Deuterated phenylethanes

Deuterated phenylethanes were observed in the region from 3100 to 2000 cm. All aliphatic C-H and C-D stretching vibrations could be assigned. 

The VCD spectra of molecules of the form CH3C HR,R2 have been investigated in the CH stretching region (20, 57-59) and the 16(X)-900-cm mid-infrared region (59, 60). The ROA of this type of molecule has also been recorded (II-14). In particular, a-deuterated ethanol and a-phenylethane derivatives have been studied. 

Treatment of l-bromo-2-deuterio-2-phenylethane with strong base leads to a mixture of deuterated and nondeuterated phenylethylenes in an approximately 7 1 ratio. Explain. 

Reaction of l-bromo-2-deutero-2-phenylethane with r -r-butoxide in iifri-butyl alcohol gives a 7 1 ratio of deuterated and nondeuterated phenylethenes. Write the structures of the products. What does the data surest about the ease of abstraction of deuterium versus hydrogen ... 

---