be performed by mixing about 5.55 grams of NaBr with 5mL of water and 5mL of 1-butanol and mixed thoroughly. Then the sulfuric acid was mixed slowly into the solution with the flask in an ice bath since the acid-base reaction is exothermic, which generates heat. With the reaction set, the solution was then prepared for