Chapter 18 Flashcards Preview

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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

Birch reduction of alkyl benzene - electron withdrawing group

carbon attached to alkyl group is reduced
carbon is electron withdrawing via resonance