Use LEFT and RIGHT arrow keys to navigate between flashcards;
Use UP and DOWN arrow keys to flip the card;
H to show hint;
A reads text to speech;
23 Cards in this Set
- Front
- Back
Rate of reaction for Sn2?
Stereochemistry of Sn2? Number of steps Sn2? |
Rate=K[nuc][R-LG]
Inversion of Stereochemistry One step (nuc attacks and LG leaves simultaneously) |
|
Mechanism of E2
Configuration of bond for E2 |
Base attacks beta-H electrons move to form double bond
Configuration dependent on alignment (beta-H trans or cis to LG) |
|
What happens if there is more than one beta-H for E2?
What happens if there is more than one beta-C for E2? |
Both stereochemistries
the more substituted beta-C has its hydrogen removed because it is better at delocalizing the charge of the carbocation |
|
Sn1 vs. E1
|
LG leaves in both leaving a carbocation and LG-
Sn1 Racemic mix of attached nucleo (different stereo) Eq E double bond plus Z diasteriomer |
|
1* with....
Good nuc, weak base Poor nuc, protic solvent Strong base unhindered Strong base |
Sn2
Slow Sn2 Sn2/E2 E2 |
|
2* with....
Good nuc, weak base Poor nuc, protic solvent Strong base unhindered Strong base |
Sn2
Slow Sn1 E2(Sn2) E2 |
|
3* with....
Good nuc, weak base Poor nuc, protic solvent Strong base unhindered Strong base |
Sn1
Sn1/E1 E2 E2 |
|
What are good nucleophiles but weak bases?
|
P, N, S, N3, Cn, I
|
|
WHat are protic solvents?
|
ROH, H20 has NH or OH bonds
|
|
What is a strong base unhindered
|
OH-
|
|
What is an example of a big strong base
|
tBuO
|
|
What mechanism does heat favor?
|
Elimination
|
|
How can you speed up Sn1/E1
|
Polar protic solvents (stabilization of the carbocation)
|
|
Reagent: H30+ or H20/H2SO4
|
E/N: H/OH
Regioselectivity: Markonikov Stereoselectivity: C-->not stereo enantiomer (1 chiral) |
|
Reagent: H-X
|
E/N: H/X
Regioselectivity: Markonikov Stereoselectivity: C+ intermediate enantiomer (1 chiral) |
|
Reagent: 1) BH3 2)NaOH,H202, H20
|
E/N: H/OH
Regioselectivity: Anti-Markonikov Stereoselectivity: syn enantiomer (2 chiral) |
|
Reagent: KMnO4 or OsO4
|
E/N: OH/OH
Regioselectivity: None Stereoselectivity: syn enantiomer |
|
Reagent: R-C=O-OOH
|
E/N: O
Regioselectivity: None Stereoselectivity: None enantiomer; 2C+O triangle |
|
Ozone
|
E/N: O/O
Regioselectivity: None Stereoselectivity: None Ph-H3C-C=O + H(or OH if H2O2 reagent)-C-H3C=O |
|
H2/Pt
|
E/N: H/H
Regioselectivity: none Stereoselectivity: syn |
|
X2/H2O
|
E/N: X/OH
Regioselectivity: Markonikov Stereoselectivity: anti enantiomer |
|
X2
|
E/N: X/X
Regioselectivity: None Stereoselectivity: anti enantiomer |
|
X2/ROH
|
E/N: X/OR
Regioselectivity: Markonikov Stereoselectivity: anti enantiomer |