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Carey F.A. Organic Chemistry
Carey F.A.  Organic Chemistry







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: Organic Chemistry

: Carey F.A.

:

This respected text is based on the Functional Group approach. The text retains the outstanding problems, pedagogy, depth, and prose of the second edition while providing increased emphasis on molecular modeling, a core concept in organic chemistry.


: en

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ed2k: ed2k stats

: 2004

: 1191

: 20.04.2006

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$1-\beta-D$-Ribofuranosyluracil      see Uridine
$9-\beta-D$-Ribofuranosyladenine      see Adenosine
$Ad_E 3$ mechanism      378
$PGE_1, PGE_2, PGF_{1\alpha}, PGG_2$ and $PGH_2$      see Icosanoids
$PK_a$      33 (see also Acidity)
$S_N1$ mechanism      160161 180 339341 356
$S_N2$ mechanism      163165 181 330336 356
$\alph-D$-Glucopyranose      10371038 1040
$\alpha in hydration of alkynes      379381 385
$\alpha in racemization of (R)-sec-butyl phenyl ketone      769
$\alpha of purines and pyrimidines      11561158 1167 1186
$\alpha$ and $\beta$-Ionone      1107
$\alpha$-Halo aldehydes, preparation of      757
$\alpha$-Halo carboxylic acids nucleophilic substitution in      816
$\alpha$-Halo carboxylic acids preparation of      815816 823
$\alpha$-Halo carboxylic acids reaction with ammonia      816 928
$\alpha$-Halo ketones, preparation of      757 782
$\alpha$-Helix      11431145
$\alpha$-Keratin      1144
$\alpha$-Ketoglutaric acid      11231125
$\alpha$-Olefins      see Linear $\alpha$-olefins
$\alpha$-Phellandrene      1086
$\alpha$-Pinene      187 1090
$\alpha$-Pinene hydroboration-oxidation of      252
$\alpha$-Pinene hydrogenation of      235
$\alpha$-Santonin      1104
$\alpha$-Selinene      1085 1086
$\alpha$-Terpineol      1089
$\alpha,\beta$      Unsaturated aldehydes and ketones conjugate addition to
$\beta$-Alanine      1110
$\beta$-Carotene      729 1086 1101
$\beta$-Keto acids, decarboxylation      818819 824 893 895896 905
$\beta$-Keto esters acidity of      886
$\beta$-Keto esters alkylation of      894896 907
$\beta$-Keto esters Michael addition of      901902
$\beta$-Keto esters nomenclature of      887
$\beta$-Keto esters preparation of by acylation of ketones      892893 906
$\beta$-Keto esters preparation of by Claisen condensation      887890 906
$\beta$-Keto esters preparation of by Dieckmann reaction      890891 906
$\beta$-Keto esters preparation of by mixed Claisen condensation      891892 906
$\beta$-Pinene      1090
$\beta-D$-Glucopyranose      10371038 1040 1062
$\Delta H^{\circ}$ and bond dissociation energy      174
$\Delta H^{\circ}$ and heats of reaction      84
$\Delta H^{\circ}$ relation to free energy      122123
$\Delta^9$-Tetrahydrocannabinol      1001 1074
$\epsilon$-Caprolactam      861
$\gamma$-Aminobutyric acid      1110
$\nu$ (symbol for frequency)      520
(Benzene)tricarbonylchromium      609
(E)- and (Z)-Cyclodecene      213
(E)-1,2-Dichloroethene, plane of symmetry in      286
(R)-and (S)-2-Bromooctane, stereochemistry of hydrolysis of      331333 343344
(S)-Malic acid      299300
(S)-Malic acid as resolving agent      311312
(Trifluoromethyl)benzene, nitration of      488489 492494
1, 3-Cyclooctadiene, UV-VIS spectrum      565
1,1-Dimethylethyl group      74
1,2-Benzenedicarboxylic acid      792
1,2-Dibromocyclopropane, stereoisomers of      304
1,2-Dibromoethane      257
1,2-Dimethoxyethane      666
1,2-Epoxycyclohexane hydrolysis of      683 684
1,2-Epoxycyclohexane preparation of      677
1,2-Epoxycyclohexane reactions of with hydrogen bromide      683
1,2-Epoxycyclohexane with sodium azide      931
1,2-Epoxypropane chirality center in      285 297
1,2-Epoxypropane preparation of      678
1,2-Epoxypropane reaction with phenylmagnesium bromide      681
1,2-Ethanediol      see Ethylene glycol
1,3- and 1,4-Pentadiene, relative stabilities      399400
1,3-Butadiene $\pi$-molecular orbitals      413-414
1,3-Butadiene addition of halogens to      407 418
1,3-Butadiene addition of hydrogen halides to      405407 417418
1,3-Butadiene conformations      401402
1,3-Butadiene Dieis Alder reactions of      409414
1,3-Butadiene electrostatic potential map      390
1,3-Butadiene industrial preparation of      404
1,3-Butadiene polymers of      408409
1,3-Butadiene structure and bonding      400402
1,3-Diaxial repulsion      121
1,3-Dihydroxyacetone      1064
1,3-Dihydroxyacetone phosphate      1058
1,3-Diketones acidity of      764765
1,3-Diketones alkylation of      779 781 784
1,3-Diketones enolization of      761762
1,3-Diketones preparation of      892
1,3-Propadiene      see Allene
1,4-Benzenedicarboxylic acid      806
1,4-Benzenedicarboxylic acid, condensation polymers of      868
1-Aminocyclopropanecarboxylic acid in ethylene biosynthesis      189 1110
1-Bromobutane      152 242
1-Bromobutane alkylation of acetoacetate      895
1-Bromobutane alkylation of acetylene      370371
1-Bromobutane alkylation of o-nitrophenol      1017
1-Bromobutane nucleophilic substitution in      347
1-Butanol acid-catalyzed ether formation from      635 671
1-Butanol conversion to 1-bromobutane      152
1-Butanol dehydration      211
1-Butanol Fischer esterification of      847
1-Butene      188 192
1-Butene addition of hydrogen bromide to      237 242
1-Butene addition of sulfuric acid to      272
1-Butene boiling point      708
1-Butene dipole moment of      196
1-Butene electrostatic potential map      707
1-Butene heat of combustion      197
1-Butene heat of hydrogenation      231233
1-Butyne      364 371
1-Chloro-2, 4-dinitrobenzene, nucleophilic substitution in      976
1-Chloro-2-methylpropane      177 (see also Isobutyl chloride)
1-Chlorobutane      175176
1-Chloropentane, $\sideset{^1}{}H$ and $\sideset{^{13}}{}C NMR$      548 550
1-Decanol      250251 710
1-Decene hydroboration-oxidation of      250251 626
1-Decene hydroxylation of      635
1-Dodecene, epoxidation of      261
1-Fluoro-2,4-dinitrobenzene      976 11311132
1-Heptanol oxidation of      642
1-Heptanol reaction with hydrogen bromide      152
1-Hexene addition of bromine      273
1-Hexene cis-3-Hexene, reaction of, with hydrogen bromide      236
1-Hexene heat of hydrogenation      233
1-Hexene infrared spectrum      561562
1-Hexynylmagnesium bromide      598
1-Methylcyclopentene addition of hydrogen chloride      237
1-Methylcyclopentene hydroboration-oxidation      252254
1-Methylethyl group      74 (see also Isopropyl group)
1-Methylpropyl group      74 (see also sec-Butyl group)
1-Naphthol, azo coupling of      950
1-Pentanol esterification      656
1-Pentanol reaction with thionyl chloride      180
1-Phenylethylamine, resolution      311312
18-Electron rule      608
2,2,2-Trifluoroethanol acidity of      4041
2,2,4-Trimethylpentane      266
2,2,4-Trimethylpentane, chlorination of      186
2,2-Dimethylpropane      82
2,2-Dimethylpropane chemical shifts ($\sideset{^1}{}H$ and $\sideset{^{13}}{}C$ )      549
2,2-Dimethylpropyl group      75
2,3-Butanediol, stereoisomers      303304
2,3-Dihydroxybutanoic acid, stereoisomers of      300302
2,3-Dimethyl-2-butene      207 208209
2,3-Dimethyl-2-butene heat of hydrogenation      233
2,3-Dimethyl-l-butene      207 208209
2,3-Pentadiene, enantiomers      403
2,4,5-T      see 2 acid
2,4,5-Trichlorophenol      10091010
2,4,5-Trichlorophenoxyacetic acid      10091010
2,4-Dinitrophe nylhydr azine      727
2,4-Pentanedione $pK_a$ of      36 764765
2,4-Pentanedione $\alpha$-alkylation of      781
2,4-Pentanedione enol content of      761762
2-Bromo-2-methylbutane elimination reactions      212 218
2-Bromo-2-methylbutane substitution versus elimination in      349350
2-Bromo-3-methylbutane, rearrangement in hydrolysis of      344345
2-Bromobutane      146 237
2-Bromobutane alkylation of diethyl malonate      898899
2-Bromobutane preparation of      152 354
2-Butanol      see also sec-Butyl alcohol
2-Butanol chirality center in      284 290
2-Butanol enantiomers      289291
2-Butanol reaction with hydrogen bromide      153 354
2-Butanone enolization of      761
2-Butanone heat of combustion      708
2-Butanone proton magnetic resonance spectrum      739
2-Butyne      364 371
2-Chloro-1,3,5-trinitrobenzene      976
2-Chloro-2-methylpropane      177 (see also tert-Butyl chloride)
2-Chlorobutane      175176
2-Deoxy-D-ribose      1042 1064 11591160 1187
2-Heptanone      388 895
2-Methyl-2-butanol dehydration of      204
2-Methyl-2-butanol preparation of      247
2-Methyl-2-butene acid catalyzed hydration      247 626
2-Methyl-2-butene hydroboration-oxidation      251
2-Methyl-2-butene hydrogenation of      231
2-Methyl-2-butene preparation of      204 212 218
2-Methyl-2-butene reaction of with hydrogen bromide      245
2-Methyl-2-butene reaction of with hydrogen chloride      237238
2-Methyl-2-propanol      152 (see also tert-Butyl alcohol)
2-Methyl-2-propanol acid-catalyzed dehydration      203
2-Methylbutane      82 (see also Isopentane)
2-Methylcyclohexanol, dehydration of      204
2-Methylpentane      72
2-Methylpentane $pK_a$ of      36
2-Methylpentane $\sideset{^1}{}H NMR$      739
2-Methylpentane bromation of      177
2-Methylpentane reaction with tert-butylamine      744
2-Methylpropanal acidity of      764
2-Methylpropane      73 (see also Isobutane)
2-Methylpropane acidity of      593
2-Methylpropane bond dissociation energies in      170171 439
2-Methylpropane chemical shifts carbon      549
2-Methylpropane chemical shifts proton      527 549
2-Methylpropane chlorination      177
2-Methylpropene      see also Isobutene; Isobutylene
2-Methylpropene addition of hydrogen bromide to      237
2-Methylpropene addition of methanol to      672
2-Methylpropene bromohydrin formation      259
2-Methylpropene dimerization      266
2-Methylpropene dipole moment      196
2-Methylpropene heat of combustion      197
2-Methylpropene hydration mechanism      248
2-Methylpropene preparation of      203
2-Methylpropyl group      74 (see also Isobutyl group)
2-Naphthol, nitrosation of      1003
2-Octanol      355 596
2-Phenyl-2-butanol      600 640
2-Phenylethanol      639
2-Phenylethanol $\sideset{^1}{}H NMR$ spectrum      653
2-Phenylpropene hydroxylation of      654
2-Propanol      145 (see also Isopropyl alcohol)
3,3-Dimethyl-1-butene      209
3,3-Dimethyl-2-butanol dehydration and rearrangement of      208210
3-Aminopropanoic acid      see $\beta$-Alanine
3-Heptanone      740
3-Methyl-2-butanol preparation of      251
3-Methyl-2-butanol reaction with hydrogen chloride      355
3-Methyl-2-butenyl pyrophosphate      see Dimethylallyl pyrophosphate; Isopentenyl pyrophosphate
3-Methylpentane      73
3-Pentanol, dehydration      206
3-Pentanone cyanohydrin      743
3-Pentanone mass spectrum      741
4-Aminobutanoic acid      see $\gamma$-Aminobutyric acid
4-tert-Butylcyclohexyl bromide, rate of elimination of cis and trans isomers      216217
6-Mercaptopurine      1158
Abscicic acid      1086
Absolute configuration      289293 316
Absorption of electromagnetic radiation      521
Absorption of electromagnetic radiation in infrared spectroscopy      559
Absorption of electromagnetic radiation in nuclear magnetic resonance spectroscopy      522524
Absorption of electromagnetic radiation in ultraviolet-visible spectroscopy      565566
Absorptivity      see Molar absorptivity
Acetaldehyde      704
Acetaldehyde bond angles      706
Acetaldehyde enolization of      760
Acetaldehyde formation of in biological oxidation of ethanol      645647
Acetaldehyde in Strecker synthesis of D,L-alanine      1121
Acetaldehyde preparation of by hydration of acetylene      381
Acetaldehyde preparation of from ethylene      269 644
Acetaldehyde reactions of aldol addition      769
Acetaldehyde reactions of hydration      714
Acetaldehyde reactions of with hexylmagnesium bromide      596
Acetaldol      769
Acetals      720724 744
Acetals as protecting group      723724
Acetals glycosides as      1044
Acetals hydrolysis of      722723 724
Acetals preparation of      720723 744
Acetamide      833
Acetanilide      933
Acetanilide preparation and nitration of      941942
Acetanilide reduction of      933
Acetanilide resonance in      940
Acetic acid $pK_{\alpha}$ of      36 43
Acetic acid acidity of      43 795797 801 803
Acetic acid conversion to mevalonic acid      1087 1091
Acetic acid electrostatic potential maps acetate ion      796 797
Acetic acid electrostatic potential maps acid      794 797
Acetic acid esterification of      638 656
Acetic acid industrial preparation and use of      806 841
Acetic acid natural occurrence of      4 791 806
Acetic acid natural products derived from      10691108
Acetic anhydride      831 833
Acetic anhydride in Friedel Crafts acylation      486 502 504 510 842
Acetic anhydride preparation of      841
Acetic anhydride reactions of with $\alpha$-D-glucopyranose      1058
Acetic anhydride reactions of with alcohols      656 843 847
Acetic anhydride reactions of with arylamines      843 940
Acetic anhydride reactions of with glycine      1123
Acetic anhydride reactions of with phenols      10041006 1017
Acetic anhydride reactions of with salicylic acid      1006
Acetic anhydride reactions of with sucrose      1064
Acetic anhydride UV absorption      873
Acetoacetic ester synthesis      894896 907
Acetoacetyl acyl carrier protein      1076
Acetoacetyl coenzyme A      1076 1091
Acetone as solvent      329
Acetone bond angles      706
Acetone enolization of      758 760
Acetone enolization of electrostatic potential map      755
Acetone reactions of aldol condensation      773
Acetone reactions of bromination      758759
Acetone reactions of cyanohydrin formation      719
Acetone reactions of hydration      714
Acetone reactions of reductive amination of      957
Acetone reactions of Wittig reaction      744
Acetophenone      432 486 706
Acetophenone $pK_a$ of      37
Acetophenone acidity of      764
Acetophenone acylation of enolate      892
Acetophenone phenylhydrazone      727
Acetophenone reactions of aldol condensation      775
Acetophenone reactions of bromination      504
Acetophenone reactions of chlorination      505
Acetophenone reactions of nitration      505
Acetophenone reactions of with butyllithium      627
Acetophenone reactions of with ethylmagnesium bromide      600
Acetyl chloride      831 833
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