Packet 2: Bonus 1
Methyl iodide is used to exhaustively alkylate these species in a reaction that does not follow Zaitsev’s rule. For 10 points each:
[10e] The Hofmann elimination removes what ion that consists of a positively charged nitrogen atom and four substituents?
ANSWER: quaternary ammonium cations [accept quaternary ammonium salts or quaternary amines or quats]
[10h] This reaction can be used to elucidate alkaloid structure in cases where the Hofmann elimination fails. This reaction reduces quaternary ammonium cations into tertiary amines with sodium amalgam.
ANSWER: Emde (“EM-duh”) degradation [accept Emde reaction or Emde reduction]
[10m] Quaternary ammonium salts derived from Cinchona (“sin-KO-nuh”) alkaloids commonly act as these species. Crown ethers and cryptands can act as these species that facilitate movement from water to an organic solvent.
ANSWER: phase-transfer catalysts [or PTCs; prompt on catalysts]
<NYU A, Chemistry> | I2. Prelims Tiebreaker - NYU A + NYU B + Case Western + Cornell (Tiebreaker Half 2)
| Heard | PPB | E % | M % | H % |
|---|---|---|---|---|
| 1 | 10.00 | 0% | 100% | 0% |