Ochem Test 3

Front 1

Add H2O to alkene

Back 1

Mark

Front 2

Reactivity of Electrophiles

Back 2

Best have:
1. Electrophilic carbon
2. Good leaving group

Front 3

Strength of nucleophile rules

Back 3

1. Negative charge is good
2. Opposite of electronegativity
3. Polarizability is good BUT NOT FOR BASES
4. Hindered is bad; OPPOSITE FOR BASES

Front 4

Leaving group rules

Back 4

1. Electron withdrawing
2. Stable after leaving (not a strong base)
3. Polarizable (to stabilize transition state

Front 5

SN2 Stereochemistry

Back 5

Yes;
Walden Inversion

Front 6

SN1 Stereochemistry

Back 6

Could do retention or inversion (50/50)

Front 7

E2 Stereochemistry

Back 7

Anti-coplanar, syn-coplanar stuff;
Anti-coplanar is favored

Front 8

Add H2, Pt/Pd/Ni to alkene

Back 8

Front 9

Add HOOH to alkene

Back 9

Front 10

Oxidative Cleavage (O2)

Back 10

Front 11

Add R-COOOH to alkene

Back 11

If you then add H3O+, makes a glycol (anti dihydroxylation)

Front 12

Add X2 to alkene

Back 12

Stereochemistry: anti

Front 13

Add X2, H2O to alkene

Back 13

Stereochemistry: anti
Mark on respect to OH

Front 14

Add HX to alkene

Back 14

Front 15

Cyclopropanation

Back 15

Front 16

Free Radical Addition of HBr (mechanism)

Back 16

Anti-Mark (because that puts the free radical on the more stable carbon)

Front 17

How to get more E2, less SN2?

Back 17

Use bulky base

Front 18

How to get more Hoffmann product in Alkene synthesis

Back 18

Use bulky base

Front 19

Add Hg (OAc)2, H2O, NaBH4 to alkene

Back 19

Also works with alcohols

Front 20

Add BH3 to alkene

Back 20

Anti-Mark

Then add O (usually in form of H2O2/-OH/H2O) to make anti-Mark alcohol

Front 21

Adding Br to a solution to test for DB

Back 21

No DB = color stays (no rxn)
DB = Clear (rxn)

Front 22

Addition of carbenes to alkenes (:CR2)

Back 22

Front 23

Making :CH2 from diazomethane

Back 23

Front 24

Simmons-Smith Reaction

Back 24

Does addition of carbene

Front 25

McPBA

Back 25

Metachlorobenzoic acid;
Epoxidates alkenes;
It with H3O+ works like cold, dilute KMnO4 (syn dihydroxylation)

Front 26

Add OsO4, H2O2 to alkene

Back 26

Front 27

Add KMnO4 to alkene

Back 27

1. Cold, dilute = syn dihydroxylation
2. Warm, concentrated = cleaves into two ketones

Front 28

Add O3, Me2S to Alkene

Back 28

Oxidative Cleavage

Front 29

Back 29

Olefin metathesis

Front 30

Make acetylide from R-CC-H

Back 30

Add NaNH2

Front 31

Acetylide + carbonyl group (ketone)

Back 31

Add another H+ to make a propanyl alcohol

Front 32

Synthesis of Alkyne?

Back 32

Eliminate vicinal or geminal dihalides using a base
1. KOH at 200 for internal
2. NaNH2 at 150, then H2O/H+ for terminal

Front 33

Add A-B to alkyne

Back 33

Front 34

Add H2, Pt to alkyne

Back 34

becomes alkane

Front 35

Add H2, Pd/BaSO4 to Alkyne

Back 35

Becomes cis alkene because it's poisoned

Front 36

Add NaNH3 to alkyne

Back 36

makes trans alkene

Front 37

Add X2 to alkyne

Back 37

Front 38

Add HX to alkyne

Back 38

Mark for terminal alkynes

Front 39

Add HgSO4, H2SO4, H2O to alkyne

Back 39

Front 40

Add R2BH to alkyne

Back 40

Front 41

Add KMnO4 to alkyne

Back 41

Front 42

Add KMnO4 and base to alkyne

Back 42