The specific rotation of a sample of mandelic acid [PhCH(OH)CO2H] is +12.5° and of pure R-(+)- mandelic acid is +158°. Calculate the (1) % optical purity, (2) ee, (3) % composition and (4) draw a clear stereo-structure for the enantiomer in excess
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The specific rotation of a sample of mandelic acid
[PhCH(OH)CO2H] is +12.5° and of pure R-(+)-
mandelic acid is +158°. Calculate the (1) % optical
purity, (2) ee, (3) % composition and (4) draw a clear
stereo-structure for the enantiomer in excess
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- The chiral hydroxyl compound P, C7H14O contains a five-membered ring and showspositive result in iodoform test. Compound P and sodium bromide can be produced byrefluxing compound Q with aqueous NaOH solution. Compound P is heated withbenzoic acid in the presence of concentrated H2SO4 to form a sweet-smelling product,compound R. Deduce the structure of P, Q and R. PLEASE PROVIDE CLEAR HAND WRITING AND SOLUTIONSThe specific rotation of (S)-carvone (at 20 degrees) is +61. A chemist prepared a mixture of (R)-carvone and its enantiomer, and this mixture had an observed rotation of -55. (a) What is the specific rotation of (R)-carvone at 20 degrees?Answer ALL parts of this question. Fluoxetine (Prozac) is an anti-depressant, sold as a racemic mixture with both enantiomers of equal activity. (S)-Fluoxetine has a specific optical rotation of +14.0°. F₂C. HO (S)-Fluoxetine (c) A laboratory mixture has 80% enantiomeric excess (ee) of (S)-fluoxetine. What percentage of each enantiomer is present in the mixture? (d) What is the observed specific rotation of the laboratory mixture in part (c)? (e) Draw the product of HCI reaction with (S)-fluoxetine.
- 8. The specific rotation of (S)-carvone (at +20°C) is +61. A chemist prepared a mixture of (R)-carvone and its enantiomer, and this mixture had an observed rotation of -55°. (a) What is the specific rotation of (R)-carvone at 20°C? (b) Calculate the % ee of this mixture. (c) What percentage of the mixture is (S)-carvone?The anti-inflammatory agent, (S)-naproxen sodium salt has a specific rotation of +66°. The commercial preparation of the latter agent results in a mixture that has a 97% enantiomeric excess (ee). Na Hooooja moo (S)-naproxen sodium salt (d) What percentage of each enantiomer is obtained from the above commercial mixture? H3CO (e) Provide a reaction scheme for the formation of the (S)-naproxen sodium salt from "acidic" (S)-naproxen.The specific rotation of (S)-carvone (at 20 degrees) is +61. A chemist prepared a mixture of (R)-carvone and its enantiomer, and this mixture had an observed rotation of -55. (a) What is the specific rotation of (R)-carvone at 20 degrees? (b) What percentage of the mixture is (S)- carvone? Choose from the following options. 1. 90% (S)-carvone and 10% (R) 2. 10% (S)-carvone and 90% (R) 3. 95% (S)-carvone and 5% (R) 4. 5% (S)- carvone and 95% (R)
- Answer ALL parts of this question. The structure shown below is that of one of the optical isomers of the well-known analgesic, ibuprofen: (a) (b) (c) CH₂ H₂C-A C H₂ 2048 ÇO,H CH CH₂ Explain how the Cahn Ingold Prelog sequence rules can be used to rank groups in order of priority, using the four groups attached to the chiral centre in ibuprofen as illustrated. Based on the order of priority of the four groups determined in part (a) of this question, explain which of the two enantiomers (R or S) of ibuprofen is shown. S Draw the structure of the enantiomer of this compound and comment on why it might produce a different reaction in vivo (in fact the enantiomer has no analgesic effect).3b) (i) Using Fischer projection, draw all the stereoisomers of 3-chloro-2-hydroxypentanoic acid. ii) Assign the chiral centre(s) with R/S configurations in part (b)(i). Indicate which areenantiomers, diastereomers and meso compounds (if any).Treatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.
- Thalidomide exists in two enantiomeric isomers as shown below. N (R) NI(S) O If a solution is prepared by adding a 50:50 ratio of two enantiomers what will be the expected observed rotation? Explain your answer in 1-2 sentences.(S)-carvone is an optically active compound with a specific rotation of +61.1°. A solution of carvone stereoisomers has an observed specific rotation of 25.0°. Could someone help me Calculate the percent enantiomeric excess (%ee) of this mixture? I tried it but I keep getting the wrong answer.Atorvastatin (Lipitor) is used to decrease patient serum cholesterol levels. It works by inhibiting an enzyme called HMG-COA reductase. See"Connections to Biological Chemistry" one synthesis of atorvastatin that produces the desired single enantiomer of the final product, the following reagents are used. Draw the structures of synthetic intermedi- ates A and B. In -Cl NaCN НО. A B DMSO Pyridine