Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 3, Problem 3.29P
Interpretation Introduction
Interpretation:
For the given compound, the actual rotation is not really +40 plus some multiple of +360 this has to be explained.
Concept Introduction:
Stereoisomers and chiral:
Isomers differing only in their spatial arrangement of atoms are called as stereoisomers.
The geometric property of a molecule that cannot be superimposed on its mirror image is known as chirality. Chiral carbon is the one which is attached with four different groups or atoms.
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Chapter 3 Solutions
Organic Chemistry
Ch. 3.2 - Prob. 3.1PCh. 3.3 - Assign priorities to the groups in each set. (a)...Ch. 3.3 - Prob. 3.3PCh. 3.4 - Following are stereorepresentations for the four...Ch. 3.4 - Prob. 3.5PCh. 3.4 - Prob. 3.6PCh. 3.5 - How many stereoisomers exist for...Ch. 3.5 - How many stereoisomers exist for...Ch. 3.7 - Prob. 3.9PCh. 3.7 - Prob. 3.10P
Ch. 3.8 - If the side chain of the amino add is a methyl...Ch. 3.8 - Prob. BQCh. 3.8 - The amino acids cysteine and serine are shown....Ch. 3.8 - Prob. DQCh. 3.8 - As stated, proteins are stereochemically pure...Ch. 3.8 - As stated, proteins are stereochemically pure...Ch. 3 - Prob. 3.11PCh. 3 - One reason we can be sure that sp3-hybridized...Ch. 3 - Which compounds contain chiral centers? (a)...Ch. 3 - Prob. 3.15PCh. 3 - Prob. 3.16PCh. 3 - Prob. 3.17PCh. 3 - Mark each chiral center in the following molecules...Ch. 3 - Prob. 3.19PCh. 3 - Assign priorities to the groups in each set. (a) H...Ch. 3 - Following are structural formulas for the...Ch. 3 - Following is a staggered conformation for one of...Ch. 3 - Prob. 3.23PCh. 3 - When oxaloacetic acid and acetyl-coenzyme A...Ch. 3 - Prob. 3.25PCh. 3 - Mark each chiral center in the following molecules...Ch. 3 - Prob. 3.27PCh. 3 - Prob. 3.28PCh. 3 - Prob. 3.29PCh. 3 - Prob. 3.30PCh. 3 - Which of the following are meso compounds?Ch. 3 - Prob. 3.32PCh. 3 - Prob. 3.33PCh. 3 - Which of the following compounds are chiral?...Ch. 3 - Prob. 3.35PCh. 3 - Prob. 3.36PCh. 3 - Prob. 3.37PCh. 3 - The chiral catalyst (R)-BINAP-Ru is used to...Ch. 3 - Prob. 3.39P
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- 1. When 0.247 g of monosodium glutamate (MSG) is dissolved in 10.0 mL of water and placed in a sample cell 10.0 cm in length, the observed rotation at 20°(using the D line of sodium) is +0.632°. Calculate the specific rotation of MSG. 2. When 0.095 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°C (using the D line of sodium) is -0.299°.Calculate the specific rotation of cholesterol.3. The specific rotation of L-dopa in water (at 15°C) is -39.5. A chemist prepared a mixture of L-dopa and its enantiomer, and this mixture had a specific rotation of -34. Calculate the % ee of this mixture. 4. 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_forwardIf a substance is known to have a specific rotation of -89.3 deg mL/g dm, what is the concentration (in g/mL) of a solution that would give an observed rotation of -25.5 degrees, if the path length of the sample tube was 2.00 dm? (Hint: Rearrange the specific rotation calculation formula)arrow_forwardIf a substance is known to have a specific rotation of +20.0 deg mL/g dm, what is the concentration (in g/mL) of a solution that would give an observed rotation of +10.0 degrees, if the path length of the sample tube was 1.00 dm? Can you do this problem in your head?arrow_forward
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- The 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_forwardCalculate the specific rotation of 120mL methyl salicylate (C8H8O3) if the molar rotation is -1.50°. (MW= 152)arrow_forwardIf 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?arrow_forward
- 13. You are given the following data for the stereoisomer shown. You have a sample of this molecule that has a measured optical rotation identical to this data. Which of the following statements do you know are TRUE? Br [a] = -23.1 O A. A sample with an optical rotation of -13.1 has an enantiomeric excess of the S isomer. O B. A sample with a 75% of the S sample and a 25% of the R samplearrow_forwardWhen 0.075g of penicillamine is dissolved in 10.0 mL of pyridine and placed in a sample cell 10.0 cm in length, the observed rotation at 20 degrees (using the D line of sodium) is -0.47 degrees. Calculate the specific rotation of penicillamine. a. (-0.47)/[(0.075g/mL) (1.00 dm)]= -6.3 b. (0.47)/[(0.075g/mL) (1.00 dm)]= 6.3 c. (-0.47)/[(0.0075g/mL) (1.00 dm)]= -63 d. (0.47)/[(0.0075g/mL) (1.00 dm)]= 63arrow_forward(S)-2-Bromobutane has a specific rotation of +23.1°. Suppose that a solution is made by dissolving 20.00 g of (S)-2-bromobutane in 1.00 L total solution. What would be the measured rotation of plane-polarized light sent througha 10.00-cm tube containing that solution?arrow_forward
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