The Noyori asymmetric hydrogenation of ketones is a chemical reaction for the en

Question

The Noyori asymmetric hydrogenation of ketones is a chemical reaction for the enantioselective hydrogenation of ketone, aldehydes, and imines. This reaction exploits using chiral ruthenium catalysts introduced by Rypji Noyori. He shared half of the Nobel Prize in Chemistry in 2001 with William S. Knowles for the study of the asymmetric hydrogenation. BINAP/diamine-Ru catalyst is used for the asymmetric hydrogenation of simple ketones. These hydrogenations are used in the production of several drugs, such as the antibacterial levofloxin, the antibiotic carbapenem, and the antipsychotic agent BMS181100. Reduction of acetophenone to 1-Phyenylethanol with Noyori's BINAP/diamine-Ru catalyst resulted in an a mixture of the alcohol enantiomers. The reaction was performed on 3.85 g of acetophenone and produced the alcohol products in 95% overall yield. The entire product was dissolved in 75 mL and analyzed by polarimetry in a 3 dm polarimeter tube. The observed rotation was -1.4 degree. What is the optical purity of the product? What is the enantiomer composition of the product (%+ and %-) given that the specific rotation of enantiomerically pure 1-Phyenylethanpl is 10 degree? Based on the fact that (R)- 1:Phyenylethanpl is the levorotatory enantiomer, draw the major enantiomer that [formed with the stereochemistry explicitly shown.

Explanation / Answer

(R)-1-phenylethanol in about 80% ee will be the major product with the provided details.

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