Question

Page 1 Synthesis using Carbonyl O-Substitution Chemistry Preamble This experiment involves the synthesis of target molecules using a-substitution chemistry. You are assigned two target molecules, one of which is best synthesized by an alkylation approach, while the other is best synthesized by an addition or condensation approach. You must do the following: 1. Perform a retrosynthetic analysis on the two target molecules assigned to you. In each case the organic starting material (what you have to work backwards toward) depends upon the target. For targets 1-10, the starting material is either malonic ester or acetoacetic ester and any halide. For targets 11-16, the starting material is any four carbon halide. Draw a retrosynthetic scheme; use the rightwards double arrow to show functional group transformations and disconnections. 2. Propose the forward synthesis (based upon the retrosynthetic analysis) for each molecule. Include important reagents over the reaction arrows. 3. Provide a paragraph where you explain how each of the chemical reactions required for ONE of the two syntheses will be carried out. The conditions for each step and anticipated purification procedures must be included. You will write up a short paper (no more than 400 words) including 1) the two retrosynthetic and synthetic schemes and 2) A short paragraph outlining the conditions for each step. (One short paragraph per step). The example below is for a similar exercise. Note that the aldol/Claisen target is based on five-carbon alkyl bromides rather than the 4-C starting materials that are specified in your assignment.

Answer 1

The answer is explained in the images.
Given com compound- Retrosynther's scheme FGT CH₃ Br COOH £{ cqe Etol cou U H X +24 CORET forward scheme :- Etzole copet Ctona soge mamy biethylmalonate Lor Etoze (step - Nao Et he-8x (slep- H3 ot/A CO2H stupm) 490 60267 be In step I :- The starting material treated first with sodium ethoxide solution and stirred for some time. Then the 2-bromopropane will be added into it. This step the product extracted postos- by organic sowent like ether. The purification may done by distillation process. In step-u The product from step of treated sodium ethoxide and then methyl will be added. Then product will be extracted from water and ether mixtione. Product will Purification process with Boronide in ether layer. distillation.

and then In third step: - The product from step at will be taken in a Round bottom flask dil Ha solution will be added. and then refluxed. The aced product in extracted by a basic solution and washed with organie solvent (CHUzYet₂0). to unreacted material. Then the extracted solution will be acidified and the product is soluble in organic solvents. Purification : Not needed remove Column chromatography. ЕО I FGI .me FGT OH FGI Br Forward! Me CH₂ cooNa [0] OH pec Et3N is used which gives the product. Note : In the final step weak base Etz thermodynamic enolate which provides