SN2 vs. SN1
"What is the product when (2R,3R)-2-bromo-3-methylpentane is reacted with NaOH?"
QId: 402692 (2123333)
Would someone mind explaining to me how you know that this reaction would proceed via an SN2 mechanism vs. an SN1 mechanism? I thought because it's a secondary substrate that's sort of sterically hindered that it would proceed via SN1 but the answer has it proceed via SN2 (thus inverting the product).
Thank you for your help I REALLY appreciate it!!
There are three things that you should consider when determining whether a reaction proceeds via SN1 vs SN2
1. Is access to the leaving group sterically hindered? Typically, primarily substituted LGs will be very easy to access, and tertiary near impossible. Secondary is in the middle, but in this particular case there are only two methyls in the way, which means steric hindrance is really low.
2. How sterically hindered is the base? in this case, we have hydroxide, a very small base that can easily access the mildly hindered secondary substituted LG site. Again, this pushes us towards SN2.
3. Finally, how strong/charged is the nucleophile? Strong, charged nucleophiles almost always proceed via SN2. Weak, uncharged nucleophiles proceed via SN1. Hydroxide is an incredibly good nucleophile, again pointing to SN2
pages:
1