Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 4.9, Problem 22P
(S)-(+)-Monosodium glutamate (MSG) is a flavor enhancer used in many foods. Some people have an allergic reaction to MSG (including headache, chest pain, and an overall feeling of weakness), fast food often contains substantial amounts of MSG. which is widely used in Chinese food as well (S)-(+)-MSG has a specific rotation of +24.
- a. What is the specific rotation of (R)-(–)-monosodium glutamate?
- b. What is the specific rotation of a racemic mixture of MSG?
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(S)-(+)-Monosodium glutamate (MSG) is a flavor enhancer used in many foods. Some people have an allergic reaction to MSG (including headache, chest pain, and an overall feeling of weakness). Fast food often contains substantial amounts of MSG, which is widely used in Chinese food as well. (S)-(+)-MSG has a specific rotation of +24.a. What is the specific rotation of (R)-(-)-monosodium glutamate? b. What is the specific rotation of a racemic mixture of MSG?
(S)-(+)-Monosodium glutamate (MSG) is a flavor enhancer used in many foods. Some people have an allergic reaction to MSG (including headache, chest pain, and an overall feeling of weakness). "Fast food" often contains substantial amounts of MSG, which is widely used in Chinese food as well. (S)-(+)-MSG has a specific rotation of +24.
a). What is the specific rotation of (R)-(−)-monosodium glutamate?
b). What is the specific rotation of a racemic mixture of MSG?
The specific rotation of quinine, an anti-malarial drug, is -165°. How much quinine (in %) is present in a sample that
has an observed specific rotation of 33°?
CH3O
HO
H
H
quinine
(antimalarial drug)
Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Prob. 2PCh. 4.1 - Prob. 3PCh. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.1 - Which of the roll owing compounds have a dipole...Ch. 4.2 - Prob. 7PCh. 4.3 - Prob. 8PCh. 4.4 - Prob. 10PCh. 4.4 - Prob. 11PCh. 4.6 - Prob. 12P
Ch. 4.7 - Prob. 14PCh. 4.7 - Prob. 16PCh. 4.7 - Prob. 17PCh. 4.7 - Draw a perspective formula for each or the...Ch. 4.8 - Prob. 20PCh. 4.9 - Prob. 21PCh. 4.9 - (S)-(+)-Monosodium glutamate (MSG) is a flavor...Ch. 4.10 - Prob. 23PCh. 4.10 - Prob. 24PCh. 4.11 - Prob. 26PCh. 4.11 - Prob. 27PCh. 4.11 - Prob. 28PCh. 4.11 - The stereoisomer of cholesterol found in nature is...Ch. 4.11 - Prob. 30PCh. 4.12 - Prob. 31PCh. 4.12 - Draw all possible stereoisomers for each of the...Ch. 4.12 - Prob. 33PCh. 4.12 - Of all the possible cyclooctanes that have one...Ch. 4.12 - Prob. 35PCh. 4.12 - Prob. 36PCh. 4.13 - Which of the following compounds has a...Ch. 4.13 - Prob. 39PCh. 4.14 - Prob. 40PCh. 4.14 - Name the isomers you drew in Problem 52.Ch. 4.14 - Chloramphenicol is a broad-spectrum antibiotic...Ch. 4.14 - Draw a perspective formula for each of the...Ch. 4.14 - Name the following:Ch. 4.14 - Prob. 45PCh. 4.14 - Prob. 48PCh. 4.14 - Prob. 50PCh. 4.15 - Limonene exists as two different stereoisomers....Ch. 4.16 - Prob. 52PCh. 4 - a. Draw three constitutional isomers with...Ch. 4 - Prob. 53PCh. 4 - Prob. 54PCh. 4 - Which of the following has an asymmetric center?...Ch. 4 - Prob. 56PCh. 4 - Prob. 57PCh. 4 - Prob. 58PCh. 4 - Which of the following are optically active?Ch. 4 - Prob. 60PCh. 4 - Prob. 61PCh. 4 - Which of the following has an achiral...Ch. 4 - Prob. 63PCh. 4 - Prob. 64PCh. 4 - Prob. 65PCh. 4 - Prob. 66PCh. 4 - Prob. 67PCh. 4 - Prob. 68PCh. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Prob. 71PCh. 4 - Prob. 72PCh. 4 - Prob. 73PCh. 4 - a. Draw all the isomers with molecular formula...Ch. 4 - Prob. 75PCh. 4 - Prob. 76PCh. 4 - Draw structures for the following: a....Ch. 4 - Prob. 78PCh. 4 - Prob. 79PCh. 4 - Prob. 80PCh. 4 - a. Using the wedge-and-dash notation, draw the...Ch. 4 - Prob. 82PCh. 4 - Prob. 83PCh. 4 - Prob. 84PCh. 4 - a. Draw the two chair conformers for each of the...Ch. 4 - Prob. 86PCh. 4 - Is the following compound optically active?
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- The specific rotation of the pure (S) form of Ivermectin is +85.0° when measured using light with a 500 nm wavelength. Ivermectin is an expensive component of a popular COVID treatment called NO-FX. To save money, the Trumpharm company makes NO-FX by mixing inexpensive racemic Ivermectin with some enantiomerically pure Ivermectin. A 1.3 g sample of NO-FX is dissolved in 6.0 mL of CHCl3. When placed in a 1 cm cell, the observed rotation at 500 nm is -0.6°. a) What is the specific rotation of the sample? b) Which isomer is in excess and how do you know it is in excess? c) What is the optical purity of the sample?arrow_forwardThe specific rotation of vitamin C ( using the D line of sodium, at 20°C) is +24. Predict what the observed rotation would be for a solution containing 0.100 g of vitamin C dissolved in 10.0 ml of ethanol and placed in a sample cell with a length of 1dm.arrow_forwardIf (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_forward
- The specific rotation of vitamin B7 in water (22°C) is +92°. A mixture of vitamin B7 and its enantiomer has a specific rotation of + 27.6°. What is the percentage of vitamin B7 and its enantiomer in this mixture? Select one: O A. 60% vitamin B7 : 40% enantiomer B. 65% vitamin B7 : 35% enantiomer C. 55% vitamin B7 : 45% enantiomer D. 70% vitamin B7 : 30% enantiomerarrow_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_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
- The specific rotation of vitamin B7 in water (at 22°C) is +92. A chemist prepared a mixture of vitamin B7 and its enantiomer, and this mixture had a specific rotation of +18. Calculate the % ee of this mixture.arrow_forwardThe specific rotation of S-Ibuprofen is +54.5o. Which direction would a mixture containing 80% S-Ibuprofen and 10% R-ibuprofen rotate plane polarized light? To the left or to the right?arrow_forwardConsider a solution that contains 74.0% R isomer and 26.0% S isomer. If the observed specific rotation of the mixture is -45.0°, what is the specific rotation of the pure R isomer? [a] =arrow_forward
- Pure cholesterol has a specific rotation of −32. A sample of cholesterolprepared in the lab had a specific rotation of −16. What is the enantiomericexcess of this sample of cholesterol?arrow_forward6. Sucrose is one of the most abundant sugar in the world. About 185 million tonnes of sugar were produced worldwide in 2017. Sucrose is a chiral compound and enantio-pure sucrose has specific rotation [a]30 = +66.5°. CH,OH CH2OH он OH CH2OH OH OH (+)-Sucrose A sample of synthesized sucrose from organic chemistry lab was tested, and the specific rotation of the sample is [a]0 = +60.1°. a) determine the enantiomeric excess (ee) of the sample. b) calculate the ratio of two enantiomers c) draw the structure of the minor enantiomer in the sample.arrow_forward#23arrow_forward
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