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in Black New Tab MyUn Sign in Learn @ cheggc GetH Mic x Sign .pdf 1) Choose one molecule from the set and create an 8-step synthesis scheme using the chosen molecule as your starting material. You need to write the complete set of reagents and draw the product expected from each step. Reagents typically used together are considered one step, e.g. 1) LAH 2) H20 should be considered as one step. Your 8 steps must include at least one reaction from each of the chapters, aldehydes and Ketones, carboxylic acid derivatives, alcohols. You can repeat a reaction only once therefore your scheme could have 2 oxidations maximum etc. ol OH SY он More specifically, your scheme can include: a) oxidations b) reductions c) Grignard reactions d) acetal formation/cleavage e) Wittig reactions f) reactions or synthesis of an acid chloride, ester, amide or anhydride g) a reaction with SOCl2 or PBr h) any reaction to synthesize or react alcohols i) Iminelenamine synthesis/hydrolysis j) novel reagents such as Gilman and modified reducing agents. 8-step Synthetic Scheme:

Answer 1

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MeOH Acetyl Chloride DIBAL-H DCM, -78 °C Esterification Step 1 Ester reduction to aldehyde Step 2 Wittig reaction Step 3 CH3PPh3Br t-BuOK THE HOO SOCI PDC DMF BH3. THE NaOH, H2O2 Step 4 Acid Chloride formation PDC, pyridinium dichromate oxidise primary alchol to acid. Oxidation Step 5 Step 6 H₂N ya Et3N, DCM Amide formation Step 7 ZI IZ EtMgBr (1 equiv) THE Griganard reaction Step 8 Mechanism for step 8 are one ou gone on one ZI -OMe

НО. С IR peaks 1. 3400-2800cm-? (broad peak, for OH streching) 2. 1720 cm1 for c=o Streching 7.80 doublet 7.36 doublet H (9.50 ppm singlet for aldehyde proton) H,с (2.50 ppm singlet for methyl proton) 7.80 doublet 7.36 doublet