Exam 1

Front 1

-NH2

Back 1

strongly activating, o/p

Front 2

-NHR

Back 2

strongly activating, o/p

Front 3

-NR2

Back 3

strongly activating, o/p

Front 4

-OH

Back 4

strongly activating, o/p

Front 5

-OR

Back 5

strongly activating, o/p

Front 6

-NHCOR

Back 6

moderately activating, o/p

Front 7

-ROOC

Back 7

moderately activating, o/p

Front 8

-R

Back 8

weakly activating, o/p

Front 9

-Ar

Back 9

weakly activating, o/p

Front 10

-CHCHR

Back 10

weakly activating, o/p

Front 11

-F

Back 11

weakly deactivating, o/p

Front 12

-Cl

Back 12

weakly deactivating, o/p

Front 13

-Br

Back 13

weakly deactivating, o/p

Front 14

-I

Back 14

weakly deactivating, o/p

Front 15

-COH

Back 15

moderately deactivating, m

Front 16

-ROC

Back 16

moderately deactivating, m

Front 17

-COOH

Back 17

moderately deactivating, m

Front 18

-OCCl

Back 18

moderately deactivating, m

Front 19

-CN

Back 19

strongly deactivating, m

Front 20

-SO3H

Back 20

strongly deactivating, m

Front 21

+NH2R

Back 21

strongly deactivating, m

Front 22

+NR3

Back 22

strongly deactivating, m

Front 23

-NO2

Back 23

strongly deactivating, m

Front 24

+NH3

Back 24

strongly deactivating, m

Front 25

+NHR2

Back 25

strongly deactivating, m

Front 26

benzene + CH3

Back 26

toluene

Front 27

benzene + OH

Back 27

phenol

Front 28

benzene + OCH3

Back 28

anisole

Front 29

benzene + NH3

Back 29

aniline

Front 30

benzene + COOH

Back 30

benzoic acid

Front 31

benzene + COH

Back 31

benzaldehyde

Front 32

Benzene + COCH3

Back 32

acetophenone

Front 33

benzene + CHCH2

Back 33

styrene

Front 34

ortho

Back 34

1,2 position

Front 35

meta

Back 35

1,3 position

Front 36

para

Back 36

1,4 position

Front 37

Electron Donating Group

Back 37

Activating group, destabilizes the intermediate of the observed product

Front 38

Electron Withdrawing Group

Back 38

Stabilizes the intermediate, deactivating group

Front 39

Electrophilic Aromatic Substitution

Back 39

Weak nucleophile becomes strong electrophile. Benzene ring acts as nucleophile

Front 40

conjugated dienes

Back 40

formed by elimination reactions using a strong bulky base

Front 41

1,2 adduct

Back 41

formed faster, favored at low temperatures

Front 42

1,4 adduct

Back 42

more stable because more substituted, works at high temperatures

Front 43

Diels Alder Reactions

Back 43

- favored at low and moderate temperatures (below 200 C)

- favored when the enthalpy term is larger than the entropy term (exothermic)

Front 44

Dienophile in Diels Alder Reactions

Back 44

- mechanism not favored when dienophile is not substituted with an electron withdrawing group

- reaction is spontaneous when electron withdrawing group is attached to dienophile

Front 45

Diels Alder Reactions: EWG

Back 45

- directly attached to the double bond

- have a pi bond to an electronegative atom

- aldehydes, ketones, carboxylic acids

Front 46

Stereoselectivity of Diels Alder Reactions

Back 46

Either E or Z depending on conformation of dienophile

- Exception: 8 carbons or less is always Z

Front 47

Endo Preference

Back 47

- when cyclic compounds are used as dienes, product is favored when substituents are syn to the larger bridge

- closer to pi bond, more favorable interaction with EWG on diene and new pi bond

- transition state is lower in energy

Front 48

The Diene in Diels Alder Reactions

Back 48

can only proceed with the diene adopts an s-cis conformation

- more reactive than s-trans