Chem 3580 - Week 6

Front 1

Suzuki Reaction

Back 1

1. phenyboronic acid reacted with benezyl halide
2. Pd(PPh3)4 and NaOH = catalysts
3. product = two connected benzene rings

Front 2

Suzuki Reaction Mechanism

Back 2

1. dissosciation of organometallic complex
2. oxidative addition bw/ halide benzyl and metal
3. substitution of Br to OH
4. OH attaches to B, creating negative charge
5. nucleophilic attack; products: B(OH)3 and Pd(Ph2PPh3)
6. reductive elimination to get Pd(Ph3)2 and connected benzyls

Front 3

Olefin Metathesis

Back 3

1. couple two olefins together
2. split the double bonds down the middle
3. rearrange them in order to form new compounds

Front 4

olefin

Back 4

compound with a double bond

Front 5

Grubbs catalyst

Back 5

1. Ru bonded to 2 PCy3, 2 Cl, and CHPh ligands
2. Ru: Ru+4, d4, 16 e
3. ring closing metathesis
4. can release ring strain (ROMP)
5. trisubstituted reactions

Front 6

What is special about the CHPh ligand of the Grubbs catalyst?

Back 6

1. has a 2X oxidation value
2. allows for the Ru transition metal to be double bonded

Front 7

how is equilibrium of a Grubbs catalyst formed?

Back 7

1. if olefin products under go reverseibel association, cycloadditions, cycloreversions, and dissociations

Front 8

cylcoaddition

Back 8

forms a 4 membered ring

Front 9

cycloreversion

Back 9

breaks cycloring, and forms a new olefin product

Front 10

ring closing metathesis

Back 10

1. use in order to connect 2 double bonds within the same linear compound to form a ring, and a gaseous olefin
2. does not form trans double bonds

Front 11

Ring opening metathesis polymerization (ROMP)

Back 11

1. release ring strain within an unstable cyclic compound
2. forms a more stable polymer of rings

Front 12

trisubstituted reactions

Back 12

1. not very reactive
2. create ethylene as a product

Front 13

Alkene polymerization

Back 13

i. used to create a polymeric chain of carbons
ii. TiCli3, AlEt2Cl

Front 14

phenol

Back 14

1. benzene ring with a alcohol group directly attached to it
2. more acidic than regular alcohol and cyclohexanol

Front 15

why is phenol more acidic?

Back 15

1. delocalization of conjugate base adds extra stability
2. sp2 is more electron withdrawing than sp3

Front 16

what increases the acidity of a phenol?

Back 16

1. adding a more electron withdrawing group as a substituent
2. location of substituent: ortho/para positions cause more acidity than meta

Front 17

WIlliamson Ether Synthesis

Back 17

1. conjugate base of phenol used to create ethers
2.

Front 18

ubiquinone

Back 18

1. phenol used throughout the electron transport chain
2. consists of quinine rings connected to isoprene

Front 19

BHT

Back 19

1. radical formed from BHT does not propagate (steric hinderance)
2. BHT used to slow down radical ractions

Front 20

What happends when HBr reacts with phenolic ester

Back 20

1. simple phenol bound to OH
2. alkane bromide
3. no Sn2 sub

Front 21

What happens when HBr reacts with 2 connected benzene rings?

Back 21

1. no reaction

Front 22

Stille Reaction

Back 22

1. used to couple C-C bonds between phenols and tin containing carbon compounds
2. good for connecting alkyl groups to benzene rings

Front 23

carbonyl group

Back 23

1. contains aldehydes and ketons
2. C=O

Front 24

aldehyde

Back 24

carbonyl group at end of C chain

Front 25

ketone

Back 25

carbonyl group within C chain

Front 26

formaldehyde

Back 26

1. C=O between 2 hydrogens
2. H-(C=O)-H
3. aldehyde

Front 27

propionaldehyde

Back 27

1. H-(C=O)-C-C-C
2. aldehyde

Front 28

acetophenone

Back 28

1. Ph-(C=O)-CH3
2. ketone

Front 29

benzophenone

Back 29

1. Ph-(C=O)-Ph
2. ketone

Front 30

acetone

Back 30

1. H3C-(C=O)-CH3
2. ketone

Front 31

methyl ethyl ketone

Back 31

1. H3C-(C=O)-CH2CH3

Front 32

formyl

Back 32

R-(CO)H

Front 33

acyl (Ac-)

Back 33

R-(C=O)-CH3

Front 34

Benzoyl (Bz-)

Back 34

R-(C=O)-Ph

Front 35

suffix for an aldehyde

Back 35

-anal

Front 36

suffix if there are two aldehydes

Back 36

1. dial

Front 37

suffix if aldehyde is on a ring

Back 37

carbaldehyde

Front 38

suffix for ketone

Back 38

-one

Front 39

at what peak does carbonyl group show up on IR?

Back 39

approx 1700cm-1

Front 40

IR uncojugated ketone?

Back 40

1710-1715

Front 41

IR unconjugated aldehyde?

Back 41

1720-1725

Front 42

conjugated aldehyde

Back 42

1685

Front 43

IR of strained rings

Back 43

1. peak at greater frequencies
2. the more strained, the greater the frequency of peak