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Concept explainers
(a)
Interpretation:
The specific rotation of (R)-(-)-monosodium has to be calculated.
Concept introduction:
The pair of Enantiomers has different configurations.
Pair of enantiomers has different optical activity, which means if one will show levorotatory then the other will show dextrorotatory.
The direction and magnitude of rotation of plane-polarized light by an optically compound is measured by using polarimeter.
This rotation of polarized light is specific for a compound at specified temperature and wavelength, so it is called as Specific rotation of that compound.
The specific rotation of enantiomers has equal magnitudes and opposite signs.
Racemic mixture (equal amounts of enantiomers) of a compound has zero specific rotation.
(b)
Interpretation:
The specific rotation of racemic mixture of monosodium glutamate has to be calculated.
Concept introduction:
The pair of Enantiomers has different configurations.
Pair of enantiomers has different optical activity, which means if one will show levorotatory then the other will show dextrorotatory.
The direction and magnitude of rotation of plane-polarized light by an optically compound is measured by using polarimeter.
This rotation of polarized light is specific for a compound at specified temperature and wavelength, so it is called as Specific rotation of that compound.
The specific rotation of enantiomers has equal magnitudes and opposite signs.
Racemic mixture (equal amounts of enantiomers) of a compound has zero specific rotation.
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Chapter 4 Solutions
Pearson eText for Essential Organic Chemistry -- Instant Access (Pearson+)
- Glutamic acid is a naturally occurring amino acid and isthe precursor to the food additive MSG (monosodium glutamate)which can cause allergic reactions in some people. If naturally occurring L glutamic acid has a melting point of 205 C and an optical rotation of + 31.5, what is the melting point and optical rotation of its enantiomer?arrow_forwardGlutamic acid is a naturally occurring amino acid and is the precursor to the food additive MSG (monosodium glutamate) which can cause allergic reactions in some people. If naturally occurring L glutamic acid has a melting point of 205 C and an optical rotation of + 31.5, what is the melting point and optical rotation of its enantiomer?arrow_forwardThe specific rotation for compound D is -8.5° dm 1(g/mL)-1, what is the specific rotation of compound E under the same conditions? [a] = -8.5° dm-1 (g/mL)-1 OH O он О он ОН D E -8.5° dm-1 (g/mL)-1 +8.5° dm-1 (g/mL)-1 0° dm-1 (g/mL)-1 not enough information is provided to determine a valuearrow_forward
- If (S)-glyceraldehyde has a specific rotation of -8.7 what is the specific rotation of (R)- glyceraldehyde? O A) -8.7° O B) 0.0° OC) +8.7° O D) cannot be determined from the information givenarrow_forwardAns: 2. Assign the absolute configuration of the chirality center as R or S. O HO- Ans: Assign the absolute configuration of the chirality center as R or S. Ans: OH 3. Drawn below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol. Assign the absolute configurations of the two chirality centers as R or S. | NH 4. What is the relationship of the following two structures? OH OHI NH OH OH A. Enantiomers B. Diastereomers. C. Constitutional isomers D. Identical Ans: NH CO₂H 5. What is the relationship of the following two structures? OH OH A. Enantiomers B. Diastereomers C. Constitutional isomers D. Identical Ans: Loo HO OH 6. What is the relationship of the following two structures? HO HO \,.. ...NH محمد HO OH eilte neu-1071 Mamos a diartwollen preto aarrow_forwardNote: enantiomers have similar physical properties (mp, density, solubility), and same [a], but with different signs ( - or +). Practice: 1.2 gm sample of cocaine, [a], = -16º, was dissolved in 7.5 mL of chloroform and placed in a sample tube having a pathlength of 5 cm. what was the observed rotation in degrees?arrow_forward
- 1. Which of the following molecules are chiral? Identify the chirality center(s) in each. (a) -CH3 (b) -CH2CH2CH3 (c) CH3CH2 Toluene Coniine (from poison hemlock) H. Phenobarbital (tranquilizer) 2. A 1.50 g sample of coniine, the toxic extract of poison hemlock, was dissolved in 10.0 mL of ethanol and placed in a sample cell with a 5.00 cm pathlength. The observed rotation at the sodium D line was +1.21°. Calculate [a]p for coniine. 3. Rank the substituents in each of the following sets: (а) -Н, -ОН, -CH-CH3, -СH>СH,ОН (b) -СО-Н, -СО,CH3, -СH2ОH, -он (c) -CN, -CH2NH2, -CH2NHCH3, –NH2 (d) –SH, –CH2SCH3, –CH3, –SSCH3 4. Assign R,S configurations to the following molecules: (a) Br (b) H (c) NH2 H3C-CO2H HOC-CO2H CH3 NCC-CH3 H H 5. Assign R or S configuration to each chirality center in the following molecules: (a) Br (b) CH3 CH3 HaBr (c) HaCH3 BraH H3C" OH H CH3 OH CH3 OH Which of these compounds are enantiomers, and which are diastereomers? 6. Which of the following substances have meso…arrow_forwardLABEL CHIRAL CENTRESa.2,4-dimethyl heptane b. CH3CH2CH2 CH(Cl)CH3 c. CH3C(OH)(H)(COOH) d. CH3CH2CH(CH3)(H)CHC=CH2 e. CH3 CH2C(CH3)2CH2CH3arrow_forwardThe specific rotation for (-)-methylphenidate is -38° mL g¹ dm¯1. Path length of the polarimeter is 1 dm. 1 You dissolve 0.5 g of a mixture of (-)-methylphenidate and its enantiomer in 4 mL of water. You place the sample into a polarimeter and the observed rotation is found to be -0.2°. What percent of the mixture is composed of (-)- methylphenidate? (Round your answer to the nearest whole percent.) The numerical values in this calculation will change with each attempt. Double check before submitting additional attempts. 17arrow_forward
- Molnupiraviris a promising drug candidate that is discovered to treat patients with Covid-19. The drug is more advantageous than Remdesivir because it is administered orally. The structure of Molnupiraviris drawn below: *Figure in the screenshot* a. How many chirality centers exist on this drug? b. How many maximum numbers of stereoisomers with respect to chiral centers exist? c. Determine R/S configuration of each chiral centeronMolnupiravirby pointing to each chiral center with an arrow on the structure above d. Draw the enantiomer of Molnupiraviracross from it above e. MolnupiravirdestroysCorona virus by introducing error during viral RNA replication. If you were a physician, would you administer a pill that consists of a racemic mixture of Molnupiravirand its enantiomer to a covid positive patient? What would be your expectations? Give your reasons.arrow_forwardCoibacin B is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites. Assign the configuration of each chiral center in coibacin B H.arrow_forwardPrectice q #12 The specific rotation of the pure (S) form of effluvium is -25.0°. Efflivium is an expensive component of a popular natural health product called Snake Oil. To save money, the ACME drug company make Snake Oil by mixing inexpensive racemic effluvium with some enantiomerically pure effluvium. The resulting drug gives a specific rotation of+16° a) What is the enantiomeric excess of the sample? b) Which isomer is in excess and why? c) What is the composition of the mixture (how much R form and how much S form)? d) What was the original ratio used of racemic effluvium to enantiomerically pure effluvium?arrow_forward
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
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