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% ! $ % " & # " ' ChemGlobe Periodic Table – http://www.vcs.ethz.ch/chemglobe/ptoe/ ( ) ) " - ) *+, ( " * ., ( ) ) " - ) ( ) - *$ , - ) *+, ( ) ) ) " - *+, ( ) - *$., - ) ( ) ( ) ) " - * , * , % ! $ % " & # " ' " ! " # " C H3C 34 CH3 H H H3C + H C H3C H ) 6 7 # Br 4 C C Br H H 5 0 , 8* 5 -" ) Benzene - aromatic compound / 2 0 *1π - ) "- " , " # " R : OH Alcohols $ 9 R1 O 3 3 3 3 R2 Ethers " ) " " " / " # " > R NH2 Amines 3 3 " H H N R O OH O R1 C N H Amides $ 3 3 3 R2 Amino Acids " " ;" " $ 3 3 3 < =6 4 # " # " ?: O 1 O C R1 R C The Carbonyl Group R2 Ketone H R1 Aldehyde R C O C C OH Carboxylic acid O 1 O R1 O C O O O Anhydride δ+ Nu Cl Acid chloride δ- R2 R1 C OR Ester O R1 C N H Amide R2 % ! $ % " & # " ' % & -" – – 7 " 8 : & " ) 3 - !"$ @ " " 3 6 - "* , 9 & 0:/ "* , 4 6 ) %6 4 >" A )& ' : 3 0 & / H H ) A H O + O H OH O H N H H + H + H2O + Cl O H H H H Cl H H H N H H : !"- " " H H Cl 3 4 ) H H + OH H $ & / OH H "* , H H H H - "* , Cl H H + H H H " HO H H H H H ) H H H H Cl : 9 & B :/ & ) *& B :/ ) O H C CH3 H3C H O R C + H NaBH4 6 B Cr2O72 / H H3C Et2 O EtOH O C H R H ): O C B ) , CH3 H 3O + O H C H R H : %6 4 $ %&! ) 7 " '! OH $+!& & " 8 ) ** δ*, ROH H2O 7 '! δ+ O δ- RNH2 ** δ(, δ - Br δ(, H H Al H H 8 ) *( C *( δ+ Br H O N O δ*, " 3, &' ( 37 ( & 6 , 3 6 & 0 -% 8 " &% ! . ) 4 7- 60- 0- 6 " 8 & " 3 6 7 ( 3 ) 6 ( 3( 3 " 3 " 5 66 6 5 8 6 6 5 6 7 8 " 3 6 Two pairs of electrons on oxygen O C Pair of electrons 'in flight' %! . .' Two pairs of electrons are the double bond between carbon and oxygen H H B H H .' ' !& / 0 % ) 7 4 6 / 0 O H C H Ph Ph O Ph C ;" ) 8 7- 60- 0- 6 Ph " (! H C O H 6 A R R C R' O R' 4/ H C R' H - R R H Al H (! 4 O H H C OH R' " 8 !" C" " 6- - - 6 E / " " " " " - ) 6 $ & 9 F D - - 6 ) " 6 / ) !" C" " 6- - 3 G $ ) 4) 6 - 46 " 9 >/H " 3B )H "& 4 I "