CHAPTER 12. Substituted Benzene
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1 CHAPTER 12 Substituted Benzene 12.1 Alkylbenzenes (Ar-R) Bezylic carbons: CH 3 CH 2 CH 3 CH(CH 3 ) 2 1
2 Reactions of Alkylbenzens 1. Free Radical Halogenation CH 2 CH 3 Br 2 hv Br CHCH 3 2
3 2- xidation R KMn 4 hot C 2 H CH 3 KMn4 hot C 2 H CH 2 CH 3 Mn - 4 hot C 2 H CH 2 CH 3 CHCH 3 Mn - 4 hot C 2 H 3
4 Notice: CH 3 CCH 3 CH 3 Mn - 4 hot No Reaction Benzylic carbon has no hydrogen CH 3 CH 3 Mn - 4 hot H 2 C C 2 H - Mn 4 hot C 2 H C 2 H 4
5 Phenols (Ar) A phenol has a hydroxyl group directly attached to the benzene ring SP 2 - hybridized carbon C--- bond is not easily broken No substitution or elimination reaction R- HBr RBr H 2 S N 1 or S N 2 5 Ar- HBr No reaction
6 Acidity of Phenols CH 3 CH 2 Na CH 3 CH 2 - Na H 2 Not favored pka= 16 pka=15.7 Na - Na H 2 favored pka= 10 pka= R X SN 2 R X - 6 a phenoxide ion
7 Esterfication of phenols CH 3C CCH 3 CCH 3 CH 3 C 2 H 7
8 The Kolbe Reaction 1) - 2) C 2 3) H Mechanism C 2 H - - δ δ- C H C - 8 Salicylic acid C 2 H H C 2 -
9 Importance of Kolbe Reaction To Synthesize aspirin C 2 H CH 3 CCCH 3 CCH 3 C 2 H Acetylsalicylic acid (Aspirin) 9
10 The Reimer-Tiemann Reaction The reaction of phenol with chloroform in the presence of base. 10 1) CH 3, -, ο 70 C 2) H 2, H CH Salicylaldehyde
11 Mechanism: - H C 3 - H 2 H.. C2 - C 2 C 3 - C 2 dichlorocarbene CH H H H H CH
12 xidation of phenols: phenol resists oxidation xidation of hydroquinones (1,4-dimethoxy benzenes) 2 H 2e - H hydroquinone 1.4-benzoquinone H (quinone) 2 H 2e benzoquinone 12
13 Preparation of Aniline HN 3 H 2 S 4 Fe, H N H NH 2 H 2, Pd/C or Pt 13
14 Benzenediazonium Salts Na, H, 0 C NH N N - 2 H 2 benzenediazonium chloride very reactive Excellent leaving abilty of N 2 gas _ N2 N N Nu - Nu 14
15 Reactions of benzenediazinium Salts Br CN 1) HN 3, H 2 S 4 2) H 2, Pt Cu CuBr CuCN, KCN Na,H, NH 2 0 C N N - KI I H 3 P 2 H H 2, H 1)HBF 4 2) heat F 15
16 Coupling reactions N N N N N N N N C 2 H Azo compound NH 2 Na, H, 0 C 16 C 2 H N N NHCH 3 N N NHCH 3
17 Synthesis involving diazonium salts CH 3???? CH 3 C N HN 3, H 2 S 4 CuCN, KCN CH 3 1) Fe,H 2) - CH 3 N 2 - Na, CH 3 NH 2 H, C 17
18 Nucleophilic Aromatic Substitution X Nu - No SN1 or SN2 reaction But X Nu - Nu X- Nucleophilic Aromatic Substitution 18
19 Examples 10% Na o atm Increasing Nucleophicty towards Nu: - 2 N 10% Na 160 o 2 N P-nitrophenol 2 N H 2 warm 2 N 19
20 ther nucleophiles NH 3 2 N heat 2 N NH 2 CH 3 CH 2 S - 2 N heat 2 N SCH 2 CH 3 20
21 Carbanion Mechanism: If the ring is activated toward nucleophilc substitution by an electron withdrawing group (I,e ) Two steps 1) addition of Nu: to form carbanion 2) Loss of the halide ion - 2 N slow 2 N - fast 2 N Carbanion intermediate 21
22 Carbanion intermediate is stabilized by resonance - - N 2 N N - N - 22
23 Benzyne Mechanism: If there is no electron withdrawing substituent on the ring. Mechanism NH 2 -, NH 3 NH 2 - H NH 2 - NH 2 H NH 2 - Benzyne NH 3 23 NH 2 - NH 2
24 Benzyne H H H H 24
25 Syntheses of substituted benzene compounds How would you synthesize HN 3 2 H 2 S 4 N2 Fe 3 But IF YU START WITH CHLRINATIN 2 Fe 3 HN 3 H 2 S 4 o,p-director 25
26 Syntheses??? Br NH 2 HN 3 H 2 S 4 Br 2, FeBr 3 1) Fe, H 2) - Br 26
27 Note: Nitro group can be converted to arylamines which in turn can also be converted to aryldiazonium salts,=> making a diversity of substituted products 1) Fe, H 2) - m-director NH 2 o,p-director Na, H 0o Nu N 2 easily displaced Nu Notice: Amino group does not undergo Friedel-Crafts reaction because an amino group reacts with Lewis acid since it is basic to form strongly deactivating grouo 27 NH 2 Al 3 N H 2 Al - 3 strongly deactivating
28 Nitrobenzene does not undergo Friedel-Crafts reactions RX or RCX AlX 3 No aromatic substitution Notice: An amino group is o,p-director, but an ammonium group ( -NR 3 ) is an m-director and deactivating. NH 2 HN 3 N H 3 N - 3 o,p-director m-director 28
29 Sulfonic acid group (-S 3 H) The sulfonic acid group is easily removed and can be displaced by a variety of reagents. S 3 H H 2, H H 2 S 4 S 3 H 1) Fused Na 2) H 2, H 29
30 ??? Br Br 2, FeBr 3 H 2, H Br HN 3 H 2 S 4 Br 1) Fe, H Br NH 2 2) - Na,H Br N 2 0 o 30
31 ??? Br Br HN 3 H 2 S 4 CuBr Br 2, FeBr 3 Br Br 1) Fe, H 2) - NH 2 Na,H 0 Br N 2 31
32 ???? CH 3 C 2 H KMno 4, heat 2, Fe 3 C 2 H 32
33 ???? C 2 H CH 3 CH 2, Al 3 CH 2 CH 3 NH 2 KMn 4 heat HN 3, H 2 S 4 CH 2 CH 3 1) Fe, H 2) - CH 2 CH 3 NH 2 33
34 ???? CH 3 HN 3, H 2 S 4 CH 3 I - H 2,Pd/C NH 2 1) Na,H 2) H 2, H Na 34
35 ???? CH 3 CH 3 HN 3, H 2 S 4 H 3 P 2 2 N CH 3 H 2 N H 2,Pd/C 1) 2,Fe 3 - N 2 CH 3 2) Na, H CH 3 35
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