CHEM 316 - problem%20set%207%20reactions

CHEM 316 - problem%20set%207%20reactions - bond...

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Chem 316 OH O O CO 2 H N O OH N O N O OHC Br O NH F I Cl Br N(CH 3 ) 2 OCH 3 1. Identify sites in each molecule that can act as nucleophiles and electrophiles. F 2. Rank each of the following sets of reactive intermediates from most to least stable: I set 1: Cl set 2: Br set 3: N(CH 3 ) 2 set 4: OCH 3 set 5: set 6: Problem Set 7: Reactions Chem 316
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Chem 316 H CH 3 CH 2 Br H Br CH 3 CH 3 H 3. Show the electron flow (add the appropriate arrows and any missing intermediates) to show the mechanisms for the following reactions. Classify each reaction as an addition, elimination, or substitution. a. + H-Br Br Br + which product will be the major isomer? b. + H-Br Br Br + why doesn't form? Br c. OH + H 2 SO 4 + H + d. + Br 2 h υ Br a. show the mechanism of each (propagation steps only); b. calculate H for each propagation step (use Wade Table 4-2, p. 142, and these
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Unformatted text preview: bond dissociation energies: PhCH 2 Br = 58 kcal/mole; BrPh = 81 kcal/mole; "Ph" stands for the phenyl group); c. calculate the overall H for each reaction; d. draw an approximate energy diagram for the two propagation steps of each reaction, putting both curves on the same graph; e. briefly explain which reaction (I or II) happens faster; f. briefly explain which reaction (I or II) gives a more stable product. Br II) + e. O + Br 2 1. H 3 C-Li + 2. H 2 O OH + HBr CH 3 + HBr f. O + Br 2 + [(CH 3 ) 2 ] -[CuLi] + O-[CH 3 CuLi] + I) CH 3 4. For these two reactions: H 2 O O h CH 3 h...
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CHEM 316 - problem%20set%207%20reactions - bond...

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