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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!!!

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Deck Info

Number of cards 32