benzene substituents Flashcards

1
Q

when do we use NBS

A

when we want monosubstitution of Br onto the benzylic carbon

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

what is NCS

A

NBS with Cl instead of Br

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

what is the best way to put a halogen onto the benzylic carbon of a benzene

A

use NBS or NCS

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

what happens if we react benzyl halides with a strong nucleophile

A

Sn2 = inversion of chemistry

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

what happens if we do Sn1 on a benzyl halide

A

we get a racemic mix

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

what do we get when benzylic carbons are oxidized

A

benzoic acids (R –> carboxylic acid group)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

what can we use to oxidize

A

Jones, KMnO4

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

for oxidation of benzylic carbons, what needs to be on the molecule for the reaction to occur

A

we need benzylic hydrogens

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

what happens if we use a MILD oxidizing agent on a benzylic carbon

A

we get a ketone or aldehyde

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

how do we get a carboxylic acid from a benzylic carbon

A

oxidation with a strong ox agent

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

how do we get a ketone from a benzylic carbon

A

mild oxidation of a toluene

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

how do we get an aldehyde from a benzylic carbon

A

mild oxidation of anything other than a toluene

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

what do we use to do selective oxidation (ie leaving a terminal OH group alone but reacting a dif. OH group)

A

we use MnO2 to be selective. OH turns into a ketone, and terminal OH stays the same

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

what two reactions can we do with benzyl ethers

A

reduction or oxidation

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

what do we get by reducing a benzyl ether

A

toluene

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

what do we use to reduce benzyl ethers

17
Q

what do we get by oxidizing a benzyl ether

A

benzoic acid

18
Q

what do we use to oxidize benzyl ethers

A

KMnO4 or Jones

19
Q

how might we produce benzoic acid from a basic benzene ring

A

pressurize it using CO2

ie use CO2, KHCO3(aq), with pressure

20
Q

how do we convert nitrobenzene (strong deactivator) to aniline (strong activator)

A

reduction

  • clemmensen (Zn, Hg, HCl)
  • H2 Pd/C, or Adams, or Raney Ni
21
Q

how do we make an aryl cation

A

oxidize aniline to get an Arenediazonium salt, and then heat it to get the aryl cation

22
Q

why are arenediazonium salts so useful

A

they’re the precursors of many products

23
Q

in what position will the sub be added when it reacts with an arenediazonium salt

24
Q

what happens when we react an azenediazonium salt with another benzene

A

forms azo compounds: compounds joined by N=N double bond

25
are phenols acidic or basic
acidic
26
how do we make phenol
oxidize aniline and then put it in heated water
27
T or F: phenol is a good nucleophile
true
28
why is phenol a good nucleophile
deprotonation of the OH group makes it a good nucleophile
29
how can we change the pKa of phenol
by adding substituents onto the ring that change the electron density
30
what sub is on the ring for alkoxybenzenes
OR
31
how do we make alkoxybenzene
react phenol with NaOH to make it a nuc, and then with RX to add the R
32
T or F: the production of alkoxybenzene is concerted
true
33
how do we make a benzene with an ester attached
react phenol with NaOH to make it a good nuc, then with RCOX to make the ester