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vozosoba's version from 2016-07-08 21:27

Ch. 11 Rxs

Question Answer
Benzene -> CyclohexaneH2, Pt
Ph-C-R -> Ph-(C-Br)RNBS, ROOR, ^, CCl4 NOTE R may be H
Ph-C=C-R -> Ph-(C-X)-C-RHX, X= Cl or Br NOTE R may be H
Ph-C=C-R -> Ph-C-(C-Br)-RHBr, ROOR NOTE R may be H
Ph-(C-R)R -> Ph-CO2HNa2Cr2O7, H2O, H2SO4, ^ OR KMnO4, H2O, ^, HCl NOTE R may be H
Ph-R -> Diene-RNa, NH3, EtOH NOTE R may be H
Ph-CH3 -> Ph-CH2ClCl2, hv or ^
Ph-CH3 -> Ph-CO2HO2, cyto P45Os
Ph -> Ph-EpoxidecytoP45Us
Ph-(C-Br)-R -> Ph-(C-CN)-RNaCN (KCN), H2O, CH3OH MECHANISM****
Ph-C-Cl -> Ph-C-N3NaN3, DMSO
Styrene -> Ph-(C-Br)-RHBr MECHANISM******
PH-5ringalkene-> Ph-5RingAlcoholH2O, H2SO4
Ph-C=C-R -> Ph-C=OH1. O3 2. (CH3)2S
Ph-C=OOH -> Ph + CaCO3CaO
Ph-C-Br -> Ph-C-OHNaOH
Br-C-C -> C=CKOCH2CH3, HOCH2CH3
Ph-C=C-R -> PH-(C-Br)-(C-Br)-RBr2
(C-Br)-(Br-C) -> C---C1. NaNH2, NH3 2. H2O
Ph-C---C -> Ph-(H-C)-(C-H)-CH3 (cis)H2, lindlar pd
Ph-C---C -> Ph-(H-C)-(C-H)-CH3 (trans)1 equivilent H2
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Ch. 12 Rxs

Question Answer
Ph -> Ph-NO2HNO3, H2SO4
Ph -> Ph-SO3HSO3, H2SO4
Ph -> Ph-xX2, FeX3
Ph -> Ph-RRX, AlCl3
Ph -> Ph-(C=O)RR(C=O)Cl, AlCl3
R(C=O)OH -> R(C=O)ClSOCl2
Ph-(C=O)R -> Ph-C-RZn(Hg), HCl or H2NNH2, KOH, ^, triethylene glycol
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Section Benzene Common Names

 

Question Answer
Benzaldehyde
Benzoic Acid
Styrene
Acetophenone
Phenol
Anisole
Aniline
Benzene
Toluene
Naphthalene
Benzophenone
Acetanilide
Biphenyl
Benzyl Alcohol
Benzyl Chloride
Benzylic Carbon
Anthracene
Phenanthrene
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Question Answer
Pyridine
Pyrrole
Furan
Thiophene
Quinoline
Isoquinoline
Indole
Benzofuran
Benzothiophene
Imidazole
Oxazole
Thiazole
Benzimidazole
Purine
Adenine
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Ch. 14 Rxs

Question Answer
R3CX -> R3CLiLi
C=C-X -> C=C-LiLi
Ph-X -> Ph-LiLi
R3CX -> R3CMgXMg
C=C-X -> C=C-MgXMg
Ph-X -> Ph-MgXMg
RMgX + R'2C=O -> -> R'2COHRH3O+
RMgX + R'C=OOCH3 -> -> R'COHR2H3O+
RLi -> R2CuLiCuX
(RCH2)2CuLi + XCH2R' -> ?? -> RCH2CH2R'
(RCH2)2CuLi + XAr -> ?? -> RCH2Ar
(RCH2)2CuLi + X-C=C -> ?? -> RCH2-C=C
Ar2CuLi + XCH2R -> ?? -> ArCH2R
(C=C)2-CuLi + XCH2R' -> ?? -> C=C-CH2R'
CH2I2 -> ICH2ZnIZn(cu)
C=C -> c-c-cICH2ZnI, Et2O Simmons-smith MECHANISM*****
Ph-C=C-C=OH -> Ph-C-C-C=OHH2, Rh[P(Ph)3]3Cl
Grubs Catalyst????
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Ch. 15 Rxs

Question Answer
RCH2OH -> RC=OHPCC/PDC, CH2Cl2
RCH2OH -. RC=OOHNa2Cr2O7, H2SO4, H2O
R(C-OH)HR' -> RC=OR'PCC/PDC, CH2Cl2, OR Na2Cr2O7, H2SO4, H2O
RCH2OH -> RCH2OCH2RH2SO4, <150C
ROH -> R'C=OORR'C=OOH, H2SO4 OR R'C=OCl OR R'C=OOC=OR'
RCHOH-HOCR'R" -> RC=OH + R'C=OR"HIO4
C=C -> COH-COHOsO4, (CH3)3COOH, HO-, (CH3)3COH
RC=OH -> RCH2OHNaBH4, CH3OH OR 1. LiAlH4 Et2O 2. H2O OR H2 WITH Ni, Pd, Pt, OR Ru
RC=OR' -> R(C-OH)HR'NaBH4, CH3OH OR 1. LiAlH4 Et2O 2. H2O OR H2 WITH Ni, Pd, Pt, OR Ru
RC=OOH -> RCH2OH1. LiAlH4 Et2O 2. H2O
RC=OOR' -> RCH2OH + R'OH1. LiAlH4 Et2O 2. H2O
O--CC -> RCH2CH2OH1. RMgX 2. H3O+
S for RCOH -> RC=OH(CH3)2S+-O- , CLC=O-C=OCl, CH2Cl2, -50C 2) (CH3CH2)3N
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Section Ch.16

Question Answer
ROH -> ROCH2R'1. Na 2. R'CH2X For satisfactory yields, the alkyl halide/sulfonate should be methyl or 1 o
RSH -> RSCH2R' 1. NaOH 2. R'CH2X
RSR' -> R(S+-CH2)R' X-RCH2X
ROR' -> RX + R'XHX (only Br or I)
Br-(R-C)-(C-R')-OH -> R-(C-o-C*)-R'NaOH
R-(H-C-o-C*-R')-R" -> R,H-(Nu-C)-(C-OH)R',R''Nu-, protic solvent (less subtituted)
C=C -> C-O-C*ICH2ZnI, Et2O
Nu- ?HONa, RONa, HSNa, RSNa, NaCN, NaN3, NH3
protic solvent H2O, CH3OH, or CH3CH2OH
R-(H-C-o-C*-R')-R" -> R,H-(OH-C)-(C-Nu)R',R''NuH, H+ (more substituted)
NuH, H+ROH, H2SO4, H2O, HClO4, HBr
(C-o-C*')-R -> R'CH2(C-OH)HR1. R'MgX 2. H3O+
(C-o-C*')-R -> CH3(C-OH)HR1. LiAlH4 2. H2O
C=C => (C-OCH3)-CH3CH3OH, H2SO4
Br -> -O-NaOCH2CH3, CH3Ch2OH
HOR -> NaORNANH2, NH3
HOR -> BrRPBr3
C=C -> (C-oC*)RC=OOH
C=C -> BrC-C-OHBr2, H2O
memorize

Section Ch.17

Question Answer
RC=OH ->R(C=O)OHNa2Cr2O7, H2SO4, H2O
RC=OH -> R(C-OH)HCNNaCN, then H2SO4
RC=OH -> R(C=NR)HRNH2
RCH2C=OH -> RCH=(C-NR2)HR2NH
RC=OH -> R-CH=(C-R')-R'(C6H5)3+-PCR'R'
RC=OR' -> R((C-OH)-CN)R'NaCN, then H2SO4
C=C -> C=OH + C=OH1.O3 2. Zn, H2O
RC=OR' -> R(C=NR)R'RNH2
RCH2(C=O)R' -> RCH=(C-NR2)R'R2NH
R(C=O)R' -> R-(C-R')=(C-R')-R"(C6H5)3+-PCR'R'
R'R"CHX -> (C6H5)3+-PCR'R'1. (C6H5)3P 2. butyllithium
R(C=O)H -> RO-(R-(C)-H)-ORROH TsOH
R(C=O)R' -> RO-(R-(C)-R')-ORROH TsOH
RO-(R-(C)-H)-OR -> R(C=O)HH2O HClO4
RO-(R-(C)-R')-OR -> R(C=O)R'H2O HClO4
RCH=CH2 + H2 + C*O -> RCH2CH2(C*=O)HCO2(CO)8
memorize

Section Ch. 18

Question Answer
C=OH -> -C=OOHNaCr2O7, H2SO4, heat
C-OH -> C=OOHchromic Acid
c---C -> C=OOH + C=OOH1.O3 2.Zn,H2O
primary, secondary benzylic carbon -> carboxylic acidNa2Cr2O7, H2SO4
6Cring-Br -> 6Cring-C=OOH1.Mg, H2o 2.CO2, Et2O 3.H3O+ OR 1. NaCN, CH3CN 2. H2O, H2SO4
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Section 19

Question Answer
R(C=O)OH -> RCO2- + HBB-
R(CO)OH -> R(CO)ClSOCl2
R(CO)OH -> R(CO)ORR'OH, H2SO4
RCH2(C=O)OH -> R(C-Br)H(C=O)OH1. Br2, P 2. H2O
RCH2(C=O)OH -> R(C-Br)H(C=O)OR1. Br2, P 2. ROH
R(C-Br)H(C=O)OH -> R(C-Nu)H(C=O)OHNu
Nu = OHK2CO3, H2O, Heat
Nu = NH2NH3, H20
R-(HO-C)-C-C-(C=O)OH -> 4C1O ring, R-C-O-C=Ospontaneous
R-(HO-C)-C-C-C-(C=O)OH -> 5C1O ring, R-C-O-C=Ospontaneous
RCN -> RC=OOHH2O, H2SO4, heat
RMgX -> RC=OOH1.CO2 2. H3O+
memorize

Section Ch20

Question Answer
RCH2(C=O)H -> R(C-X)H(C=O)HX2, H+ X = Cl or Br
RCH2(C=O)CH2R -> R(C-X)H(C=O)CH2RX2, H+ Note Unsymetrical Ketones give mixtures of regioisomers
RCH2(C=O)CH3 -> RCH2(C=O)OH + CHX31. X2, NaOH 2. H2O+ X = Cl, Br, or I
RCH2(C=O)H -> RCH2(C-OH)H(C-R)H(C=O)HNaOH, CH3CH2OH cold
RCH2(C=O)H -> RCH2CH=(C-R)(C=O)HNaOH, CH3CH2OH warm
Ar(C=O)H + RCH2(C=O)R' -> ArCH=(C-R)(C=O)R' NaOH, CH3CH2OH Note R' may be Ar
R-(R-C)=CH-(C=O)R -> Nu-(R-(R-C))-CH2-(C=O)RNu
Nu- = CN-use NACN, H+
Nu- = N3-use NaN3, H+
Nu- = RS-use RSNa, H2O
R-(R-C)=CH-(C=O)R -> R'-(R-(R-C))-CH2-(C=O)RR'2CuLi
RCH2(C=O)CHR2 -> RCD2(C=O)CDR2NaOD, D2O (all H adjacent to C=O)
memorize

Section Ch21

Question Answer
RC=OCl -> RC=OOHH2O
RC=OCl -> RC=OOC=ORRC=OOH
RC=OCl -> RC=OORROH
RC=OCl -> RC=ON- -HN- - Note HN- - may be NH3, RNH2, or R2NH
RC=OOC=OR -> RC=OOHH2O
RC=OOC=OR -> RC=OORROH
RC=OOC=OR -> RC=ON- -HN- - Note HN- - may be NH3, RNH2, or R2NH
RC=OOR -> RC=OOH1. NaOH, H2O, heat 2.H3O+
RC=OOR -> RC=ON- -HN- - Note HN- - may be NH3, RNH2, or R2NH
RC=ON- - -> RC=OOHH2O, H2SO4, heat
RCN -> RC=OOHH2O,H2SO4,heat
RCN -> RC=OR'1.R'MgX 2. H3O+, heat
memorize

Section Ch22

Question Answer
RN3 -> RNH21. LiAlH4 2. H2O
RCN -> RCH2NH21. LiAlH4 2. H2O
RC=ON(-R2) -> RCH2N(-R2)1. LiAlH4 2. H2O
R2NH -> R2NR'R'X
R3N -> R3N+R'X-R'X
R2NH -> RC=ONR2RC=OCl or RC=OOC=OR
RNH2 + RC=OR -> RC(=NR)RH+
R2NH + R2CHC=OR -> R2C=C(-NR2)RH+
RNH2 + RC=OR -> RC-(NHR)HRH2, Ni, or NaBH3CN
(CH3)3N+-C(CH3)RCHR2 -> H2C=C(-R)CHR21.Ag2O 2.heat
Ar-NO2 -> Ar-NH21.Sn, HCl 2. NaOH
Ar-NH2 -> Ar-N2+Cl-NaNO2, HCl, H2O, 0C
Ar-N2+Cl- -> Ar-ZZ
Z = F1.HBF4 2. heat
Z = ClCuCl
Z = BrCuBr
Z = IKI
Z = CNCuCN
Z = OHH2O
Z = HCH3CH2OH or H3PO2
Gabriel Amine Synthesis?1.NH3, heat 2.-OH, H20 3.R-X 4. H2SO4, H2O 5. NaOH, H2O
Acylate Amine Synthesis?1.CH3C=OCl 2. HNO3, H2SO4 3. H2O, H2SO4
NitrosationRNH2 + NaNO2,HCL -> N2+Cl- , R2NH + NaNO2,HCL -> N-N=O
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