Chapter 6 & 7: Nucleophilic Substitution & Elimination Flashcards
SN2 reactions give…
stereochemistry
inverted stereochemistry in the product
SN1 reactions give…
stereochemistry
a racemic mixture
What is a useful function of TsCl?
To convert an OH into a suitable leaving group
What do SN2 reactions favor?
3 conditions
- Primary substrate
- Strong nucleophile
- Unhindered nucleophile
What do E2 reactions favor?
4 conditions
- Secondary or primary substrate
- Strong nucleophile
- Hindered nucleophile
- High temperatures
What do SN1 reactions favor?
3 conditions
- Tertiary substrate
- Weak nucleophile
- Low temperature
What do E1 reactions favor?
3 conditions
- Tertiary substrate
- Strong hindered base
- High temperature
What form do E1 reactions predominantly result in?
Most substituted alkene (Zaitsev product)
What form does a hindered base in E2 reaction result in?
Least substituted alkene (Hofmann product)
What form does an unhindered base in E2 reaction give?
Most substituted alkene (Zaitsev product)
What is imporant to consider with carbocations in E1 reactions?
The carbocation may rearrange to form a more stable one
Why would H2SO4 be used as an acid instead of HCl?
Cl is a nucleophile, so H2SO4 might be favored for elimination reactions so substitution does not occur
