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) The major component of orange oil is limonene which has a specific rotation of +115.5°. Compare this value with the specific rotation you calculated from your own sample. Is your sample pure? Describe a method you might use to determine the composition of your mixture. My specific rotation was +17.425 2) Many organic reactions result in mixtures of enantiomers in equal amounts, a racemic mixture, which results in zero observable rotation. Chemists have developed selective reactions that result in more of one enantiomer than the other (enantiomer excess). If a mixture of R and S enantiomers has an observed rotation is +25° and the S enantiomer has a +45° rotation, calculate the % enantiometric excess and composition of the mixture.arrow_forward1. 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_forwardExplain the relationship between optical activity and specific rotation with examples.arrow_forward
- 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_forwardHow can we decide whether an observed rotation of a solution of an optically active compound is +170° and not actually -190°?arrow_forward2. The observed rotation of a compound, X (14.0g dissolved in water to make 100ml. of solution) in a polarimeter tube of length 30cm is +10.5°. What is the specific rotation of X?arrow_forward
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