Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 6.16, Problem 6.28P
Interpretation Introduction
Interpretation: The enantiomeric excess and expected specific rotation for the expected product is to be calculated on the basis of 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 enantiomeric excess and expected specific rotation for the expected product on the basis of given information.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Assume that (2S,3R)-2-bromo-3-chloropentane
has a specific rotation of +58°. What would be
the specific rotation of the (2R,3S) isomer?
Draw all stereoisomers of 3,4-hexanediamine. Label each sterocenter with the appropriate R/S designation to show hardness. Indicate the relationship(enantiomers or diasteromers) between every possible pairing of compounds. Label each compound as chiral or achiral, and if there is a mess compound, label it as such.one of these compound has a specific rotation of +6.9 degrees. Which compound might this be? What do you expect the specific rotation of the remaining compound to be?
In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1-phenylpropan-1-ol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Which product predominates—the product of inversion or the product of retention of configuration? (c) Suggest an explanation for this phenomenon.
Chapter 6 Solutions
Organic Chemistry (9th Edition)
Ch. 6.1 - Classify each compound as an alkyl halide, a vinyl...Ch. 6.2 - Give the structures of the following compounds. a....Ch. 6.2 - For each of the following compounds, A. give the...Ch. 6.3E - Prob. 6.4PCh. 6.4 - Prob. 6.5PCh. 6.5A - For each pair of compounds, predict which compound...Ch. 6.5B - Prob. 6.7PCh. 6.6B - Prob. 6.8PCh. 6.6B - The light-initiated reaction of...Ch. 6.6B - Show how free-radical halogenation might be used...
Ch. 6.7 - Prob. 6.11PCh. 6.7 - Prob. 6.12PCh. 6.8 - Prob. 6.13PCh. 6.9 - Predict the major products of the following...Ch. 6.9 - Prob. 6.15PCh. 6.10A - Prob. 6.16PCh. 6.11A - When diethyl ether (CH3CH2OCH2CH3) is treated with...Ch. 6.11B - Prob. 6.18PCh. 6.11B - For each pair of compounds, state which compound...Ch. 6.12 - Prob. 6.20PCh. 6.12 - Under appropriate conditions...Ch. 6.13 - Propose an SN1 mechanism for the solvolysis of...Ch. 6.13B - Prob. 6.23PCh. 6.13B - 3-Bromocyclohexene is a secondary halide, and...Ch. 6.15 - Prob. 6.25PCh. 6.15 - Prob. 6.26PCh. 6.16 - For each reaction, give the expected substitution...Ch. 6.16 - Prob. 6.28PCh. 6.16 - Prob. 6.29PCh. 6 - Prob. 6.30SPCh. 6 - Draw the structures of the following compounds. a....Ch. 6 - Give systematic (IUPAC) names for the following...Ch. 6 - Prob. 6.33SPCh. 6 - Predict the compound in each pair that will...Ch. 6 - Prob. 6.35SPCh. 6 - Give two syntheses for (CH3)2CHOCH2CH3, and...Ch. 6 - Prob. 6.37SPCh. 6 - Prob. 6.38SPCh. 6 - Chlorocyclohexane reacts with sodium cyanide...Ch. 6 - Give the substitution products expected from...Ch. 6 - Prob. 6.41SPCh. 6 - Prob. 6.42SPCh. 6 - Two of the carbocations in Problem6-42 are prone...Ch. 6 - Prob. 6.44SPCh. 6 - Predict the products of the following SN2...Ch. 6 - Prob. 6.46SPCh. 6 - Strawberry growers have used large quantities of...Ch. 6 - A solution of pure (S)-2-iodobutane ([]=+15.90) in...Ch. 6 - Prob. 6.49SPCh. 6 - Give a mechanism to explain the two products...Ch. 6 - Prob. 6.51SPCh. 6 - Because the SN1 reaction goes through a flat...Ch. 6 - Prob. 6.53SPCh. 6 - Furfuryl chloride can undergo substitution by both...Ch. 6 - Prob. 6.55SPCh. 6 - The following reaction takes place under...Ch. 6 - Propose mechanisms to account for the observed...Ch. 6 - Prob. 6.58SPCh. 6 - Prob. 6.59SP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- After an attempt to resolve a racemate into its entantiomers, the observed rotation is +22.4 degrees per g/L. If the known specific rotation is +24.2 degrees per g/L, what is the % enantiomeric excess of the compund?arrow_forwardThe specific rotation of (S) butanol is +13.5 if 1.00g of its enantiomer is dissolved in 10.0mL of ethanol and placed in a sample cell with a length of 1.00 dm, what observed rotation do you expect?arrow_forwardThis is an example of a [1,3] sigmatropic rearrangement. Can someone explain how this is 1,3 (number the carbons) and draw the anion / cation transition statearrow_forward
- The specific rotation of (R)-2-chlorobutane is -9.0 degrees. If 2.92 g of its enantiomer is dissolved in 6 mL of ether and placed in a sample cell with a length of 1.0 dm, what observed rotation do you expect (write answer with two decimal places)?arrow_forwardFill in the missing reagents or major products to complete the transformations. Be sure to pay carefulattention to stereochemistry where appropriate. If the major product is a pair of enantiomer you mayshow one of them and indicate + enantiomer. If the products are diasteromers, show them both.arrow_forwardWhat is the product (include the stereochemistry) of the 6 pi electron electrocyclic reaction below, use the appropriate Woodward-Hoffman rule.arrow_forward
- (1) Draw or illustrate the stereochemistry of the product between 1-Ethyl-1-cyclopentene and Br2 and (2) illustrate the reaction mechanism.arrow_forwardwhich newman projection displays the proper antiperiplanar orientation for an E2 elimination of the reaction sequence belowarrow_forwardIn some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer ispresent. For example, treatment of optically pure 1-bromo-1phenylpropane with water forms 1-phenylpropan-1-ol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Which product predominates—the product of inversion or the product of retention of configuration? (c) Suggest an explanation for this phenomenon.arrow_forward
- Compounds with a d10 configuration will not undergo a reductive elimination reaction, why?arrow_forwardConsider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with sodium methoxide. Deduce the mechanism of this reaction working step by step. Write all possible products showing the stereochemistry.arrow_forwardWrite the products of the reaction below and indicate if the product is R or S or racemic or achiral.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning