2. The malonic ester synthesis is used to make amino acids. Compound A is the starting material to make amino acid B. NH

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2 The Malonic Ester Synthesis Is Used To Make Amino Acids Compound A Is The Starting Material To Make Amino Acid B Nh 1 (215.95 KiB) Viewed 47 times

2. The malonic ester synthesis is used to make amino acids. Compound A is the starting material to make amino acid B. NH2 alla HO HN A amino acid B a. Step 1: acid-base reaction. (i) Draw in the H on the alpha C in Compound A. (ii) State the pk, of this acid. (iii) Would you use H20, NaOC2H5, or N(C3H7)2 to remove this proton? Give reasons. (iv) Draw the structure of the enolate ion. Step 1 Step 2 Step 3 Step 4 wobei NH2 enolate ion НО C D HN base R-X heat H 0+ “Η А. H - CO2 amino acid B b. Step 2: alkylate the alpha carbon. (i) Draw the structure of the alkyl halide RX that reacts with your enolate ion in Step 1 that forms amino acid B. (ii) Use curved arrows to show how this reaction occurs. Draw the structure of Compound C. (iii) The enolate ion can react with your RX in an unwanted side reaction to form a compound that lowers the yield of Compound C. Draw the structure of the compound that forms in this unwanted side reaction. c. Step 3: Convert ester to acid using H30*. A 3'd group in Compound C reacts with H30*. (i) Circle this group in Compound C. (ii) Use curved arrows to show how this group reacts with H30* to form an intermediate and how this intermediate reacts with water to form a tetrahedral intermediate. Circle the group in your tetrahedral intermediate that behaves like a leaving group. (iii) Draw Compound D. d. Step 4: decarboxylation to form amino acid B. Circle the bond in Compound D that breaks to form CO2 and amino acid B. e. Compound A has an amide group. This group is converted to an amine group to make amino acid B. If Compound A used an amine group instead of an amide group, the yield of amino acid B would be lower because the amine group reacts in Step - with