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Unformatted text preview: the p-isomer is also favored.
δ+ δ+ O
δ+ CH3 H NO2 The meta-intermediate is not stabilized by the methoxy group, and so this intermediate is the least thermodynamically favored of the three. The m-isomer will be a minor product. Question 7 (21 points). Predict the outcome of seven of the following ten reactions, including any stereochemical or regiochemical outcomes. Br2, hν Br Br + NBS, AIBN CCl4, ∆ Br + Br 1) NaNH2/NH3 2) I O2N NO2 NO2 HNO3/H2SO4 ∆ O O AlCl3 SO3/H2SO4 ∆ OCH3 + SO3H NH2 CH3 Cl OCH3 + Cl CH3 HO3S OCH3 + Cl OCH3 NO2 CH3 OCH3 CH3 SnCl2/HCl Cl2 FeCl3 OCH3 CH3 KOH + CHCl3 CCl2 + CCl2 OCH3 OCH3 + Br AlCl3 OCH3 + OCH3 + OCH3 Question 8 (10 points). Provide structures for two of the following three names p‐chloronitrobenzene Cl NO2 1,3,5‐trimethyl‐2‐chlorobenzene Cl m‐nitrotoluene BONUS QUESTION (10 points). Design a rational synthesis for the following: and NO2 starting from O2N Cl You may use any reagents you deem appropriate, and you may use the back of the page. H2 1) NaNH2/NH3 2) CH3-I NH3 HBr/ether HBr/ether (hydride shift) Pd/BaSO4 Li H2SO4 H2SO4 HBr addition from any of the alkene species will yield the desired 3° alkyl bromide, but the disubstituted alkenes will yield mixtures. The trisubstituted alkene (the most stable fromed by equilibration with H2SO4 or H3PO4 will give one alkyl halide. See over for remainder of synthesis. Br Br + AlCl3 HNO3/H2SO4 + dialkylated product TARGET Cl2 O2N Cl FeCl3 O2N + o-isomer. Chromatography or recrystallization required....
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