When (S)-2-bromopropanoic acid [(S)-CH;CHBFCO,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 SN2reaction. However, when the same reaction is carried out with a low concentration of hydroxide ion in the presence of Ag20 (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 H Br CH;
Carbohydrates
Carbohydrates are the organic compounds that are obtained in foods and living matters in the shape of sugars, cellulose, and starch. The general formula of carbohydrates is Cn(H2O)2. The ratio of H and O present in carbohydrates is identical to water.
Starch
Starch is a polysaccharide carbohydrate that belongs to the category of polysaccharide carbohydrates.
Mutarotation
The rotation of a particular structure of the chiral compound because of the epimerization is called mutarotation. It is the repercussion of the ring chain tautomerism. In terms of glucose, this can be defined as the modification in the equilibrium of the α- and β- glucose anomers upon its dissolution in the solvent water. This process is usually seen in the chemistry of carbohydrates.
L Sugar
A chemical compound that is represented with a molecular formula C6H12O6 is called L-(-) sugar. At the carbon’s 5th position, the hydroxyl group is placed to the compound’s left and therefore the sugar is represented as L(-)-sugar. It is capable of rotating the polarized light’s plane in the direction anticlockwise. L isomers are one of the 2 isomers formed by the configurational stereochemistry of the carbohydrates.
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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
Ag+
H Br
CH,](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fdfeb6ece-b69f-4bf1-a198-9823766b6f38%2Fa758f265-6991-4f29-a090-09803d6bacf9%2Futujnhm_processed.png&w=3840&q=75)
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