4. The anisole derivative below undergoes a selective cross coupling reaction on only one of the two bromides. Predict the structure of the product and explain why that is the mechanistically preferred product. OMe Pd°Ln, PhB(OH), (1 equiv) biaryl product Br K,PO,. THFM,0, 80 °c Br
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- The anisole derivative below undergoes a selective cross coupling reaction on only one of the two bromides. Predict the tructure of the product and explain why that is the mechanistically preferred product. OMe Pd Ln, PhB(OH)2 (1 equiv) biaryl product Br KgPO, THF/H,O, 80 °C BrWhich conditions will cause the interconversion shown? how? H H2/ Lindlar catalyst oa. Li/ NH3lia) ob. H2 / PtO2 (1) Brg: (2) KOH / E:OH od. (1) Hg(OAc)2 / THF / H2O: (2) NaBH4 е.Under basic conditions, the following substrates can undergo a [4+2] cycloaddition with regio- and diastereo- control. Rationalize mechanistically how the reaction occurs as well as the regio- and stereochemical outcome with each base. CHO Na-co- >> 20:1 dr 20:1 m CO₂Et OF CHO 0: nao > 20:1 dr >> 20:1 13500 DBU is an amine-like base; please abbreviate NR-
- NaN3 НО. NH compound c compound d CI H₂, Pt -85 [References] compound a SOCI₂ SOCI₂ compound d compound e Moclobemide compound b CI The above reaction scheme presents one possible synthesis of the compound. Work out the synthesis on a separate sheet of paper, and then draw the structure of compound e. Consider E/Z stereochemistry of alkenes. • Do not show stereochemistry in other cases. {n [F ? ChemDoodleⓇYou must prepare the most stable possible alkene starting from the starting material given below and following an E2 elimination reaction. H Base Ö most stable alkene CH3 Ph Et Br PhDraw the sigma complex for the formation of the bromonium electrophile with proper resonance forms for the meta bromination of toluene and for the para bromination of toluene. Which resonance structure places the (+) next to the methyl group? Will either one (i.e. para and meta sigma complex) yield a fourth resonance structure? Given that alkyl groups such as CH3 are electron rich (i.e. no attached electronegative atoms), which sigma complex in part (A) would be more stable?
- The nitration of furan leads preferentially to the formation of 2-nitrofuran rather than the 3-nitro isomer. Explain this result by considering the stability of the arenium leading to each isomer. O. NO2 NO2 Prackia oo175. What dien and dienophile should be used to synthesize the following compounds? Explain the stereo-and region-chemistry of each reaction. CH3 CN OMe &Mechanism. Propose a mechanism for the following reaction. Label the rate-determining step and the major resonance contributor. Make sure to include (1) the formation of the electrophile and (2) all significant resonance contributors of the sigma complex intermediate. NO2 H2N H2N. HNO, (1 eq.) H2SO4 O °C CF3 CF3
- Provide the reagents necessary to carry out the conversion shown. 1. H2O; 2. KMnO4 1. O3; 2. DMS; 3. Na2Cr2O7/H2SO4/H2O 1. NaOH, Br2; 2. DMS; 3. H2O/heat 1. O3; 2. DMS; 3. KMnO4 1. DMS; 2. H2O2/heatIrradiation of diene A at 254 nm affords a photostationary mixture of A with triene B. Provide a mechanism for the formation of B and define the stereochemistry of the alkenes, explaining this stereochemical outcome by reference to the interacting frontier molecular orbitals. H. hv H B3. Provide the products for the following reactions. Provide the correct stereochemistry where necessary. HBr 1.) NaBr / DMSO 2.) H₂O excess HI