CH 18 Rxns

Question 1

In EAS, what acts as the nuc

Answer 1

benzene

Question 2

what is the intermediate called in an EAS

Answer 2

arenium ion, sigma complex, cyclohexadienyl cation

Question 3

In EAS, which step is the RDS

Answer 3

first step: addition of electrophile to the benzene ring

Question 4

Reagents for bromination of benzene

Answer 4

Br2, FeBr3

Question 5

Reagents for chlorination of benzene

Answer 5

Cl2, AlCl3

Question 6

Reagents for iodination of benzene

Answer 6

I2, HNO3/CuCl2

Question 7

Reagents for sulfonation (H–> SO3H)

Answer 7

SO3, H2SO4, heat
or
H2SO4, heat

Question 8

Reagents for desulfonation (SO3H –> H)

Answer 8

H2SO4, H20

Question 9

Reagents for nitration of benzene

Answer 9

HNO3, H2SO4

Question 10

Reduction of nitro group to amine

Answer 10

H2
Ni, MeOH
or
1)Fe/Zn/Sn ,HCl
2)NaOH

Question 11

FC Alkylation reagents

Answer 11

Secondary or tertiary alkyl halide, AlX3

Question 12

what are the 4 limitations to FC limitations

Answer 12

1. only alkyl halides can react. need the carbocat. intermediate
2. over-alkylation can occur bc adding alkyl groups makes benzene more nuc
3. Substrate can’t have strong EWG bc it deactivates the benzene too much
4. Anilines don’t undergo FC alkylation or acylation bc the N binds to the Al

Question 13

what do u need to protect NH2 with if want to do FC?

Answer 13

Acyl chloride, pr

Question 14

Reagents for FC acylation

Answer 14

Acyl chloride, AlCl3

Question 15

acyl chlorides are prepared from carboxylic acids using what? (replaces OH with Cl)

Answer 15

thionyl chloride (SOCl2)

Question 16

Clemmenson reduction reagents

Answer 16

Zn(Hg), HCl, heat

Question 17

what env does the clemmenson reduction occur in

Answer 17

acidic

Question 18

Wolff Kishner reduction reagents

Answer 18

NH2NH2, KOH, heat

Question 19

what env does Wolff Kishner reduction occur in

Answer 19

basic

Question 20

what is the intermediate called for the wolff-kishner reduction

Answer 20

hydrazone

Question 21

alkyl groups are?

Answer 21

weak activating, O/P

Question 22

amine groups are?

Answer 22

strong activator, O/P

Question 23

alcohols are ?

Answer 23

strong activator, O/P

Question 24

“esters” are? (-OC=OR)

Answer 24

moderate activator, O/P

Question 25

amides are? (-NHC=OR)

Answer 25

moderate activators, O/P

Question 26

alkoxy groups are? (-OR)

Answer 26

moderate activators, O/P

Question 27

alkyl groups are?

Answer 27

weak activators, O/P

Question 28

Halides are?

Answer 28

weak deactivators, O/P

Question 29

O=C-R

Answer 29

moderate deactivator, meta

Question 30

O=CH

Answer 30

moderate deactivator, meta

Question 31

O=C-OR

Answer 31

moderate deactivator, meta

Question 32

O=C-OH

Answer 32

moderate deactivator, meta

Question 33

O=C-NH2

Answer 33

moderate deactivator, meta

Question 34

-SO3H

Answer 34

moderate deactivator, meta

Question 35

-CN

Answer 35

moderate deactivator, meta

Question 36

NO2

Answer 36

strong deactivator, meta

Question 37

NR3+

Answer 37

strong deactivator, meta

Question 38

CX3

Answer 38

strong deactivator, meta

Question 39

What to use to protect NH2 in order to do FCA

Answer 39

acetic anhydride, acyl chloride with pyr

Question 40

what to use to deprotect NH2 after doing FCA

Answer 40

KOH, H20

Question 41

Characteristics of a SNAR rxn

Answer 41

LG (halide) and EWG (NO2) that is O/P to LG, attacked by nuc like -OMe

Question 42

characteristics of a EAS rxn

Answer 42

benzene acts as nuc and attacks e-phile

Question 43

what groups cannot be on benzene if want to do FCA

Answer 43

NO2, CN, SO3H
ketones, aldehydes, COOH, amides

Question 44

reagents to convert CH3 to CX3

Answer 44

xs NBS, heat