Aromaticity Reagents

Question 1

Answer 1

Question 2

Answer 2

Question 3

Answer 3

Question 4

Answer 4

Question 5

Answer 5

Question 6

Answer 6

Question 7

Answer 7

Reduction of Nitro Groups

Question 8

Answer 8

Oxidation of side chain

Question 9

Answer 9

Halogenation of side chain

Question 10

Answer 10

Reduction of ketone to alkane

Question 11

Answer 11

Conversion of ketone to ester

Question 12

Answer 12

Electrophilic Aromatic Substitution Mechanism
1. pi bond attack E+
2. H removal regenerates aromaticity

Question 13

What makes an Activating group on a ring favor the ortho and para positions for EAS to occur there?

Answer 13

The activating group is able to donate electron density to the carbon it’s attached to, giving it the ability to help stabilize the positive charge better (extra stability)

Question 14

What makes a Deactivating group on a ring favor the meta position for EAS to occur there?

Answer 14

The deactivating group is able to pull some of that electron density away from the carbon it’s attached to, giving it the ability to help stabilize the negative charge better (extra stability)

Question 15

Answer 15

Para generally favored due to steric hinderance

Question 16

Answer 16

Strong Activator
o-
p-

Question 17

Answer 17

Strong Activator
o-
p-

Question 18

Answer 18

Strong Activator
o-
p-

Question 19

Answer 19

Strong Activator
o-
p-

Question 20

Answer 20

Strong Activator
o-
p-

Question 21

Answer 21

Moderate Activator
o-
p-

Question 22

Answer 22

Moderate Activator
o-
p-

Question 23

Answer 23

Moderate Activator
o-
p-

Question 24

Answer 24

Moderate Activator
o-
p-

Question 25

Answer 25

Weak Activator
o-
p-

Question 26

Answer 26

Weak Deactivator
o-
p-

Question 27

Answer 27

Moderate Deactivators
m-

Question 28

Answer 28

Moderate Deactivators
m-

Question 29

Answer 29

Moderate Deactivators
m-

Question 30

Answer 30

Moderate Deactivators
m-

Question 31

Answer 31

Moderate Deactivators
m-

Question 32

Answer 32

Moderate Deactivators
m-

Question 33

Answer 33

Moderate Deactivators
m-

Question 34

Answer 34

Strong Deactivators
m-

Question 35

Answer 35

Strong Deactivators
m-

Question 36

Answer 36

Strong Deactivators
m-

Question 37

Answer 37

not aromatic (antiaromatic)

Question 38

Answer 38

aromatic

Question 39

Answer 39

not aromatic (antiaromatic)

Question 40

Answer 40

aromatic

Question 41

Answer 41

aromatic

Question 42

Answer 42

aromatic

Question 43

Answer 43

aromatic

Question 44

Answer 44

aromatic

Question 45

Answer 45

aromatic

Question 46

Answer 46

aromatic

Question 47

Answer 47

not aromatic

Question 48

Answer 48

aromatic

Question 49

Answer 49

aromatic

Question 50

Answer 50

aromatic

Question 51

Answer 51

aromatic

Question 52

4 rules to Aromaticity

Answer 52

1. Must be a ring
2. Must be conjugated (a continuous line of p orbitals around the ring/p orbitals can come from π-bonds, lone pairs, or carbocations)
3. Must be 4n + 2 pi electrons
4. Must be planar/flat

Question 53

“Frost circles” - a trick for obtaining the molecular orbital structures of aromatic rings
- Inscribe a polygon of n sides in a circle. Make sure one of the apices is pointing _________. Then, each apex will represent a level in the molecular orbital energy diagram

Answer 53

down

Question 54

Answer 54

Hydrogenation of Benzene
- reduction

Question 55

Answer 55

Birch Reduction

Question 56

Answer 56

Birch Reduction with electron donating substituent

Question 57

Answer 57

Birch Reduction with electron withdrawing substituent