Answered: 16. What is the % ee of a sample of…

16. What is the % ee of a sample of carvone that exhibits a specific rotation of -20, given that the specific rotation of (R)-carvone is -61?

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter5: Alkenes: Bonding, Nomenclature, And Properties

Section: Chapter Questions

Problem 5.36P

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Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

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16. What is the % ee of a sample of carvone that exhibits a specific rotation of -20, given that
the specific rotation of (R)-carvone is -61?

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The specific Rotation of (R)-carvone (at 20 deg) is -61. A chemist prepare a mixture of (r)-carvone and its enantiomer and the mixture has a specific rotation of -55. Calculate the %ee of this mixture. O a. 90% O b.5% O c. 45% O d. 10%
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?
What would the specific rotation of pure (S) carvone be considering R carvone has a specific rotation of -60?
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?
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?
2. Label any stereocenters in the following molecule as (R) or (S): ОН H. .CH3 `CH3 ОН
The specific rotation of optically pure adrenaline in water at 25°C is -53. If a chemist has a sample of synthetic adrenaline with a specific rotation of -45, calculate the enantiomeric excess.
Explain the result of the specific rotation (-130\deg) shown by that compound (C13H1002) based on its molecular structure visualized in three dimensions.
3. The specific rotation of (S)-carvone is +61°. A chemist prepared a mixture of (R)-carvone and its enantiomer, and this mixture had an observed rotation of -50°. A. What is the specific optical rotation of pure (R)-carvone? B. Calculate the %ee of this mixture. C. What percentage of this mixture is (S)-carvone?
If the sample of the pure R enantiomer of a molecule has a specific rotation of -40 degrees and your mixture of that molecule has an 82% ee S, what is the observed specific rotation of your sample?
8. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) H3C c) CH3 Br H. CH3 Br Br CH3 H. CI Holl H Cill Cl- CH3 Br H. CI CH3 HO. H. H3C Cl H3C- H- H. CH3 Cl a) b) c) 9. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) c) CH2CH3 NH2 HO CH3 H3C. CH3 Cl HO H;C CH2CH3 F. F H;C. CI H H,N -CH3 CH3 NH2 H3C Br H2N C1 H3C CH3 CH3 H;CH,C- Cl F H. H Br CH,CH3 CH3 a) b) c)
A certain compound has a specific rotation of -43.2o (c = 5, toluene). What is the observed rotation of a sample of 1.24 g of the enantiomer of this compound when diluted to a concentration of 1.00 g ml-1 in the same solvent? Example 30 In his classic studies of stereochemistry and optical activity in organic compounds, Pasteur measured the optical activity of many solutions. For the naturally occurring enantiomer of tartaric acid, [α]D20 = +12.4o (c = 20, H2O). What can be concluded about the ratio of tartaric acid enantiomers present in the solution if the observed rotation is (i) α = -6.0o, or (ii) α = 0o?