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Organic Chemistry > Chapter 19 > Flashcards

Chapter 19 Flashcards

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1
Q

electrophilic aromatic substitution

A

aromatic proton is replaced by electrophile

adding iron to reaction, causing the addition of halide

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2
Q

Halogenation

A

feBr3 reacts with Br2 to form complex that acts as Br+

aromatic ring is nucleophile and attacks electrophile to prodice sigma complex

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3
Q

Halogentation - product

A

produces aromatic ring with addition of a halide

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4
Q

Halogenation - reagants

A 
FeBr3
Br2 
or 
ALBr3
Br2
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5
Q

Sulfonation - reagants

A

fuming H2sO4

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6
Q

sulfonation - products

A

aromatic ring + SO3H

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7
Q

sulfonation - concentrated fuming H2SO4

A

creates aromatic ring + SO3H

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8
Q

Sulfonation - dilute H2SO4

A

goes from aromatic ring + SO3H to benzene

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9
Q

Nitration - reagants

A

HNO3

H2SO4

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10
Q

Nitration - products

A

produces aromatic ring with NO2

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11
Q

To produce amino

A

once NO2 is added to ring, can be reacted to form NH2

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12
Q

To produce amino - reagants

A

Fe or Zn

HCl

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13
Q

Friedel craft akylation - reagants

A

halogenated akyl halide

AlCl3

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14
Q

Friedel craft akylation - carbocation structure

A

cant use primary, they will undergo rearrangement to form secondary or tertiary

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15
Q

Friedel craft akylation - products

A

addition of carbon chain on benzene

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16
Q

Friedel craft akylation - efficiency

A

can use substrates that undergo rearrangement

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17
Q

Friedel craft akylation - alkyl halide used

A

carbon connected to the halogen must be sp3

vinyl and aryl carbocations arent stable to form under friedels craft

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18
Q

Friedel craft akylation - installation of alkyl

A

activates ring to further alkylation

polyalkyations usually occurs

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19
Q

Friedel craft akylation - uncompatable groups

A

certain groups like nitros are incompatable

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20
Q

Friedel craft acylation - product

A

benzene with R group
R-C=O(Cl) group
aryl ketone

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21
Q

Friedel craft acylation - reagants

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A

R-C=O(Cl) group

AlCl3

22
Q

acylium ion

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A

formed from removal of leaving group of R group

resonance stable and doesnt undergo rearrangement

23
Q

Clemmensen reduction - product

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A

reduces ketone to carbon chain

24
Q

Clemmensen reduction - reagants

Study These Flashcards
A

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
Bromination reagents
NBS | CCl4

Organic Chemistry (7 decks)

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