Question
To prevent one of these intermediates from rearranging during a Friedel–Crafts alkyl·ation, you can perform an acyl·ation instead and then reduce the ketone. For 10 points each:
[10m] Name these intermediates formed under acid catalysis that rearrange via hydride or methanide shifts.
ANSWER: carbo·cat·ions [or carbenium or carbonium ions; accept arenium ions or Wheland intermediates; prompt on cations or ions]
[10e] Carbo·cat·ions rearrange to let this atomic orbital on the carbon accept electrons from nearby pi or sigma-star orbitals. A carbocation’s bonding orbitals are hybridized from one s orbital and two of these atomic orbitals.
ANSWER: p orbitals [accept 2p orbitals]
[10h] Unlike in carbocations, the [emphasize] more substituted alkyl group shifts to an electron-deficient oxygen in the concerted final step of this named reaction. Migratory aptitude is often taught in the classroom in the context of this reaction.
ANSWER: Baeyer–Villiger reaction [or Baeyer–Villiger oxidation; or Baeyer–Villiger rearrangement; or BV oxidation]
Data
| Team | Opponent | Part 1 | Part 2 | Part 3 | Total |
|---|---|---|---|---|---|
| Chicago B | Ohio State A | 10 | 10 | 0 | 20 |
| Columbia B | Michigan A | 0 | 10 | 0 | 10 |
| Cornell A | Duke A | 0 | 10 | 0 | 10 |
| Cornell B | Minnesota A | 10 | 10 | 0 | 20 |
| Georgia Tech A | Florida A | 10 | 10 | 0 | 20 |
| Harvard A | Toronto A | 10 | 10 | 0 | 20 |
| Illinois A | South Carolina A | 0 | 10 | 0 | 10 |
| Imperial A | Florida B | 10 | 10 | 0 | 20 |
| Iowa State A | Penn State A | 0 | 0 | 0 | 0 |
| MIT A | Indiana A | 10 | 10 | 0 | 20 |
| Maryland A | Brown A | 0 | 10 | 0 | 10 |
| McGill A | Claremont A | 0 | 10 | 0 | 10 |
| Minnesota B | Houston A | 10 | 10 | 0 | 20 |
| North Carolina A | Columbia A | 10 | 10 | 0 | 20 |
| Northwestern A | Texas A | 10 | 10 | 0 | 20 |
| Penn A | Georgia Tech B | 10 | 10 | 0 | 20 |
| Rutgers A | Yale B | 0 | 10 | 0 | 10 |
| Rutgers B | NYU A | 10 | 10 | 0 | 20 |
| Stanford A | Yale A | 10 | 10 | 0 | 20 |
| UC Berkeley A | Chicago C | 10 | 10 | 0 | 20 |
| UC Berkeley B | Johns Hopkins A | 10 | 10 | 0 | 20 |
| Vanderbilt A | Purdue A | 10 | 10 | 0 | 20 |
| WUSTL A | Chicago A | 10 | 10 | 0 | 20 |
| WUSTL B | Virginia A | 10 | 10 | 0 | 20 |