Flashcards in Chapter 19 Deck (50):
1
electrophilic aromatic substitution
aromatic proton is replaced by electrophile
adding iron to reaction, causing the addition of halide
2
Halogenation
feBr3 reacts with Br2 to form complex that acts as Br+
aromatic ring is nucleophile and attacks electrophile to prodice sigma complex
3
Halogentation - product
produces aromatic ring with addition of a halide
4
Halogenation - reagants
FeBr3
Br2
or
ALBr3
Br2
5
Sulfonation - reagants
fuming H2sO4
6
sulfonation - products
aromatic ring + SO3H
7
sulfonation - concentrated fuming H2SO4
creates aromatic ring + SO3H
8
Sulfonation - dilute H2SO4
goes from aromatic ring + SO3H to benzene
9
Nitration - reagants
HNO3
H2SO4
10
Nitration - products
produces aromatic ring with NO2
11
To produce amino
once NO2 is added to ring, can be reacted to form NH2
12
To produce amino - reagants
Fe or Zn
HCl
13
Friedel craft akylation - reagants
halogenated akyl halide
AlCl3
14
Friedel craft akylation - carbocation structure
cant use primary, they will undergo rearrangement to form secondary or tertiary
15
Friedel craft akylation - products
addition of carbon chain on benzene
16
Friedel craft akylation - efficiency
can use substrates that undergo rearrangement
17
Friedel craft akylation - alkyl halide used
carbon connected to the halogen must be sp3
vinyl and aryl carbocations arent stable to form under friedels craft
18
Friedel craft akylation - installation of alkyl
activates ring to further alkylation
polyalkyations usually occurs
19
Friedel craft akylation - uncompatable groups
certain groups like nitros are incompatable
20
Friedel craft acylation - product
benzene with R group
R-C=O(Cl) group
aryl ketone
21
Friedel craft acylation - reagants
R-C=O(Cl) group
AlCl3
22
acylium ion
formed from removal of leaving group of R group
resonance stable and doesnt undergo rearrangement
23
Clemmensen reduction - product
reduces ketone to carbon chain
24
Clemmensen reduction - reagants
Zn(Hg)
HCl
Heat
25
Methyl group - activating
activates ring
26
Activating groups - position of the added
ortho para, usually para to stop steric hindarance
27
Deactivating groups - position of added
meta
28
Activating groups
donates electron density to the ring
usually have electronegative negative atom
makes ring positive
29
Deactivating groups
withdraws electron density from ring
usually electronegative positive atoms
makes ring negative
30
Halogens - the exception
are ortho para even though they are deactivators
31
Strong activators
presence of lone pair adjacent from ring
with electronegative atoms
lone pair delocalises into the ring
32
Moderate Activators
have lone pair delocalised outside ring
lone pair next to ring, nut lone part participates in resonance outside ring
33
Weak activators
donate electron density by weak effect of hyperconjugation
akyl groups
34
Weak Deactivators
halogens
35
Moderate deactivators
pi bond to electronegative atom
carboxylic acids
aldehydes
36
Strong deactivators
NO2
N-R3+
C-X3
37
Directing effect
each substituents have to be placed specifically
38
Directing effect - competition
more powerful activating group dominates
39
Blocking Groups
installed in order to block the position needed
40
Blocking group - properties
must be easily removable
sulfonation is generally used as its reversible
41
Nitration - limitation
cant be performed on ring with amino group
42
Friedels craft reaction - limitation
can be accomplished on rings with moderate or strong deactivators
must be activated or weak deactivator
43
Nucleophilic Aromatic Substitution
aromatic compound is treated with strong nucleophile which displaces leaving group
44
Nucleophilic Aromatic Substitution - reagants
NaOH 70 degrees
H30+
45
Nucleophilic Aromatic Substitution - criteria
ring must have powerful deactivator
must have leaving group
leaving group must be ortho or para to deactivator
46
Elimination - Addition - products
produces benzene ring with new
compound
47
Elimination addition - reagants
NaOH
H3O+
Heat
48
Elimination addition - reagants - low temps
NaNH2 NH3(l)
H3O+
49
Bromination
adds bromine
50