Organic Chemistry, Books a la Carte Edition (9th Edition)
9th Edition
ISBN: 9780134160382
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 5.4D, Problem 5.10P
Interpretation Introduction
Interpretation: The method to determine the sign of rotation of the given sample is to be stated on the basis of the given information.
Concept introduction: The concentration of the compound affects the rotation of polarized light in Polarimeter. The rotation is also dependent upon the length of the cell and optical activity of the compound. Optical purity of a compound is measured by the enantiomeric excess.
To determine: The sign of rotation of the given sample on the basis of given information.
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Chapter 5 Solutions
Organic Chemistry, Books a la Carte Edition (9th Edition)
Ch. 5.2 - Determine whether the following objects are chiral...Ch. 5.2A - Prob. 5.2PCh. 5.2B - Prob. 5.3PCh. 5.2B - Prob. 5.4PCh. 5.2C - Prob. 5.5PCh. 5.3 - Prob. 5.6PCh. 5.3 - Prob. 5.7PCh. 5.4D - Prob. 5.8PCh. 5.4D - Prob. 5.9PCh. 5.4D - Prob. 5.10P
Ch. 5.5 - Prob. 5.11PCh. 5.7 - When optically pure (R)-2-bromobutane is heated...Ch. 5.7 - Prob. 5.13PCh. 5.8 - Prob. 5.14PCh. 5.9B - Draw three-dimensional representations of the...Ch. 5.10A - For each sot of examples, make a model of the...Ch. 5.10A - Draw a Fischer projection for each compound....Ch. 5.10B - Prob. 5.18PCh. 5.10C - For each Fischer projection, label each asymmetric...Ch. 5.11C - Prob. 5.20PCh. 5.13 - Prob. 5.21PCh. 5.13 - Prob. 5.22PCh. 5.15 - Prob. 5.23PCh. 5.16A - Prob. 5.24PCh. 5 - The following four structures are naturally...Ch. 5 - For each structure, 1. star () any asymmetric...Ch. 5 - Prob. 5.27SPCh. 5 - Prob. 5.28SPCh. 5 - Prob. 5.29SPCh. 5 - Prob. 5.30SPCh. 5 - Prob. 5.31SPCh. 5 - Prob. 5.32SPCh. 5 - Prob. 5.33SPCh. 5 - Prob. 5.34SPCh. 5 - For each structure, 1. draw all the stereoisomers....Ch. 5 - Prob. 5.36SPCh. 5 - Prob. 5.37SPCh. 5 - 3,4-Dimethylpent-1-ene has the formula...Ch. 5 - A graduate student was studying enzymatic...Ch. 5 - Prob. 5.40SPCh. 5 - Prob. 5.41SP
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- 2. Consider this compound: 0 a) How many chiral carbons does this compound have" b) What is the maximum number of stereoisomers that could exist for this compound? Show how you arrived at your answer.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_forwardHow can we decide whether an observed rotation of a solution of an optically active compound is +170° and not actually -190°?arrow_forward
- 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_forwardAtorvastatin is sold under the trade name Lipitor and is used for lowering cholesterol. Annual global sales of this compound exceed $13 billion. Assign a configuration to each chiral center in atorvastatin: 12 32 33 18 36 39 42 13 11 OH OH 19 14 9 6 34 37 40 OH 41 15 3 20 35 38 H 1021 16 17 30 22 25 26 29 28 23 24 27 31 In the boxes below, first input the numbers corresponding to the chiral centers in numerical order as a comma separated list (e.g., "1,3,4"). Then input the configurations of the chiral centers in the same order and format (e.g., "R,S,S"). chiral center(s): Configuration(s):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
- 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_forwardSpecify the configurations (R or S) at ALL chiral centers in the molecules below. Please note that some molecules below may have more than 1 chiral centers, and you are responsible to find all the chiral centers.arrow_forwardDraw a chiral molecule with two chiral centers and determine the absolute configuration (R or S) at each chiral center.arrow_forward
- H ÇI CH3-C-COOH он CH3-C-CH2Br 1. ČI a b 81. Consider the structures above. Which of these two contains a stereocenter? Draw thestructure on your answer sheet and mark the stereocenter with an asterisk. 82. Which of these two is a chiral molecule? Explain your answer. 83. Which of these two can exist as a pair of enantiomers? 84. Draw the pair of enantiomers using three-dimensional representation.arrow_forwardWhat type of stereochemistry, S or R, does the chiral center in this molecule have?arrow_forwardIdentify the chiral centers (mark with *) of the molecule below and assign the absolute configuration of the chiral centers.arrow_forward
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