Question 5 of 50 -/1 > View Policies Current Attempt in Progress When (S)-2-bromopropanoic acid [(S)-CH3CHBPCO,H] reacts with concentrated sodium hydroxide, the product formed (after acidification) is (R)-2-hydroxypropanoic acid [(R)-CH3CHOHCO2H, commonly known as (R)-lactic acid). This is, of course, the normal stereochemical result for an SN2 reaction. However, when the same reaction is carried out with a low concentration of hydroxide ion in the presence of Ag,0 (where Ag* acts as a Lewis acid), it takes place with overall retention of configuration to produce (S)-2- hydroxypropanoic acid. The mechanism of this reaction involves a phenomenon called neighboring-group participation. Explain why there is a net retention of configuration when Ag* and a low concentration of hydroxide are used. The reaction is a two step process. The missing product produced by step 1 is: (Use single up and single down wedges to show the stereochemistry at the chiral center.) Step I HI Br Ag+

Question 5 of 50 -/1 > View Policies Current Attempt in Progress When (S)-2-bromopropanoic acid [(S)-CH3CHBPCO,H] reacts with concentrated sodium hydroxide, the product formed (after acidification) is (R)-2-hydroxypropanoic acid [(R)-CH3CHOHCO2H, commonly known as (R)-lactic acid). This is, of course, the normal stereochemical result for an SN2 reaction. However, when the same reaction is carried out with a low concentration of hydroxide ion in the presence of Ag,0 (where Ag* acts as a Lewis acid), it takes place with overall retention of configuration to produce (S)-2- hydroxypropanoic acid. The mechanism of this reaction involves a phenomenon called neighboring-group participation. Explain why there is a net retention of configuration when Ag* and a low concentration of hydroxide are used. The reaction is a two step process. The missing product produced by step 1 is: (Use single up and single down wedges to show the stereochemistry at the chiral center.) Step I HI Br Ag+

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.58P

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