- Joined
- May 13, 2009
- Messages
- 356
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I wrote a Kaplan FL test today and they asked what would happen if a 2,3-dimethyl-2-butanol was reacted with HBr.
I assumed that it would undergo a Sn1 reaction because it was a tertiary alcohol and I was unsure about the strength of a bromide anion. But either way, it would be Sn1 because Sn2 cannot proceed with a tertiary carbon.
I was wrong. The answer was Sn2.
I am referring to this website: http://www.brynmawr.edu/Acads/Chem/mnerzsto/SN2vsE2_flowchart.htm
What's going on? Why is this Sn2? Is Kaplan just wrong (as usual)?
Furthermore, when do you know if something is base or a nucleophile? For example, HBr is an acid. I would assume that the Br- anion would be a base since it is technically a conjuage base of HBr. But in this case, the Br- anion acts as a nucleophile because no double bonds are made..
SO CONFUSED!!
I assumed that it would undergo a Sn1 reaction because it was a tertiary alcohol and I was unsure about the strength of a bromide anion. But either way, it would be Sn1 because Sn2 cannot proceed with a tertiary carbon.
I was wrong. The answer was Sn2.
I am referring to this website: http://www.brynmawr.edu/Acads/Chem/mnerzsto/SN2vsE2_flowchart.htm
What's going on? Why is this Sn2? Is Kaplan just wrong (as usual)?
Furthermore, when do you know if something is base or a nucleophile? For example, HBr is an acid. I would assume that the Br- anion would be a base since it is technically a conjuage base of HBr. But in this case, the Br- anion acts as a nucleophile because no double bonds are made..
SO CONFUSED!!