Flashcards in Chapter 18 Deck (23):
1
Huckels rule
odd number of pi electrons pairs
4n + 2
2
Criteria for aromaticity
must contain ring of continuous overlapping p orbitals
4n+2
3
Antiaromatic
fully conjugated
4n electrons
4
benzylic position
carbon attached to benzyllic position
5
Oxidation of alkylbenzene - reagents
Na2CrO4
H2SO4
H2O
6
oxidation of benzene
wont occur
7
oxidation of alkyl benzene
oxidation occurs at benzylic position
produces carboxylic acid
cuts off rest of alkyl chain after benzyl position
must have 1 hydrogen
8
Oxidation of alkylbenzene - other reagants
KMnO4
H2O
Heat
9
Free Radical bromination
occurs at benzyl position
addition of 1 bromine
10
Free Radical Bromination - reagants
NBS
Heat
11
Susbtitution Reactions of benzyl halides
undergo SN1 reactions rapidly
addition of OH
will undergo SN2 if not sterically hindered
12
Susbtitution Reactions of benzyl halides - reagants
H2O
13
Elimination of benzyl halides
undergo either E1 or E2
14
Elimination of benzyl halides - reagants -E1
conc H2SO4
15
Elimination of benzyl halides - reagants - E2
NaOEt
16
Hydrogenation of benzene
produces cyclohexane
with 3 equivalent of H2
17
Hydrogenation of benzene - reagants
Ni
100 atm
150 degrees
18
Hydrogenation of vinyl group in benzene - reagants
H2
Pt
2am
25 degrees
19
Birch reduction of benzene - reagents
na
CH3OH
NH3
20
Birch reduction of benzene
similar to dissolving metal reduction
produces 1,4 cyclohexadiene
reduced carbons are opposite each other
21
Birch reduction of benzene - mechanism
nucleophilic attack
proton transfer
Nucleophillic attack
proton transfer
22
Birch reduction of alkyl benzene - electron donating group
carbon attached to alkyl group isnt reduced
23