Organic Chemistry, Sixth Edition

1330 Pages·2005·161.2 MB·English

by  Leroy G. Wade

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ISBN 0-13-187151-X( ReviCeowp y)
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Prefaxcxei ii
1 IntroducatinodRn e view
2 StructuarnedP ropertoifeO sr ganic Molecules 39
3 StructuarnedS tereochemiosfAt lrkya nes 81
4 The StuodfyC hemicRaela ctio1n2s5
5 Stereochemi1s6t7r y
6 Alkyl HalNiudcelse:o phSiulbisct ituatnidoE nl iminat2i1o2n
7 StructuarnedS yntheosfiA sl kenes 279
8 ReactioonfAs l kenes 321
9 Alkyne3s8 2
10 StructuarnedS yntheosfiA sl coho4l1s7
11 ReactioonfAs l coho4l6s0
12 InfrarSepde ctroscaonpdyM assS pectrome5t0r8y
13 NucleaMra gnetiRce sonanScpee ctrosc5o5p9y
14 EtherEsp,o xideasn,dS ulfid6e2s3
15 ConjugatSeyds temOsr,b itSaylm metrya,n dU ltraviolet
Spectrosc6o6p3y
16 AromatiCco mpounds 705
17 ReactioonfAs r omatiCco mpound7s4 9
18 Ketoneasn dA ldehyde8s0 5
19 Amines8 36
20 CarboxyAlciicd 8s7 0
21 CarboxyAlciicdD erivati9v7e8s
22 CondensatiaonndsA lphaS ubstitutoifoC nasr bonyl
Compound1s0 41
23 CarbohydraatnedsN ucleAicci d1s0 97
24 AminoA cidsP,e ptidaensd,P rotei1n1s5 3
25 Lipid1s2 00
26 SynthetPiocl ymers 1222
Appendic1e2s4 3
Answertso S electPerdo blemAs 1
Photo CrePdCi1t s
Index1 1
vi
Contents
Prefaxcxei ii
Aboutth eA uthoxrl i
1
Introducatnido n Revi1e w
1-1 TheO rigionfsO rganCihce mist1r y
1-2 PrincipolfAe tso miSct ruct3ur e
1-3 BondF ormation:O ctTehRteu le6
1-4 LewiSst ructu7r es
1-5 MultipBloen din8g
SummaryC:o mmonB ondinPga tte(rUnnsc harg9e d)
1-6 ElectronegaatnidBv ointdPy o lari9t y
1-7 FormaClh arge1s1
1-8 IoniSct ructu1r2e s
Summar:yC ommonB ondinPga tteirnnO sr ganCiocm poundasn dI ons1 3
1-9 Resonan1ce3
1-10S tructural F1or7m ulas
1-11M oleculFaorr mulaansd E mpiriFcoarlm ul2as0
1-12A rrhenAicuisd asn dB ases2 1
1-13B r¢nsted-LAocwirdyas n dB ase2s 2
1-14L ewiAsc idasn dB ase2s 9
Chapt1eGr l ossa3r2y
StudPyr oblem3s4
2
StructaunrdeP roperties
ofO rganiMco lecul3e9s
2-1 WaveP ropertoifEe lse ctrionnO sr bita3l9s
2-2 MoleculOarrb ita4l1s
2-3 PiB ondin4g4
2-4 HybridizaatnidMo onl eculSahra pe4s5
2-5 DrawinTgh ree-DimensMioolneaclu l4e9s
2-6 General RoufHl yebsr idizaatnidGo eno metr5y0
2-7 BondR otati5o4n
2-8 Isomeri5s6m
2-9 PolaroiftB yo ndasn dM olecul5e8s
2-10I ntermoleFcourlcaer6s 1
2-11P olarEiffteyc tosn S olubili6t5i es
2-12H ydrocarb6o8ns
2-13O rganCiocm poundCso ntainOixnygg en7 1
2-14O rganic Compounds Contain7i3n g Nitrogen
Chapt2eGr l ossa7r5y
StudPyr oble7ms7
vii
viii Contents
3
StructaunrdeS tereochemistry
ofA lkane8s1
3-1 ClassificaotfHi yodnr ocarb(oRnesv ie8w)1
3-2 MoleculFaorr muloafsA lkane8s2
3-3 NomenclatoufAr lek ane8s3
SummaryR:u lefso Nra minAgl kane8s8
3-4 PhysicParlo pertofiA elsk ane8s9
3-5 Usesa ndS ourcoefsA lkane9s1
3-6R eactioofnA sl kane9s3
3-7 StructaunrdCe o nformatoifoA nlsk ane9s4
3-8 ConformatoifoB nust an9e8
3-9 ConformatoifoH nisg heArl kane1s0 0
3-10C ycloalka1n0e0s
3-11c is-trans IsionCm yecrliosaml ka1n0e3s
3-12S tabiloiftC iyecsl oalkaRniensgS; t ra1in0 3
3-13C yclohexCaonnef ormati1o0n7s
Problem-SolSvtirnagt eDgyr:a winCgh air
Conformati1o1n0s
3-14C onformatoifoM nosn osubstiCtyuctleodh exa1n1es1
3-15C onformatoifoD niss ubstiCtyuctleodh exa1n1e4s
Problem-SolSvtirnagt egRye:c ognizciinsg
andt ranIss ome1r1s6
3-16B icyclic Mol1e1c7ul es
Chapt3eG rl ossa1r1y 9
StudPyr oblem1s2 2
4
TheS tudoyf C hemicRaela ctio1n25s
4-1 Introduc1t2io5n
4-2 ChlorinaotfMi eotnh an1e2 5
4-3 TheF ree-RadCihcaailRn e acti1o2n 6
KeyM echanisFmr:e e-dRiacaHla logenat1i2o8n
4-4 EquilibrCiounms taanntdsF reEen erg1y3 0
4-5 EnthalapnydE ntrop1y3 3
4-6 Bond-DissocEinatthiaolnp 1i3es4
4-7 Enthalpy ChianCn hgleosr ina1ti3o5n
4-8 Kinetaincdst heR atEeq uati1o3n 7
4-9 Activation aEnndte hreTge ym peratuDrepee ndence
ofR ate1s 39
4-10T ransitSitoant 1es4 0
4-11R ateosfM ultisRteeapc tio1n4s2
4-12T emperatDuerpee ndenocfHe a logenat1i4o3n
4-13S electiivnHi atlyo genat1i4o4n
4-14T heH ammondP ostul1at4e9
Problem-SolSvtirnagt ePgyr:o posiRnega ction
Mechanis1m5s1
4-15R adical Inh1i5bi3t ors
4-16R eactiIvnet ermedi1a5t5es
SummaryR:e actiIvnet ermedi1a6t0es
Chapt4eG rl ossa1r6y 0
StudPyr oble1ms6 3