(a)
To drraw: The structure of
Interpretation: The structure of
Concept introduction: The enantiomers of a chiral compound can be named with the help of right hand and left hand configuration. In fisher projection, chiral carbon atom is represented by a cross. When two groups on a fisher projection are interchanged, the configuration of chiral carbon also changes from (R) to (S) or (S) to (R).
(b)
To determine: The specific rotation of
Interpretation: The specific rotation of
Concept introduction: The enantiomers of a chiral compound can be named the help of right hand and left hand configuration. In fisher projection, chiral carbon atom is represented by a cross. When two groups on a fisher projection are interchanged, the configuration of chiral carbon also changes from (R) to (S) or (S) to (R).
(c)
To determine: The percentage composition of a mixture of (R) and
Interpretation: The percentage composition of a mixture of (R) and
Concept introduction: The enantiomers of a chiral compound can be named with the help of right hand and left hand configuration. In fisher projection, chiral carbon atom is represented by a cross. When two groups on a fisher projection are interchanged, the configuration of chiral carbon also changes from (R) to (S) or (S) to (R).
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Chapter 5 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
- 5. The specific rotation of (S)-2-iodobutane is +15.90°. Draw the structure of (S)-2- iodobutane, predict the specific rotation of (R)-2-iodobutane, and determine the percentage composition of a mixture of (R)- and (S)-2-iodobutane with a specific rotation of -7.95°.arrow_forwardA sample mixture containing the made-up enantiomers (R)-(+)-Nenamide and (S)-(-)-Nenamide has an apparent specific rotation of +6.50° at 25 °C. This sample has an enantiomeric excess (EE) of 43.0%. Provide answers to the following questions : 1.Which enantiomer is in excess in the sample? 2.What is the specific rotation of (S)-(-)-Nenamide?arrow_forward13. If the proton-pump inhibitor, (S)-omeprazole, has a specific rotation (rotation of plane polarized light) of -155°, what should the specific rotation of (R)-omeprazole be? a) -155° b) 0° c) +155° d) It can only be determined experimentallyarrow_forward
- (+) Chloramphenicol is a powerful antibiotic isolated in 1949 from the Streptomyces venezuelae bacterium. Its specific rotation is +18.6°. What is the composition of a mixture of (+) and (-) chloramphenicol whose observed specific rotation is +14.88° ? Select one: A. 60% (+) chloramphenicol and 40 % (-) chloramphenicol B. 70% (+) chloramphenicol and 30 % (-) chloramphenicol C. 90% (+) chloramphenicol and 10 % (-) chloramphenicol D. 80% (+) chloramphenicol and 20 % (-) chloramphenicolarrow_forwardWhen 0.018 g of cholesterol is dissolved in 1.00 mL of ether and placed in a sample cell 10.0 cm in length, the observed rotation at 20 degrees (Using the D line of sodium) is -0.0567 degrees. Calculate the specific rotation of cholesterol. specific rotation= [α] =arrow_forwardThe 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.arrow_forward
- The specific rotation (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. What is the specific rotation of (R)-carvone at 20°C?arrow_forwardAnswer 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.arrow_forward7) a) Assign R and S configuration to the chirality centers of molecules 28 and 29. III CH3 H. H3C CH3 28 29 IV b) Draw the structure of the major product 30, resulting from the following reaction. if you measured the optical rotation of product 30, would it be positive, negative or zero. Briefly justify your answer. NaOH CH3 rate = k [28][NaOH] H3C 28 30 [a]D= 45 ° optical rotation of product 30 c) Draw the structure of the major chiral product 31, resulting from the following reaction. H,SO4 Y.... CH3OH "CH3 29 rate = k [29][CH3OH] 31 d) Draw the structure of the major chiral product 32, resulting from the following reaction. 1) CH3MgBr rate = k [29][CH3MgBr] 2) Н,О 32 29arrow_forward
- The specific rotation of (R)-2-chlorobutane is -9.0 degrees. If 2.92 g of its enantiomer is dissolved in 6 mL of ether and placed in a sample cell with a length of 1.0 dm, what observed rotation do you expect (write answer with two decimal places)?arrow_forwardThe specific rotation of (S)-2-iodobutane is +15.90°. Predict the specific rotation of (R)-2-iodobutane.arrow_forward4 What are enantiomers? What instrument can you use to distinguish the enantiomers? What is racemic mixture? What is enantiomeric excess (e.e)? 5 For a chiral compound with 2 chiral centers how many configurations (also called isomers in lose sense) are possible. Use 2¹ rule. 6 Pure (R)- lactic acid has rotation of + 12.31º. A mixture of lactic acid has a specific rotation of +2.71º. Determine the percent composition of two enantiomers (R) and (S) in the mixture.arrow_forward
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