(SYN) Show how each of these compounds can be produced from an alkene or alkyne. Draw the appropriate alkene or alkyne and include any necessary reagents and special reaction conditions. (a) (b) (c) (d) ОН HO
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- Consider the following reaction scheme: (i) Provide the reagent(s) required for this transformation. (ii) Draw a curved arrow mechanism and comment on the stereoselectivity.(b) Show how to synthesize the molecule at right, using the molecule at left as a carbon source, plus any other reagents without restriction. KOH H₂ EtOH Pd/C(SYN) Draw the structure of the carboxylic acid that can be reacted with diazomethane to form each of the following compounds. (a) (b) (c) HN OCH3 %3
- 1. Which of the following is not true about halohydrin formation of alkenes? (a) Water acts as a nucleophile. (b) The water attacks syn to the halide. (c) Water attacks the more substituted carbon. (d) The reaction is often performed in DMSO solvent. alating mIt is often helpful to have more than one way to make a given molecule, as you may not know ahead of time which strategy will be more successful.... 4-Hexyne-2-ol can be made from propene in two different ways – one by way of a bromohydrin, using a protecting group strategy, and another by using an epoxide (which does not need a protecting group strategy). (a) First, give the synthesis which goes through the bromohydrin and uses a protecting group. OH (b) Now, modify the synthesis (you may start with propene, or any other molecule you already made in part (a)) to accomplish the synthesis of 4-hexyne-2-ol using an epoxide.(b) Synthesize the following compounds from acetylene and any alkyl halides with four or fewer carbons. Note that more than one step may be required. HC=CH CH3CH2CH2CCH2CH2CH2CH3
- (c) (SYN) Show how to synthesize each of these species from an alkyl halide. (b) (a) OpPh3 PPH3 H2C PPh3Draw the complete, detailed E1 mechanism for each of the following reactions. (a) (b) I -Br CH3OH H20Resveratrol is an antioxidant found in the skin of red grapes. Its anticancer, anti-inammatory, and various cardiovascular effects are under active investigation. (a) Draw all resonance structures for the radical that results from homolysis of the OH bond shown in red. (b) Explain why homolysis of this OH bond is preferred to homolysis of either OH bond in the other benzene ring.
- (a) Suggest a retrosynthesis of product A shown below leading to the starting material on the left, and provide the synthesis of the desired product. You may use any other reagents you deem necessary and no detailed mechanism is required. AThe saccharide shown here is present in some plant-derived foods. (a) Indicate the anomeric carbon atom(s) in this structure by drawing a circle around the atom(s) or by drawing an arrow pointing to the atom(s). (b) Would this saccharide give a positive result with Benedict’s reagent? Why or why not? (c) Would this saccharide give a positive result with Barfoed’s reagent? Why or why not? (d) Would this saccharide give a positive result with Seliwanoff’s reagent? Why or why not? (e) In a separate set of experiments, the saccharide solution was treated with a reagent that breaks glycosidic bonds. After this treatment, would any of the three assays give different results? Be sure to indicate which assay results would be different and give a reason.Please provide a complete, detailed curved-arrow mechanism for the following reaction. Include ALL lone pairs and formal charges. Using the mechanism and a few words, explain why the NaOH deprotonates at the a-position and not the b-position or the aldehyde hydrogen. Also, explain why the indicated alkene is formed in the 2nd second rather than the other possible alkene product.