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answer question 8.14! it is above chart 8.8. use chart 8.8 and chart 8.9 to answer the question! this is complete! there is no missing data here no matter what you think! answer the question!

answer question 8.14! it is above chart 8.8. use chart 8.8 and chart 8.9 to answer the question! this is complete! there is no missing data here no matter what you think! answer the question!

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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answer question 8.14! it is above chart 8.8. use chart 8.8 and chart 8.9 to answer the question! this is complete! there is no missing data here no matter what you think! answer the question!

PROBLEM 8.14 Explain why the carbocation shown in Figure 8.8 has a longer lifetime than it does un- der the conditions shown in Figure 8.9. Ph Ph Ph Сс-он + но-с H + H,O*Cr H. H.C H,C CH, (S-1-Chloro-1-phenylethane (S)-1-Phenylethanol (R)-1-Phenylethanol 50% 50% Hö: Hö: Hö: e Ph Ph Ph HO H HO H. HC H H.C CH, 0 The carbocation formed in this SNI reaction is 2 When water acts as a nucleophile, the initial sp? hybridized and planar. It is not chiral, so the products formed from it must be racemic. The nucleophile-water in this case-can approach equally well from either side, resulting in the formation of equal amounts of the R and S product is the conjugate acid of the alcohol. 3 In the final step of the reaction, a proton is removed from the protonated alcohol by a base in the solution. This base is often a e of the solvent, water in this case. e 316 D molecule enantiomers of the product. Note that it is water, not hydroxide ion, that acts as a nucleo- phile because the concentration of hydroxide ion in neutral water is extremely low. Figure 8.8 MECHANISM AND STEREOCHEMISTRY OF THE SI REACTION OF (S)-1-CHLORO-1- PHENYLETHANE IN AQUEOUS SOLUTION.
Transcribed Image Text:PROBLEM 8.14 Explain why the carbocation shown in Figure 8.8 has a longer lifetime than it does un- der the conditions shown in Figure 8.9. Ph Ph Ph Сс-он + но-с H + H,O*Cr H. H.C H,C CH, (S-1-Chloro-1-phenylethane (S)-1-Phenylethanol (R)-1-Phenylethanol 50% 50% Hö: Hö: Hö: e Ph Ph Ph HO H HO H. HC H H.C CH, 0 The carbocation formed in this SNI reaction is 2 When water acts as a nucleophile, the initial sp? hybridized and planar. It is not chiral, so the products formed from it must be racemic. The nucleophile-water in this case-can approach equally well from either side, resulting in the formation of equal amounts of the R and S product is the conjugate acid of the alcohol. 3 In the final step of the reaction, a proton is removed from the protonated alcohol by a base in the solution. This base is often a e of the solvent, water in this case. e 316 D molecule enantiomers of the product. Note that it is water, not hydroxide ion, that acts as a nucleo- phile because the concentration of hydroxide ion in neutral water is extremely low. Figure 8.8 MECHANISM AND STEREOCHEMISTRY OF THE SI REACTION OF (S)-1-CHLORO-1- PHENYLETHANE IN AQUEOUS SOLUTION.
Ph Ph Ph CH;CO2 Ci: CH;CO OCCH3 H CH;CO,H H H. CH; H;C H3C (S)-1-Chloro-1-phenylethane 58% (R) 42% (S) 16% 42% 42% Ph Ph 84% CH C-O: Ci: Acetate H3C H H3C H CH;C-0: :0-CCH, ion lon pair Free carbocation 3 For the other 84% of the lon pairs, the chloride lon diffuses away before the nucleophile attacks. 1 The Initial species formed in this SNI reaction, a carbocation with the chloride anion situated directly adjacent, Is called an lon pair. There is a competition between reaction of the nucleophile with the lon pair and diffusion of the anlon away 4 The nucleophile can approach the resulting free carbocation equally well from eicher side, result- Ing In the formation of equal amounts of product with retained and Inverted configuration (42% of each). The final result is 42% retention and 16% +42% = 58% Inversion. The reaction has from the carbocation. 2 Under this particular set of reaction condidons, 16% of the lon pairs react with the nucleophile, acetate lon. Because the chloride is blocking one side of the lon pair, acetate can approach only from the opposite side. Therefore, only the product with inverted configuration is formed when the nucleophile reacts at this stage. occurred with racemization and some excess inversion. Figure 8.9 STEREOCHEMISTRY OF THE SNI REACTION OF (S)-1-CHLORO-1-PHENYLETHANE IN ACETIC ACID CONTAINING POTASSIUM ACETATE.
Transcribed Image Text:Ph Ph Ph CH;CO2 Ci: CH;CO OCCH3 H CH;CO,H H H. CH; H;C H3C (S)-1-Chloro-1-phenylethane 58% (R) 42% (S) 16% 42% 42% Ph Ph 84% CH C-O: Ci: Acetate H3C H H3C H CH;C-0: :0-CCH, ion lon pair Free carbocation 3 For the other 84% of the lon pairs, the chloride lon diffuses away before the nucleophile attacks. 1 The Initial species formed in this SNI reaction, a carbocation with the chloride anion situated directly adjacent, Is called an lon pair. There is a competition between reaction of the nucleophile with the lon pair and diffusion of the anlon away 4 The nucleophile can approach the resulting free carbocation equally well from eicher side, result- Ing In the formation of equal amounts of product with retained and Inverted configuration (42% of each). The final result is 42% retention and 16% +42% = 58% Inversion. The reaction has from the carbocation. 2 Under this particular set of reaction condidons, 16% of the lon pairs react with the nucleophile, acetate lon. Because the chloride is blocking one side of the lon pair, acetate can approach only from the opposite side. Therefore, only the product with inverted configuration is formed when the nucleophile reacts at this stage. occurred with racemization and some excess inversion. Figure 8.9 STEREOCHEMISTRY OF THE SNI REACTION OF (S)-1-CHLORO-1-PHENYLETHANE IN ACETIC ACID CONTAINING POTASSIUM ACETATE.
Expert Solution
Introduction

Carbocation are the electron deficient species. They carry a positive charge on carbon atom. The carbocation can be primary, secondary, tertiary, benzylic and allylic etc. According to their nature, their stability will vary.

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