14. An organic student Naph T. Ene attempted to Convert tert-butanol (8) into te

Question

14. An organic student Naph T. Ene attempted to Convert tert-butanol (8) into tert-butyl chloride (9). Unfortunately GC, as shown below, indicated the reaction Was incomplele. However, Naph did obtain 1.5g of tert-butyl chloride. a. Label each peak in the gas chromatogram as 8 or 9. Place the numbers in the boxes above the peaks. (2 pts) Assume Naph's GC column was the same as the column you used in your GC experiment this semester. b. Calculate the theoretical yield for tert-butyl chloride. The other product Is H2O. c. Calculate the % yield for tert-butyl chloride.

Explanation / Answer

a) If the GC column is reversed phase (non polar stationary phase), then the more polar compounds will elute first. Then in that case, 8 will be the peak at lower retention time.

If the GC column is normal phase (polar stationary phase), then the compound 8 will elute last.

b) The theoretical yield would have been achieved if just one peak was observed in the chromatography with an area of 24+45 = 69 .

1.5g of product was obtained = 0.0162 moles of product.

If the product was the peak of area = 24 (reversed phase case) , then the theoretical yield would have been (69*1.5) / 24 = 4.31g . In the norlam phase case, the theoretical yield would have been (69*1.5) / 45 = 2.3g

c) The % yield is , if we are in case of reverse phase = 100*( 24/69) = 34.78%

if we are in case of normal phase = 100*( 45/69) = 65.2%

Whether to be in reverse or normal phase case, depends on the GC column you have used in the lab and it is not specified in the question! I hope It would have helped you ! :)

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