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C 6 H 6

Benzene Reaction Chart. C 6 H 5 CH 2 CH 3. Sulphonic acid C 6 H 5 SO 3 H. Zn/Hg c. HCl. C 6 H 5 COCH 3. Conc. H 2 SO 4. 1,3-dinitrobenzene. CH 3 COCl/AlCl 3. C 6 H 5 Br Bromobenzene. Conc. H 2 SO 4 /HNO 3 60 o C. Br 2 /FeBr 3. C 6 H 6. Nitrobenzene. conc. H 2 SO 4 /HNO 3.

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C 6 H 6

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  1. Benzene Reaction Chart C6H5CH2CH3 Sulphonic acid C6H5SO3H Zn/Hg c. HCl C6H5COCH3 Conc. H2SO4 1,3-dinitrobenzene CH3COCl/AlCl3 C6H5Br Bromobenzene Conc. H2SO4/HNO3 60oC Br2/FeBr3 C6H6 Nitrobenzene conc. H2SO4/HNO3 CH3Cl/AlCl3 • Sn, conc. HCl • NaOH C6H5CH3 Methylbenzene Aniline HNO2, 0oC Alkaline Naphthal-2-enol CuBr Aryl diazonium ion, C6H5-N=N+ Bromobenzene H2O Azo Dye (coupling) Phenol H3PO2 CuCN CyanoBenzene Benzene

  2. Diazonium Salt Reactions

  3. Nitration

  4. SO3H group is bulky and attack is preferred at para-position.

  5. Strongly favored unfavorable

  6. Unfavorable Strongly favored

  7. C-acylation HOC6H4COCH3 C6H5OCH3 Benzenesulphonic acid CH3COCl/AlCl3 CH3Br Conc. H2SO4 O-acylation C6H5O- Na+ C6H5OCOCH3 2-bromophenol or 4-bromophenol NaOH CH3COCl Or CH3CO2H Br2/FeBr3 C6H5OH Br2(aq) CH3Cl/AlCl3 2,4,6-tribromophenol conc. H2SO4/HNO3 4-methylphenol Or 2-methylphenol Na Ar-N=N+ 4-nitrophenol Or 2-nitrophenol Sodium phenoxide C6H5O- Na+ + H2 Coupling reaction Phenol Reaction Chart

  8. Reaction of aromatic ring of phenols Major -SO3H is sensitive to hindrance

  9. OUT SYL OUT SYL

  10. The Low Reactivity of Halobenzenes • The CX bond of halobenzenes is stronger than that of haloalkanes • partial  bond character •  Breaking of the CX bond requires a larger • amount of energy •  substitution reactions of halobenzenes are • difficult to occur • The delocalization of  electrons •  makes the polarity of the CX bond decreased •  the electropositive carbon centrebecomes much • less susceptible to nucleophilic attack • The delocalized electrons in the benzene ring •  repel any approaching nucleophiles •  Halobenzenes are unreactive towards SN2 reactions • Benzene cations are highly unstable •  loss of aromaticity •  Halobenzenes are unreactive towards SN1 reactions

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