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19 Nov 2019
Stereochemistry
radical bromination of the following compound introduces bromine primarily at the be position next to the aro- matic ring. If the reaction stops the monobromination Stage, two stereoisomers result. benzylic position H H Br, HO H (a) Propose a mechanism to show why free-radical halogenation occurs almost exclusively at the benzylic position. (b) Draw the two stereoisomers that result from monobromination at the benzylic position. (c) Assign R and Sconfigurations to the asymmetric carbon atoms in the products. (d) What is the relationship between the two isomeric products? (e) Will these two products be produced in identical amounts? That is, will the product mixture be exactly 50:50? (n Will these two stereoisomers have identical physical properties like boiling point. melting point, solubility, etc.? Could they be separated (theoretically, at least by distillation or recrystallization? 3.4 Dimethylpent-1-ene has the formula CH CH-CH(CH)- CH(CHs)1. When pure (R-3A-dimethylpent-l-ene is treated with hydrogen over a platinum catalyst, the product is (S-2.3-dimethylpentane. (a) Draw the equation for this reaction. Show the stereochemistry of the reactant and the product. on, or has it been inverted figuration during this h b) Has the chirality center retained its con (e) The reactant is named (R), but the product is named (s). Does this name change imply a change in the spatial arrange- ment of the groups around the chirality center? So why does the name switch from (Rolo sign of the (d) How useful is the (R) or (s designation for predicting the sign of optical you predict the rose/By rotation of the reactant? of the product? (Hint from Juliet Capulet: "What's in a name? That which we call a any other name would smell as sweet.) chiral hydrocarbon exhibits a molecular ion at 82 in the mass spectrum. The IR spectrum shows peaks at 3300, 3000-2850, and 2250 cm''. Propose a structure for this compound.
Stereochemistry
radical bromination of the following compound introduces bromine primarily at the be position next to the aro- matic ring. If the reaction stops the monobromination Stage, two stereoisomers result. benzylic position H H Br, HO H (a) Propose a mechanism to show why free-radical halogenation occurs almost exclusively at the benzylic position. (b) Draw the two stereoisomers that result from monobromination at the benzylic position. (c) Assign R and Sconfigurations to the asymmetric carbon atoms in the products. (d) What is the relationship between the two isomeric products? (e) Will these two products be produced in identical amounts? That is, will the product mixture be exactly 50:50? (n Will these two stereoisomers have identical physical properties like boiling point. melting point, solubility, etc.? Could they be separated (theoretically, at least by distillation or recrystallization? 3.4 Dimethylpent-1-ene has the formula CH CH-CH(CH)- CH(CHs)1. When pure (R-3A-dimethylpent-l-ene is treated with hydrogen over a platinum catalyst, the product is (S-2.3-dimethylpentane. (a) Draw the equation for this reaction. Show the stereochemistry of the reactant and the product. on, or has it been inverted figuration during this h b) Has the chirality center retained its con (e) The reactant is named (R), but the product is named (s). Does this name change imply a change in the spatial arrange- ment of the groups around the chirality center? So why does the name switch from (Rolo sign of the (d) How useful is the (R) or (s designation for predicting the sign of optical you predict the rose/By rotation of the reactant? of the product? (Hint from Juliet Capulet: "What's in a name? That which we call a any other name would smell as sweet.) chiral hydrocarbon exhibits a molecular ion at 82 in the mass spectrum. The IR spectrum shows peaks at 3300, 3000-2850, and 2250 cm''. Propose a structure for this compound.
Tod ThielLv2
11 Mar 2019