Org Dwn

Front 1

IF ADDITION, what should you first look for?

Back 1

break pi bond.

Front 2

IF ELIMINATION, what should you first look for?

Back 2

make pi bond

Front 3

IF SUBSTITUTION, what should you first look for?

Back 3

different groups

Front 4

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?)

Back 4

1. H/X
2. None (carbocation rearrang possible)
3. Markovnikov

Front 5

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?)

Back 5

1. H/Br
2. None: C radical intermediate. no radical rearrang.
3. Anti-markovnikov

Front 6

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?)

Back 6

1. H/OH
2. None: C+ rearrang.
3. Markov

Front 7

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?)

Back 7

Oxymercuration/demercuration
1. H/OH
2. None => no possibly for carbocation rearrangment.
2. Markov

Front 8

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?)

Back 8

hydroboration
1. H/OH
2. Syn addition
3. Antimarkovnikov

Front 9

Whenever you have a carbocation intermediate, what should you think?

Back 9

Always think:
1. RACEMIC PRODUCT
2. C+ rearrangement (if can make more stable, it will!)

Front 10

if the product is different than you originally thoguht it would be, what should you think?

Back 10

carbocation rearrangement!

Front 11

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?)

Back 11

1. H/H
2. Syn addition (alkyne => alkane)
3. n/a

Front 12

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?)

Back 12

1. H/H
2. Syn addtion to alkyne stop at alkene.

Front 13

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?)

Back 13

1. H/H
2. Anti-addition to alkyne => alkene
3. ---

Front 14

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?)

Back 14

1. X/X
2. Anti-addition halonium intermediate~epoxide ring.

Front 15

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?)

Back 15

1. OH/OH
2. anti-addition (epoxide intermediate)

Front 16

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?)

Back 16

1. OH/OH
2. Syn addition
3. ----

Front 17

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?)

Back 17

THIS BREAKS DOUBLE BONDS INTO KETONES.

Front 18

Oxidation of a primary alcohol gives what?

Back 18

aldehyde => carboxylic acid

Front 19

Oxidaiton of a secondary alcohol gives what?

Back 19

ketone

Front 20

What are the conditions that all aromatic compounds have to satisfy?

Back 20

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)

Front 21

(T/F) For aromatic compound, if lone pair contributes to resonance than it isn't hybridized

Back 21

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).

Front 22

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 _______.

Back 22

carbocation; elimination.

Front 23

Electron donating groups are ring _______.

Back 23

activators;
the ring will become more reactive; (You can draw out the resonance structures if you'd like to visualize)

Front 24

- Electron donating groups have lone pairs on ______ atom.
- Exception?

Back 24

alpha;
- exception: R groups are electron donating; they activate the ring.

Front 25

- Electron withdrawing group have lone pairs on ______ atoms.
- Exceptions?

Back 25

Beta;
- exception: halogens are ring deactivators b/c they are very electronegative

Front 26

Electron withdrawing group ____ the ring.

Back 26

- deactivate the ring; make it less reactive.
- will direct towards met position

Front 27

WHat is the extend of H-bonding for aldehydes/ketones?

Back 27

They can accept H's but can't donate H's.

Front 28

(T/F) Aldehydes/ketones are more soluble than alkanes/enes in water.

Back 28

True.

Front 29

(T/F) BP/MP of aldehydes/ketones is less than alcohols.

Back 29

True b/c alcohols can H-bond.

Front 30

What should you always do when evaluating acidity?

Back 30

DRAW THE CONJUGATE BASE AND DECIDE IF ITS STABLE.

Front 31

If you see an OH bonded next to dbl bond, what should you immediate thing.

Back 31

That its really a ketone/aldehyde... DO NOT THINK ALCOHOL and DOUBLE BOND B/C THE ALDEHYDE/KETON IS SO MUCH MORE REACTIVE!!!

Front 32

WHEN SEE AN AN ALCOHOL BONDED NEXT TO A DOUBLE BOND, what kind reaction are you going to get?

Back 32

- You should first thing: it's a aldehyde/ketone b/c those are more reactive.
- Therefore you should get nucleophilic addition not elimination/substitution!!!