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Please help I need any idea of what to do

CHE 282- Spring 2018-Labo: Planning Multistep Synthesis of an Organic compound. 18 points Due Week of April 23 before start of Lab 10 (Late assignments penalty- 1 point per hour) Name Partner: TA: You are Student 1 Complete and submit this worksheet Attach more sheets of paper as needed L7.Leonides L7-Leonides Problem 1: Using any technique and chemical reaction(s) covered in CHE 201-202 prepare a proposed synthetic plan to show a multistep synthesis of the target compound from 100 mmoles of starting material. Target Compound is a fictitious component used in the preparation of a very important&expensive antitumor drug. It is important that your proposed synthesis should be efficient and not have too many steps, demonstrate how you would purify and analyze the products and intermediates (for each step). PART A: 5 points (replaces pre-lab quiz 2) Provide an efficient and theoretically correct Retrosynthetic Analysis (chemical structures) of your assigned Target, also discuss the importance of the target (You can improvise and use your imagination), discuss your retrosynthetic plan PART B: 13 points (replaces data sheet, note book, performance and lab report points) 1. Discuss your synthetic plan and chemistry of reactions involved in the synthesis. Show Proposed Synthetic Sequence (chemical structures)with reagent and conditions. 5 points 2. Provide a detailed procedure (Preparation, Purification & Analysis) of the first half of the reactions in the scheme. assume all reactions in the synthetic plan will have a 90 % yield in each step. 5 points . Procedure should include quantities (with correct stoichiometry) of chemicals required. 2. Mention all the techniques required during preparation, purification and Analysis 3. Name all the glassware used, 4. Provide a data table, it should list all the reagents and the required quantities needed for the preparation, purification and analysis. 3. Discussion, 3 points each student 3/23/2018 Ahsan-Riaz-CHE 202 Springl 2018-Lab 6-UB

Answer 1

Dear Student,

Problem 1:- you can see below-attached image where a 6 steps synthetic plan has been written, all these compounds can be characterised by 1H NMR, 13C NMR and IR. and can be purified by the column chromatography. all compounds are UV active so you can easily detect the reaction completion with the help of Thin layer chromatography.

you can see below-attached image where a 6 steps synthetic plan has been written, all these compounds can be characterised by 1H NMR, 13C NMR and IR. and can be purified by the column chromatography. all compounds are UV active so you can easily detect the reaction completion with the help of Thin layer chromatography. Proposed synthesis plan Retrosynthesis Analysis part A: - this target molecule can synthesis by esterification of the corresponding acid, and that acid can synthesis by oxidation of alcohol in presence of KMnO4, That corresponding alcohol we can get by deportation reaction in presence of BBr3, methoxide protected compound we can get by the alkylation reaction in presence of benzene. and the first step of this synthesis we can get by the Diels-alder reaction. all the retrosynthesis plan you can see in the below given Image. part B: - this is forward synthesis plan for the synthesis of the target molecule, where started from diene reacted with a dienophile gives us dials alder adduct that adduct where protected with methyl iodide,

part A:- this target molecule can synthesis by esterification of the corresponding acid, and that acid can synthesis by oxidation of alcohol in presence of KMnO4, That corresponding alcohol we can get by deprotection reaction in presence of BBr3, methoxy protected compound we can get by the alkylation reaction in presence of benzene. and the first step of this synthesis we can get by the Diels-alder reaction. all the retrosynthesis plan you can see in the below given Image.

part B:- this is forward synthesis plan for the synthesis of the target molecule, where started from diene reacted with a dienophile gives us diels alder adduct that adduct where protected with methyl iodide, and the protected compound where treated as Grignard fashion and attached on benzyne to get the core structure of target molecules. that compound were treated with BBr3 to deprotect and then oxidation follows by esterification gives us target molecule.

Thank you

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