For 10 points each, answer the following about solvent effects on the reaction of (S)-2-chlorobutane with sodium iodide:
[10h] If DMSO is the solvent, the reaction occurs through this simple organic mechanism, and the stereocenter completely inverts to produce the (R)-enantiomer.
ANSWER: SN2 [or bimolecular nucleophilic substitution; prompt on substitution; prompt on nucleophilic substitution; prompt on SN; reject “SN1”]
[10m] If ethanol is the solvent, the reaction forms an achiral carbo·cat·ion as one of these species, so the product is racemic instead. In a multistep reaction, these stable chemical species occur at energy minima.
ANSWER: reaction intermediates [reject “intermediary”]
[10e] If strong base is present, the reaction yields butene, which is one of these compounds containing a carbon-carbon double bond.
ANSWER: alkenes [or olefins; reject “alkanes” or “alkynes”]
<Ethan Ashbrook, Science - Chemistry> ~20560~ <Editor: Adam Silverman>