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Page 1 Synthesis using Carbonyl O-Substitution Chemistry Preamble This experiment involves the synthesis of target molecules...


Page 1 Synthesis using Carbonyl O-Substitution Chemistry Preamble This experiment involves the synthesis of target molecules
Page 2 My submission for this assignment would look something like this: a-Substitution Synthesis John Doe Retrosynthetic Ana
Page 3 for diethyl malonate is 200°C at atmospheric pressure (Sigma Aldrich), so the expected boiling point of the product wi


Synthesis using Carbonyla-Substitution Chemistry Preamble This experiment involves the synthesis of target molecules using a-
Synthesis using Carbonyla-Substitution Chemistry My submission for this assignment would look something like this: a-Substitu
Synthesis using Carbonyla-Substitution Chemistry for diethyl malonate is 200°C at atmospheric pressure (Sigma Aldrich), so th
Synthesis using Carbonyla-Substitution Chemistry a-substitution TMs Aldo/Claisen TMs Number Structure Number Structure 11 H
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.
Page 2 My submission for this assignment would look something like this: a-Substitution Synthesis John Doe Retrosynthetic Analysis (target 1): сон Ph FGI ROCCOR РЬ СС ROCCOR C-C ROC COR Proposed Synthesis: (1) NOR ROC COR (1) NOR HO ROCCOR X ROCCOR Ph TM H H Δ 2) Ph Br Br - II Retrosynthetic analysis (target 2): OH Br Proposed Synthesis: NOA HO 10] base ar TM Br OH Δ Proposal (Target 1): In the first step, diethyl malonate will be treated with sodium ethoxide in ethanol and 2-bromopropane will be added. After extraction with water and ether to remove any inorganic salts and removal of solvent, the product will be purified by distillation or vacuum distillation. The literature boiling point
Page 3 for diethyl malonate is 200°C at atmospheric pressure (Sigma Aldrich), so the expected boiling point of the product will be slightly higher. In the second step, the same approach will be taken. The product I will be treated with sodium ethoxide in ethanol, followed by benzyl bromide. After washing a solution of the compound to remove inorganic salts and evaporation of solvents, purification by vacuum distillation is likely to be the most appropriate choice for this high molecular-weight compound. In the third step, the product II will be heated under reflux with dilute acid. The carboxylic acid product will be extracted into a basic solution and washed with an organic solvent such as ether in order to remove any unreacted starting material. After acidification, the product (2-benzyl-3- methylbutanoic acid) will become soluble in organic solvents and can thus be obtained as a relatively pure compound by extraction. No data could be found concerning its physical properties, but further purification by column chromatography is expected to be effective. If the compound is a solid, recrystallization will be attempted. c-substitution TM's Aldol/Claisen TM's Number Structure Number Structure COH
Synthesis using Carbonyla-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. My two target molecules are number 2 and number 12 in the last page. 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.
Synthesis using Carbonyla-Substitution Chemistry My submission for this assignment would look something like this: a-Substitution Synthesis John Doe Retrosynthetic Analysis (target 1): сон Ph FGI ROCCOR C-C ROCCO, Cc ROCCO, H. Proposed Synthesis: RO.CCOR (1) NOR ROCCOR (1) NOR HO* ROC COR Ph TM H H A (2) (2) Ph Br II BE Retrosynthetic analysis (target 2): = 2 => 0 OH 0 Br Proposed Synthesis: NOAC HO 0] base on 10 q TM Br OH A Proposal(Target 1): In the first step, diethyl malonate will be treated with sodium ethoxide in ethanol and 2-bromopropane will be added. After extraction with water and ether to remove any inorganic salts and removal of solvent, the product will be purified by distillation or vacuum distillation. The literature boiling point
Synthesis using Carbonyla-Substitution Chemistry for diethyl malonate is 200°C at atmospheric pressure (Sigma Aldrich), so the expected boiling point of the product will be slightly higher. In the second step, the same approach will be taken. The product I will treated with sodiu ethoxide in ethanol, followed by benzyl bromide. After washing a solution of the compound to remove inorganic salts and evaporation of solvents, purification by vacuum distillation is likely to be the most appropriate choice for this high molecular-weight compound. In the third step, the product II will be heated under reflux with dilute acid. The carboxylic acid product will be extracted into a basic solution and washed with an organic solvent such as ether in order to remove any unreacted starting material. After acidification, the product (2-benzyl-3- methylbutanoic acid) will become soluble in organic solvents and can thus be obtained as a relatively pure compound by extraction. No data could be found concerning its physical properties, but further purification by column chromatography is expected to be effective. If the compound is a solid, recrystallization will be attempted.
Synthesis using Carbonyla-Substitution Chemistry a-substitution TM's Aldo/Claisen TM's Number Structure Number Structure 11 H сон You 2 my molecules 12 اللہ COH CO,H 3 13 H 14 CO,H OH O 15 Y COET 6 "CO,H 16 HO 7 8 li 9 be 10
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The answer is explained in the images.Given com compound- Retrosynthers scheme FGT CH₃ Br COOH £{ cqe Etol cou U H X +24 CORET forward scheme :- Etzole copet Ctonand then In third step: - The product from step at will be taken in a Round bottom flask dil Ha solution will be added. and t

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