Production of Triphenylmethyl Bromide and Triphenylmethyl Methyl Ether from Triphenylmethanol with the Use of Sn1 Reactions

Production of Triphenylmethyl Bromide and Triphenylmethyl Methyl Ether from Triphenylmethanol with the use of SN1 Reactions

Experimental Section

Triphenylmethyl Bromide. Before the start of the experiment a hot water bath was prepared, so it would reach boiling by the time it was needed in the procedure. Triphenylmethanol (0.238 g, 0.795 mmol), acetic acid (4 mL), and 47% hydrobromic acid (0.6 mL, 0.4 g, 5 mmol) were placed in a rxn tube. The mixture of these three produced a bright yellow color. This rxn tube was then heated in the boiling water bath for approximately 5 min, where a slight color change occurred from bright yellow to a lighter yellow. An ice-water bath was used to cool the rxn tube for approximately 10 min allowing product to form. Vacuum filtration was used to collect the crude product. The crude product was washed with ½ a pipette of both water and hexanes the wash caused another color change it was now white. After it was dry the crude product (0.219 g) was weighed. With the use of hexanes the product was recrystallized and yielded triphenylmethyl bromide (0.135 g, 0.481 mmol, 45.7%). Beilstein test was used to determine if the product contained bromide. The coper wire dipped in the product produced a flame that burned orange, then a blue/green color, and then just burned green meaning the product contained bromine.

Triphenylmetyl Methyl Ether. Triphenylmethanol (0.224 g, 0.860 mmol) and sulfuric acid (2.0 mL) were added to a rxn tube and stirred to help dissolve. The mixture of these two produced a dark yellow color. This mixture was then transferred into a rxn tube that contained ice-cold methanol (2.0 mL). Crystals had not formed, so the rxn tube was placed in an ice-water bath for approximately 5 min. When substantial amount of crystals were formed, they were collected by vacuum filtration and washed with water the sample was now white. After it was dry the crude product () was weighed. The product was recrystallized with hot...