- Joined
- Jun 23, 2010
- Messages
- 495
- Reaction score
- 21
All the other road maps are relatively straight forward.. But there's something wrong with either 5 or me (probably me
)
First question,
2-bromobutane is reacted with CH3SH/DMSO to give a butane with S-CH3 attached at the 2 carbon. Ok, that's fine and dandy, but why is it an SN2 reaction?? CH3SH is not a strong base, so wouldn't it do SN1?
Second question,
2-bromo-2-methylbutane is reacted with CN- / D to give 2-methyl-2-butene product through an E1 mechanism...
According to Chad, isn't CN- a strong nuc, but a weak base? So shouldn't the prefered reaction be SN2? But it is a tertiary halide, does that take preference over the fact that CN- is a good nuc?
Someone please save me.

First question,
2-bromobutane is reacted with CH3SH/DMSO to give a butane with S-CH3 attached at the 2 carbon. Ok, that's fine and dandy, but why is it an SN2 reaction?? CH3SH is not a strong base, so wouldn't it do SN1?
Second question,
2-bromo-2-methylbutane is reacted with CN- / D to give 2-methyl-2-butene product through an E1 mechanism...
According to Chad, isn't CN- a strong nuc, but a weak base? So shouldn't the prefered reaction be SN2? But it is a tertiary halide, does that take preference over the fact that CN- is a good nuc?

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