Microscale Organic Laboratory with Multistep and Multiscale Syntheses

646 Pages·2017·16.57 MB·english

by  Dana W. Mayo

I 10% Pd/C
+ OH
B(OH)2 OH aq. K2CO3
O CH SIXTH EDITION
3
HO O Microscale
H3C O
HOH3C
HO
O
H C
3
Organic
Laboratory
With Multistep and
Multiscale Syntheses
Dana Mayo
O2N O2N
H H Ronald Pike
hv
N N
N H N
David Forbes

o
18VIIIA 2 HeHelium4.0026 10 NeNeon20.180 18 ArArgon39.948 36 KrKrypton83.798 54 XeXenon131.29 86 RnRadon(222) 118 Uu (294)
17VIIA 9 FFluorine18.998 17 ClChlorine35.453 35 BrBromine79.904 53 IIodine126.90 85 AtAstatine(210) 117 Uus (294) 71 LuLutetium174.97 103 Lrawrencium(262)
L
m
16VIA 8 OOxygen15.999 16 SSulfur32.065 34 SeSelenium78.96 52 TeTellurium127.60 84 PoPolonium(209) 116 LvLivermoriu(293) 70 YbYtterbium173.04 102 NoNobelium(259)
15VA 7 NNitrogen14.007 15 Phosphorus30.974 33 AsArsenic74.922 51 SbAntimony121.76 83 BiBismuth208.98 115 Uup (288) 69 TmThulium168.93 101 Mdendelevium(258)
P M
14IVA 6 CCarbon12.011 14 SiSilicon28.086 32 GeGermanium72.64 50 SnTin118.71 82 PbLead207.2 114 FlFlerovium(289) 68 ErErbium167.26 100 FmFermium(257)
TS 13IIIA 5 BBoron10.811 13 AlAluminum26.982 31 GaGallium69.723 49 InIndium114.82 81 TlThallium204.38 113 Uut (284) 67 HoHolmium164.93 99 EsEinsteinium(252)
EOFTHELEMEN :IUPAC recommendations:cts Service group notation 101112VIIIBIBIIB 282930 NiCuZnNickelCopperZinc58.69363.54665.409 464748 PdAgCdSilverPalladiumCadmium106.42107.87112.41 787980 PtAuHgPlatinumGoldMercury195.08196.97200.59 110111112 DsRgCnDarmstadtiumRoentgeniumCopernicium(281)(272)(285) 656466 GdTbDyDysprosiumGadoliniumTerbium158.93162.50157.25 969798 CmBkCfBerkeliumCuriumCalifornium(247)(247)(251)
BLE al Abstra 9VIIIB 27 CoCobalt58.933 45 RhRhodium102.91 77 IrIridium192.22 109 MtMeitnerium(268) 63 EuEuropium151.96 95 AmAmericium(243)
A c
TC Chemi 8VIIIB 26 FeIron55.845 44 RuRuthenium101.07 76 OsOsmium190.23 108 HsHassium(277) 62 SmSamarium150.36 94 PuPlutonium(244)
PERIODI :6Atomic number C:Symbol :Name (IUPAC) Carbon:Atomic mass 12.011 4567IVBVBVIBVIIB 22232425 CrMnVTiTitaniumVanadiumChromiumManganese47.86750.94251.99654.938 40434142 NbMoTcZrZirconiumNiobiumTechnetiumMolybdenum91.22492.90695.94(98) 72757374 HfWTaReTungstenRheniumHafniumTantalum178.49180.95183.84186.21 104105106107 RfDbSgBhDubniumSeaborgiumBohriumRutherfordium(262)(266)(264)(261) 58596061 CePmNdPrCeriumNeodymiumPromethiumPraseodymium140.12140.91(145)144.24 90919293 ThUNpPaThoriumProtactiniumNeptuniumUranium232.04231.04(237)238.03
3IIIB 21 ScScandium44.956 39 YYttrium88.906 57 *LaLanthanum138.91 89 #AcActinium(227) e Series e Series
2IIA 4 BeBerylium9.0122 12 MgMagnesium24.305 20 CaCalcium40.078 38 SrStrontium87.62 56 BaBarium137.33 88 RaRadium(226) Lanthanid # Actinid
*
1IA 1 HHydrogen1.0079 3 LILithium6.941 11 NaSodium22,990 19 KPotassium39.098 37 RbRubidium85.468 55 CsCesium132.91 87 FrFrancium(223)
Common Organic Solvents: Table of Properties
boiling melting solubility flash
point point density in water Dielectric point
Solvent formula MW ((cid:2)C) ((cid:2)C) (g/mL) (g/100g) Constant ((cid:2)C)
acetic acid C H O 60.05 118 16.6 1.049 Miscible 6.15 39
2 4 2
acetone C H O 58.08 56.2 (cid:2)94.3 0.786 Miscible 20.7(25) (cid:2)18
3 6
acetonitrile C H N 41.05 81.6 (cid:2)46 0.786 Miscible 37.5 6
2 3
benzene C H 78.11 80.1 5.5 0.879 0.18 2.28 (cid:2)11
6 6
1-butanol C H O 74.12 117.6 (cid:2)89.5 0.81 6.3 17.8 35
4 10
2-butanol C H O 74.12 98 (cid:2)115 0.808 15 15.8(25) 26
4 10
2-butanone C H O 72.11 79.6 (cid:2)86.3 0.805 25.6 18.5 (cid:2)7
4 8
t-butyl alcohol C H O 74.12 82.2 25.5 0.786 Miscible 12.5 11
4 10
carbon tetrachloride CCl 153.82 76.7 (cid:2)22.4 1.594 0.08 2.24 —
4
chlorobenzene C H Cl 112.56 131.7 (cid:2)45.6 1.1066 0.05 5.69 29
6 5
chloroform CHCl 119.38 61.7 (cid:2)63.7 1.498 0.795 4.81 —
3
cyclohexane C H 84.16 80.7 6.6 0.779 (cid:3)0.1 2.02 (cid:2)20
6 12
1,2-dichloroethane C H Cl 98.96 83.5 (cid:2)35.3 1.245 0.861 10.42 13
2 4 2
diethyl ether C H O 74.12 34.6 (cid:2)116.3 0.713 7.5 4.34 (cid:2)45
4 10
diethylene glycol C H O 106.12 245 (cid:2)10 1.118 10 31.7 143
4 10 3
diglyme (diethylene glycol
dimethyl ether) C H O 134.17 162 (cid:2)68 0.943 Miscible 7.23 67
6 14 3
1,2-dimethoxy-
ethane (glyme,DME) C H O 90.12 85 (cid:2)58 0.868 Miscible 7.2 (cid:2)6
4 10 2
dimethylether C H O 46.07 (cid:2)22 (cid:2)138.5 NA NA NA (cid:2)41
2 6
dimethyl-
formamide (DMF) C H NO 73.09 153 (cid:2)61 0.944 Miscible 36.7 58
3 7
dimethyl sulfoxide (DMSO) C H OS 78.13 189 18.4 1.092 25.3 47 95
2 6
dioxane C H O 88.11 101.1 11.8 1.033 Miscible 2.21(25) 12
4 8 2
ethanol C H O 46.07 78.5 (cid:2)114.1 0.789 Miscible 24.6 13
2 6
ethyl acetate C H O 88.11 77 (cid:2)83.6 0.895 8.7 6(25) (cid:2)4
4 8 2
ethylene glycol C H O 62.07 195 (cid:2)13 1.115 Miscible 37.7 111
2 6 2
glycerin C H O 92.09 290 17.8 1.261 Miscible 42.5 160
3 8 3
heptane C H 100.20 98 (cid:2)90.6 0.684 0.01 1.92 (cid:2)4
7 16
Hexamethylphosphoramide
(HMPA) C H N OP 179.20 232.5 7.2 1.03 Miscible 31.3 105
6 18 3
Hexamethylphosphorous
triamide (HMPT) C H N P 163.20 150 (cid:2)44 0.898 Miscible ?? 26
6 18 3
hexane C H 86.18 69 (cid:2)95 0.659 0.014 1.89 (cid:2)22
6 14
methanol CH O 32.04 64.6 (cid:2)98 0.791 Miscible 32.6(25) 12
4
methyl t-butyl
ether (MTBE) C H O 88.15 55.2 (cid:2)109 0.741 5.1 ?? (cid:2)28
5 12
methylene chloride CH Cl 84.93 39.8 (cid:2)96.7 1.326 1.32 9.08 1.6
2 2
N-methyl-2-pyrrolidinone
(NMP) CH H NO 99.13 202 (cid:2)24 1.033 10 32 91
5 9
nitromethane CH NO 61.04 101.2 (cid:2)29 1.382 9.50 35.9 35
3 2
pentane C H 72.15 36.1 (cid:2)129.7 0.626 0.04 1.84 (cid:2)49
5 12
Petroleum ether (ligroine) — — 30–60 (cid:2)40 0.656 — — (cid:2)30
1-propanol C H O 88.15 97 (cid:2)126 0.803 Miscible 20.1(25) 15
3 8
2-propanol C H O 88.15 82.4 (cid:2)88.5 0.785 Miscible 18.3(25) 12
3 8
pyridine C H N 79.10 115.2 (cid:2)41.6 0.982 Miscible 12.3(25) 17
5 5
tetrahydrofuran (THF) C H O 72.11 66 (cid:2)108.4 0.886 30 7.6 (cid:2)21
4 8
toluene C H 92.14 110.6 (cid:2)93 0.867 0.05 2.38(25) 4
7 8
triethyl amine C H N 101.19 88.9 (cid:2)114.7 0.728 0.02 2.4 (cid:2)11
6 15
water H O 18.02 100.00 0.00 0.998 — 78.54 —
2
water,heavy D O 20.03 101.3 4 1.107 Miscible ?? —
2
o-xylene C H 106.17 144 (cid:2)25.2 0.897 Insoluble 2.57 32
8 10
m-xylene C H 106.17 139.1 (cid:2)47.8 0.868 Insoluble 2.37 27
8 10
p-xylene C H 106.17 138.4 13.3 0.861 Insoluble 2.27 27
8 10
T (cid:4)20 (cid:5)C unless specified otherwise.
Source: http://virtual.yosemite.cc.ca.us/smurov/orgsoltab.htm
M I C R O S C A L E
O R G A N I C
L A B O R AT O R Y
with Multistep and
Multiscale Syntheses
SIXTH EDITION

M I C R O S C A L E
O R G A N I C
L A B O R AT O R Y
with Multistep and
Multiscale Syntheses
SIXTH EDITION
Dana W. Mayo
Charles Weston Pickard
Professor of Chemistry,Emeritus
Bowdoin College
Ronald M. Pike
Professor of Chemistry,Emeritus
Merrimack College
David C. Forbes
Professor of Chemistry
University of South Alabama
**With contributions by:
Dr.Nicholas E.Leadbeater Dr.Cynthia B.McGowan
Department of Chemistry Department of Chemistry
University of Connecticut Merrimack College
Dr.Andrew Dicks Dr.Elizabeth Stemmler
Department of Chemistry Department of Chemistry
University of Toronto Bowdoin College
VP & PUBLISHER Petra Recter
SENIOR PROJECT EDITOR Jennifer Yee
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COVER ILLUSTRATION CREDITS Dana W.Mayo
Ronald M.Pike
David C.Forbes
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Library of Congress Cataloging-in-Publication Data
Mayo,Dana W.
Microscale organic laboratory: with multistep and multiscale
syntheses/Dana W.Mayo.Charles Weston Pickard Professor of Chemistry,Emeritus,Bowdoin
College,Ronald M.Pike,Professor of Chemistry,Emeritus,Merrimack College,David C.Forbes,
Professor of Chemistry,University of South Alabama. — Sixth edition.
pages cm.
Includes bibliographical references.
ISBN 978-1-118-08340-6 (pbk.)
1. Chemistry,Organic—Laboratory manuals. I.Pike,Ronald M. II.Forbes,David C. III.Title.
QD261.M38 2013
547.0078—dc23
2013018017
Printed in the United States of America
10 9 8 7 6 5 4 3 2 1
TO JEANNE D’ARC, MARILYN, AND CAROL