• PRACTICE PROBLEM 6.6 S 2 reactions that involve substitution at a chirality center can be used to relate theconfiguration of one molecule to another, because we know the SN2 reaction will occurwith inversion.(a) Illustrate how this is true by assigning R,S configurations to the 2-chlorobutaneenantiomers based on the following data. [The configuration of (-)-2-butanol is givenin Section 5.8C.]HO-(+)-2-Chlorobutane(-)-2-ButanolSN2[a]3 = +36.00(Enantiomerically pure)[a] = -13.52(Enantiomerically pure)noin(b) When enantiomerically pure (+)-2-chlorobutane is allowed to react with potassiumiodide in acetone in an SN2 reaction, the 2-iodobutane that is produced has a minusoptical rotation. What is the configuration of (-)-2-iodobutane? Of (+)-2-iodobutane?

When reaction is undergoes though SN2 mechanism the configuration of product is 100% inversion , as…

SN2 reactions that involve substitution at a chirality configuration of one molecule to another, because we know the SN2 reaction will os with inversion. (a) Illustrate how this is true by assigning R,S configurations to the 2-chlorobutane enantiomers based on the following data. [The configuration of (-)-2-butanol is give in Section 5.8C.] HO (+)-2-Chlorobutane (-)-2-Butanol SN2 [a]3 = +36.00 (Enantiomerically pure) [a = -13.52 (Enantiomerically pure) %3D (b) When enantiomerically pure (+)-2-chlorobutane is allowed to react with potassiu iodide in acetone in an SN2 reaction, the 2-iodobutane that is produced has a minus optical rotation. What is the configuration of (-)-2-iodobutane? Of (+)-2-iodobutan

SN2 reactions that involve substitution at a chirality configuration of one molecule to another, because we know the SN2 reaction will os with inversion. (a) Illustrate how this is true by assigning R,S configurations to the 2-chlorobutane enantiomers based on the following data. [The configuration of (-)-2-butanol is give in Section 5.8C.] HO (+)-2-Chlorobutane (-)-2-Butanol SN2 [a]3 = +36.00 (Enantiomerically pure) [a = -13.52 (Enantiomerically pure) %3D (b) When enantiomerically pure (+)-2-chlorobutane is allowed to react with potassiu iodide in acetone in an SN2 reaction, the 2-iodobutane that is produced has a minus optical rotation. What is the configuration of (-)-2-iodobutane? Of (+)-2-iodobutan

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution

Section16.SE: Something Extra

Problem 25VC: The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy...

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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) Whichproduct predominates—the product of inversion or the product of retention of conguration? (c) Suggest an explanation for this phenomenon.
In some nucleophilic substitutions under SN1 conditions, completeracemization does not occur and a small excess of one enantiomer ispresent. 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.
6.2 (-)-Cameroonanol has been isolated from the essential oil of Echinops giganteus (globe thistle) plants and it is associated with a strong woody fragrance. Its structure, includ- ing relative stereochemistry, was confirmed when it was made in the laboratory according to the sequence shown below.' Recall that a C=C bond is made up of one o bond and one 7 bond. These two bonds together have a combined BDE (bond dissociation energy) of 607 kJ/mol. Use this information to estimate the AH° for the conversion of compound 1 into compound 2. Br two steps H.. H HBr hv H (-Cameroonanol
Starting with (S)-2-bromobutane, outline syntheses of each of the following compounds:• PRACTICE PROBLEM 6.19 (a) (R)-CH,CHCH,CH3 (c) (R)-CH,CHCH,CH3 OH bA-(2) ÓCH,CH3 SH muinolue for (b) (R)-CH,CHCH,CH3 (d) (R)-CH,CHCH,CH3 tho betallgo ÓCCH3 ŚCH3
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.
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-phenyl-1-propanol. (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. H Br он H20 1-bromo-1-phenylpropane 1-phenyl-1-propanol observed [a) = +5.0 optically pure S isomer, [a] =-48 %3D
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(R)-2-methylbutan -1- ol (structure shown on the right )is an optically active compound that has a specific rotation value of +5.75° over a sodium D-line wavelength at 20°C. It's racemate (same compound different configuration) (S)-2-methylbutan -1- ol would have the same specific rotation value but of opposite sign. a. What are concentrations of both of these compounds if the pathlength used for the cuvette is 2.3 cm and each would have observed rotation of ± 1.151°? b. To arrive at these two compounds as products, what specific molecule should be your starting reactant? Draw a detailed reaction mechanism outline for the formation of these two compounds. Hill H₂C OH CH₂ (R)-2-methylbutan-1-ol
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