lecture 8

Question 1

toluene to saccharin needs

Answer 1

activated chlorosulfonic acid
ammonia
KMnO4
HCl

Question 2

steps for toluene to saccharin

Answer 2

toluene + chlorosulfonic acid (activates inself by removing a H2O )

the S is attacked by NH3 and the Cl is kicked off

KMnO4 oxidised the CH3 into COOH

HCl is aded for the NH2 to attack the COOH (HCl added a H) and kick off the water

H is removed from the N to make it stable. this is an intramolecular substitution reaction

Question 3

I and F,, which is more ORTHO directing

Answer 3

I 45%

F 13% (more EW)

Question 4

I and F,, which is more PARA directing

Answer 4

F 86%
I 54%

F is more extreme
low ortho,, higher para

Fate = high parasailing

Question 5

fluoro benzene and its deactivating abilities

Answer 5

slows down nitration rate,, the F has a + charge and can stabilise it

its ortho and para directing

Question 6

where is the directing based off

Answer 6

its based off where the substituent is

not where the other one is

Question 7

if 2 substituents direct a group to 2 different substituents,, which one has priority

Answer 7

the one with the lone pair has the higher directing priority

the electrophile is directed where the highest directing substituent goes.

Question 8

with a combo of different directing options,, what else effects where the group is added

Answer 8

steric hinderence

if the para position is inbetween 2 different substituents the groups being added will go to the other option

Question 9

what to look out for when adding stuff

Answer 9

• directing power
• steric hinderence

Question 10

p-cresol

Answer 10

phenol with CH3 in the para position

Question 11

when smt is added in electophilic addition what happens

Answer 11

double bond breaks and attacks electrophile

electophile bonds

h is removed in order to regenerate aromaticity (this normally happens by itself)

Question 12

turning NO2 substituent into NH2

Answer 12

H2 and Pd

reduction