Organic chemistry lab report - Preparation of alkyl chloride by sn1
Methods and Background
In this lab we observed the conversion of a tertiary alcohol, (CH3)3COH, into a tertiary alkyl chloride, (CH3)3CCl, using hydrochloric acid. This reaction occurs via nucleophilic substitution of one group for another group. In this case, -Cl group was substated for an -OH group. We tested the presence of this compound by performing sodium iodide and silver nitrate tests.
There are two different kinds of nucleophilic substitutions: Sn1 and Sn2. Which mechanism a compound might go through depends largely on the structure of the alkyl group bearing the leaving group. Leaving groups are usually basic groups like Cl- or H2O and the nuleophile usually has a pKa value less than 5. Sn1 undergoes one order of kinetics. This means that the reactant takes part in the rate determining step, or the slowest step, of the reaction. During Sn1 mechanism, the reactant protinates itself and forms a stable leaving group. The leaving group is kicked out d
In this experiment, we obtained 3.4 grams of organic layer, tert-butylchloride, after simple distillation. This experimental mass was only 35.1% of the original product. Multiple factors like improper separation of the organic and the aqueous layer, and boiling off the organic layer might have resulted in this low yield of the sample. When we separated the organic layer from the aqueous layer we might have poured in some of the organic layer into the beaker with the aqueous layer. Thus, some of the organic layer was not distilled via simple distillation and that difference in mass was not taken into consideration when we measured the experimental mass of tert-butylchloride. Furthermore, tert-butanol has a boiling point of 83oC, so it some of the tert-butanol was still mixed with