Question
Pencil and paper ready. You are performing an SN2 (“S-N-two”) reaction using OH-minus as a nucleophile and [read slowly] (R)-2-bromobutane (“R-two-bromo-butane”) as the reagent. For 10 points each:
[10h] The SN2 reaction between OH-minus and (R)-2-bromobutane produces a bromide ion and what product? Please give the IUPAC (“I-U-pack”) name, including stereochemistry. You have 10 seconds.
ANSWER: (S)-2-butanol (“S-two-butanol”) [or (S)-sec-butanol or (S)-2-butyl alcohol; accept (S)-butan-2-ol; prompt on 2-butanol or sec-butanol or 2-butyl alcohol by asking “what is the stereochemistry?”; reject “(R)-2-butanol” or similar answers that use “(R)” in place of “(S)”]
[10m] If you run the reaction with a bulky nucleophile like DBU, you may instead cause this type of reaction that competes with substitution. The product of this type of reaction would be an alkene.
ANSWER: elimination reaction [prompt on E1 or E2 by asking “what does the E stand for?”]
[10e] Aprotic solvents like DMSO or this solvent will promote the SN2 reaction over SN1 or E1. This solvent is the simplest ketone (“kee-tone”) and is used in nail polish remover.
ANSWER: acetone [or 2-propanone or dimethyl ketone; accept (CH3)2CO (“C-H-3-2-C-O”)]
<Chemistry>
Summary
| 2023 ACF Winter @ Columbia | 11/11/2023 | Y | 8 | 23.75 | 100% | 88% | 50% |