17

Question 1

Ways to single addition to a benzene ring

Answer 1

Br2+–FeBr3->FeBr4–>Bromobenzene

Question 2

Br2+FeBr3=

Answer 2

FeBr4-

Question 3

Chlorination of Benzene catalyst

Answer 3

Cl2+AlCl3

Question 4

Iodination of Benzene requires

Answer 4

HNO3 to form I+ which will attach to the benzene

Question 5

Nitration of benzene uses

Answer 5

HNO3 with H2SO4 as a catalyst

Question 6

HNO3 with H2SO4 forms

Answer 6

Nitronium ion which can attach to a benzene to form nitrobenzene

Question 7

Nitrated benzene + ___ in ___ forms an ____ group

Answer 7

Zn/Sn/Fe in HCl

forms an Amine group

Question 8

Sulfonation reagents

Answer 8

SO3 (sulfur trioxide added)

H2SO4 (not a catalyst, adds proton to SO3 group attached)

Question 9

Benzene+Sulfer trioxide in H2SO4

Answer 9

Intermediate: Benzenesulfonate anion
Product: Benzenesulfonic acid

Question 10

Sulfonation is reversible by

Answer 10

heating in dilute sulfuric acid

Question 11

Desulfonation will/will not win out over time and reversing of reaction

Answer 11

will, SO3 will be consumed

Question 12

pTsOH

Answer 12

H3C-Benzene-Sulfonic acid

Question 13

Toluene reacts faster/slower than benzene

Answer 13

25 times faster

Question 14

Nitration of the toluene produces

Answer 14

mostly o-nitrotoluine with some p-nitrotoluene and barely any m-nitrotoluene

Question 15

Reason why meta attack of nitro on toluene doesn’t work well:

Answer 15

can’t form a tertiary carbocation. The plus prefers the three sigma bonds in the sigma complex.

Question 16

Ortho and para have lower activation energy than meta with sigma complex’s because

Answer 16

meta has higher energy resonance

Question 17

Benzene serves as the ___ in eas reactions

Answer 17

nucleophile

Question 18

The sigma complex is the _____ ______ and the highest/lowest energy point

Answer 18

reactive intermediate

highest

Question 19

Toluene’s methyl group is a/an _____

Answer 19

activator

Question 20

activating groups are ____ directing

Answer 20

o/p

Question 21

Para becomes bigger when

Answer 21

steric group gets bulky. Less room.

Question 22

Aniline rings and BR

Answer 22

Aniline is so activated that you don’t need a catalyst.

Question 23

Activators generally have

Answer 23

lone pairs

Question 24

Deactivating groups are more/less reactive than benzene

Answer 24

less

Question 25

Electron withdrawers are

Answer 25

deactivating groups. They pull electrons from the ring.

Question 26

most deactivators are

Answer 26

meta directing

Question 27

nitro groups are

Answer 27

100,000 times slower than benzene (93% meta)

Question 28

deactivators have a plus size adjacent to the ortho and para plus, which makes them less stable

Answer 28

ye

Question 29

Benzene in high heat, high pressure, and a metal like platinum/nickel Ru or Rh

Answer 29

Breaks aromaticity and yields 100% cyclohexane

Question 30

Birch reduction reagents and products

Answer 30

Na or Li
in Ammonia and ROH

yield 90% anti aromatic ring with two double bonds.

Question 31

I’m Birch reaction the two carbons that get reduced have to

Answer 31

hold extra electrons, so carbons with electron withdrawing groups stabilize middle steps. Donor group carbons won’t take extra electron since it is less stable

Question 32

In the birch reduction, a carbon bearing an electron-withdrawing carbonyl group is not/is reduced

Answer 32

is

Question 33

In the birch reduction, a carbon bearing an electron-releasing alkoxy group is not/is reduced

Answer 33

is not

Question 34

reduction increases

Answer 34

H-C bonds

Question 35

Oxidation increases

Answer 35

C-O bonds

Question 36

During side chain oxidation

Answer 36

benzenes and first carbon of chain survive. Rest is replaced with the -O

Question 37

Side chain oxidation only works with carbon groups?

Answer 37

yes, nitro groups won’t oxidize.

Question 38

KMnO4 can oxidize side chains due

Answer 38

to d-orbital chemistry.

Question 39

A benzylic position is

Answer 39

an electron that is in the p orbital and stabilized by the benzene’s aromaticity.

Question 40

When you want Bromine, use NBS or Br2 in __

Answer 40

NBSS is better

hv

Question 41

Phenols are acidic-basic

Answer 41

acidic (more acidic than water

Question 42

The C-O bond is stronger/weaker than the O-H bond in phenol

Answer 42

stronger

Question 43

oxidizing a phenol yield

Answer 43

diketone (quinone)

Question 44

Phenols are what directing

Answer 44

orho para