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32 Cards in this Set

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IF ADDITION, what should you first look for?
break pi bond.
IF ELIMINATION, what should you first look for?
make pi bond
IF SUBSTITUTION, what should you first look for?
different groups
Substrate: alkene
Reagent: HX
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
1. H/X
2. None (carbocation rearrang possible)
3. Markovnikov
Substrate: alkene
Reagent: HBr + peroxides
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
1. H/Br
2. None: C radical intermediate. no radical rearrang.
3. Anti-markovnikov
Substrate: alkene
Reagent: H2O + acid
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
1. H/OH
2. None: C+ rearrang.
3. Markov
Reagents: Hg(OAc), THF/H2O
NaBH4, OH-
Substrate: alkene
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
Oxymercuration/demercuration
1. H/OH
2. None => no possibly for carbocation rearrangment.
2. Markov
Reagent: BH3, H2O2, OH-
Substrate: alkene
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
hydroboration
1. H/OH
2. Syn addition
3. Antimarkovnikov
Whenever you have a carbocation intermediate, what should you think?
Always think:
1. RACEMIC PRODUCT
2. C+ rearrangement (if can make more stable, it will!)
if the product is different than you originally thoguht it would be, what should you think?
carbocation rearrangement!
Reagent: H2 + metal catalyst (Pb, Ni, Pt)
Substrate: alkene
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
1. H/H
2. Syn addition (alkyne => alkane)
3. n/a
Reagent: H2 + Lindlar catalyst (CaCO3, BaSO4, Pd)
Substrate: alkene
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
1. H/H
2. Syn addtion to alkyne stop at alkene.
Reagent: Na, NH3
Substrate: alkene
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
1. H/H
2. Anti-addition to alkyne => alkene
3. ---
Reagent: X-X
Substrate: Alkene
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
1. X/X
2. Anti-addition halonium intermediate~epoxide ring.
Reagent: mCPBA
Substrate: Alkene
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
1. OH/OH
2. anti-addition (epoxide intermediate)
Reagent: KMnO4
Substrate: Alkene
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
1. OH/OH
2. Syn addition
3. ----
Reagent: O3
Substrate: Alkene
1) What does it add to pi bond?
2) Stereoselect?
3) Regioselectivity (what side of dlb bond is it going to add to?)
THIS BREAKS DOUBLE BONDS INTO KETONES.
Oxidation of a primary alcohol gives what?
aldehyde => carboxylic acid
Oxidaiton of a secondary alcohol gives what?
ketone
What are the conditions that all aromatic compounds have to satisfy?
1. cyclic => every atom in ring must have unhybridized p orbital.
2. flat and planar (no higher than sp2 hybrid)
3. Huckel's # of electrons (4n+2)
(T/F) For aromatic compound, if lone pair contributes to resonance than it isn't hybridized
True; so if the lone pairs in nitrogen contribute to resonance, and its attached to three other atoms ==> it is sp2 hybridized (not sp3).
- You do count those lone pairs in the huckel number (max one pair though).
When one of the double bonds on benzene attacked Br-Br, it forms a ______; but b/c this is a bad resonance form it will _______.
carbocation; elimination.
Electron donating groups are ring _______.
activators;
the ring will become more reactive; (You can draw out the resonance structures if you'd like to visualize)
- Electron donating groups have lone pairs on ______ atom.
- Exception?
alpha;
- exception: R groups are electron donating; they activate the ring.
- Electron withdrawing group have lone pairs on ______ atoms.
- Exceptions?
Beta;
- exception: halogens are ring deactivators b/c they are very electronegative
Electron withdrawing group ____ the ring.
- deactivate the ring; make it less reactive.
- will direct towards met position
WHat is the extend of H-bonding for aldehydes/ketones?
They can accept H's but can't donate H's.
(T/F) Aldehydes/ketones are more soluble than alkanes/enes in water.
True.
(T/F) BP/MP of aldehydes/ketones is less than alcohols.
True b/c alcohols can H-bond.
What should you always do when evaluating acidity?
DRAW THE CONJUGATE BASE AND DECIDE IF ITS STABLE.
If you see an OH bonded next to dbl bond, what should you immediate thing.
That its really a ketone/aldehyde... DO NOT THINK ALCOHOL and DOUBLE BOND B/C THE ALDEHYDE/KETON IS SO MUCH MORE REACTIVE!!!
WHEN SEE AN AN ALCOHOL BONDED NEXT TO A DOUBLE BOND, what kind reaction are you going to get?
- You should first thing: it's a aldehyde/ketone b/c those are more reactive.
- Therefore you should get nucleophilic addition not elimination/substitution!!!