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Exam%20II%20Key

Exam%20II%20Key - 1(20 points Provide and arrow-pushing...

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Unformatted text preview: 1) (20 points). Provide and arrow-pushing mechanism for the acid-catalyzed conversion of A to B. For each intermediate, you must either a) show only the most stable resonance contributor or b) if you show multiple resonance structures (which is fine), you must identify the most stable resonance contributor. a W (W OWoH H23 O4( ()cat 2) (25 points). Draw the product(s) or provide the reagents required to complete each of the following transformations. 3 ——————-» l A H30 OCH:HC OOOH- M o H C\/u\/CH 3 3 ch CH3 HO o o H2NNH2 ————> CH3 KOt—Bu 200°C wcq} 3) (10 points). Arrange the following molecules in order of increasing reactivity toward hydration (1 = slowest, 4 = fastest). i H3C O H (1L CH3 HgCJkCHs O 3 4) (10 points) Circle the more acidic molecule from each pair. .4 O OOH 5) (15 points). The synthesis of phenyl lithium from reaction of bromobenzene and lithium metal (this process is similar to Grignard formation) is typically accompanied by formation of biphenyl as a byproduct. Provide an arrow-pushing mechanism that accounts for this transformation. Hint: phenyl lithium is a very strong base. 6) (20 points). Show the carbinolamine, iminium ion, and product of the reaction of N-methylaniline with 3-pentanone in the presence of dilute acid catalysis. if any of these compounds can be described by more than one resonance structure, show only the most stable contributor. carbinolamine iminium ion 7) (15 points). Provide arrow-pushing mechanism for the conversion of oxirane A to methylenecyclohexane upon treatment with triphenylphosphine (hint: PPha is a nucleophile). '\y if S 8) (20 points). Treatment of 2,3-dlchlorobenzonitrile with 3—methylbutanethiolate leads to substitution of one and only one chlorine atom. Show the product of this reaction and show the most stable, and only the most stable resonance structure of the key intermediate in this transformation. intermediate 9) ’ (15 points). Show the anionic and cationic intermediates generated by H20 addition to cyclopentanone under base and acid catalysis, respectively. p Q o 5') on 13‘ o OLIZ H20/H30+ H2O/OH' / ...
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