Provide a synthesis for the target molecule shown below, starting with an alkyl halide or alcohol of your choice. In each case, show your retrosynthetic analysis, and then provide a complete synthesis, showing all necessary reagents. { Which of the following syntheses are suitable to prepare the given target molecule (as the major product formed)? Select all that apply. 0 0 0 O 1) TsCl, pyridine OH 2) NaOEt OH -CI 1) TsCl, pyridine 2)1-BuOK NaOH t-BuOK conc. H₂SO4 Pots OH heat t-BuOK

Starting with benzene and using any other reagents of your choice, design a synthesis for the following compound: COOH NO₂ COOH The target molecule above can be prepared by treating benzene with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A Mel, AlCl3 B KMnO4, NaOH, heat (followed by H3O+ workup) C HCI, Zn D E F (CH3)2CHCI, AICI 3 HNO3, H2SO4 Fuming H2SO4

Provide a synthesis for the target molecule shown below, starting with an alkyl halide or alcohol of your choice. In each case, show your retrosynthetic analysis, and then provide a complete synthesis, showing all necessary reagents. Which of the following syntheses are suitable to prepare the given target molecule (as the major product formed)? Select all that apply. U U U 3 Br Br t-BUOK OH Br t-BuOK NaOH LOH conc. H₂SO4 heat Br NaOEt conc. H₂SO4 heat

Using Ethylene, C2H4, and methyl bromide, CH3Br, as your sole sources of carbon, propose a synthesis for t-BuOH, (CH3)3COH. *the synthesis should take about 7 steps and will include an alkylation and a Grignard reaction. Use one equivalent of methyl bromide for the alkylation step and use the second one to make the Grignard reagent. The substrate in the Grignard reaction will be a carbonyl - make this from your alkyne AFTER alkylation. *show all reactants and intermediates H +2 H H Br -7 steps H₂C H₂C OH CH3