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2016-07-08 21:27
Ch. 11 Rxs
Question | Answer |
Benzene -> Cyclohexane | H2, Pt |
Ph-C-R -> Ph-(C-Br)R | NBS, ROOR, ^, CCl4 NOTE R may be H |
Ph-C=C-R -> Ph-(C-X)-C-R | HX, X= Cl or Br NOTE R may be H |
Ph-C=C-R -> Ph-C-(C-Br)-R | HBr, ROOR NOTE R may be H |
Ph-(C-R)R -> Ph-CO2H | Na2Cr2O7, H2O, H2SO4, ^ OR KMnO4, H2O, ^, HCl NOTE R may be H |
Ph-R -> Diene-R | Na, NH3, EtOH NOTE R may be H |
Ph-CH3 -> Ph-CH2Cl | Cl2, hv or ^ |
Ph-CH3 -> Ph-CO2H | O2, cyto P45Os |
Ph -> Ph-Epoxide | cytoP45Us |
Ph-(C-Br)-R -> Ph-(C-CN)-R | NaCN (KCN), H2O, CH3OH MECHANISM**** |
Ph-C-Cl -> Ph-C-N3 | NaN3, DMSO |
Styrene -> Ph-(C-Br)-R | HBr MECHANISM****** |
PH-5ringalkene-> Ph-5RingAlcohol | H2O, H2SO4 |
Ph-C=C-R -> Ph-C=OH | 1. O3 2. (CH3)2S |
Ph-C=OOH -> Ph + CaCO3 | CaO |
Ph-C-Br -> Ph-C-OH | NaOH |
Br-C-C -> C=C | KOCH2CH3, HOCH2CH3 |
Ph-C=C-R -> PH-(C-Br)-(C-Br)-R | Br2 |
(C-Br)-(Br-C) -> C---C | 1. 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-NO2 | HNO3, H2SO4 |
Ph -> Ph-SO3H | SO3, H2SO4 |
Ph -> Ph-x | X2, FeX3 |
Ph -> Ph-R | RX, AlCl3 |
Ph -> Ph-(C=O)R | R(C=O)Cl, AlCl3 |
R(C=O)OH -> R(C=O)Cl | SOCl2 |
Ph-(C=O)R -> Ph-C-R | Zn(Hg), HCl or H2NNH2, KOH, ^, triethylene glycol |
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Section Benzene Common Names
Ch. 14 Rxs
Question | Answer |
R3CX -> R3CLi | Li |
C=C-X -> C=C-Li | Li |
Ph-X -> Ph-Li | Li |
R3CX -> R3CMgX | Mg |
C=C-X -> C=C-MgX | Mg |
Ph-X -> Ph-MgX | Mg |
RMgX + R'2C=O -> -> R'2COHR | H3O+ |
RMgX + R'C=OOCH3 -> -> R'COHR2 | H3O+ |
RLi -> R2CuLi | CuX |
(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 -> ICH2ZnI | Zn(cu) |
C=C -> c-c-c | ICH2ZnI, Et2O Simmons-smith MECHANISM***** |
Ph-C=C-C=OH -> Ph-C-C-C=OH | H2, Rh[P(Ph)3]3Cl |
Grubs Catalyst?? | ?? |
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Ch. 15 Rxs
Question | Answer |
RCH2OH -> RC=OH | PCC/PDC, CH2Cl2 |
RCH2OH -. RC=OOH | Na2Cr2O7, H2SO4, H2O |
R(C-OH)HR' -> RC=OR' | PCC/PDC, CH2Cl2, OR Na2Cr2O7, H2SO4, H2O |
RCH2OH -> RCH2OCH2R | H2SO4, <150C |
ROH -> R'C=OOR | R'C=OOH, H2SO4 OR R'C=OCl OR R'C=OOC=OR' |
RCHOH-HOCR'R" -> RC=OH + R'C=OR" | HIO4 |
C=C -> COH-COH | OsO4, (CH3)3COOH, HO-, (CH3)3COH |
RC=OH -> RCH2OH | NaBH4, 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 -> RCH2OH | 1. LiAlH4 Et2O 2. H2O |
RC=OOR' -> RCH2OH + R'OH | 1. LiAlH4 Et2O 2. H2O |
O--CC -> RCH2CH2OH | 1. 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'X | HX (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)HR | 1. R'MgX 2. H3O+ |
(C-o-C*')-R -> CH3(C-OH)HR | 1. LiAlH4 2. H2O |
C=C => (C-OCH3)-CH3 | CH3OH, H2SO4 |
Br -> -O- | NaOCH2CH3, CH3Ch2OH |
HOR -> NaOR | NANH2, NH3 |
HOR -> BrR | PBr3 |
C=C -> (C-oC*) | RC=OOH |
C=C -> BrC-C-OH | Br2, H2O |
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Section Ch.17
Question | Answer |
RC=OH ->R(C=O)OH | Na2Cr2O7, H2SO4, H2O |
RC=OH -> R(C-OH)HCN | NaCN, then H2SO4 |
RC=OH -> R(C=NR)H | RNH2 |
RCH2C=OH -> RCH=(C-NR2)H | R2NH |
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=OH | 1.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)-OR | ROH TsOH |
R(C=O)R' -> RO-(R-(C)-R')-OR | ROH TsOH |
RO-(R-(C)-H)-OR -> R(C=O)H | H2O HClO4 |
RO-(R-(C)-R')-OR -> R(C=O)R' | H2O HClO4 |
RCH=CH2 + H2 + C*O -> RCH2CH2(C*=O)H | CO2(CO)8 |
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Section Ch. 18
Question | Answer |
C=OH -> -C=OOH | NaCr2O7, H2SO4, heat |
C-OH -> C=OOH | chromic Acid |
c---C -> C=OOH + C=OOH | 1.O3 2.Zn,H2O |
primary, secondary benzylic carbon -> carboxylic acid | Na2Cr2O7, H2SO4 |
6Cring-Br -> 6Cring-C=OOH | 1.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- + HB | B- |
R(CO)OH -> R(CO)Cl | SOCl2 |
R(CO)OH -> R(CO)OR | R'OH, H2SO4 |
RCH2(C=O)OH -> R(C-Br)H(C=O)OH | 1. Br2, P 2. H2O |
RCH2(C=O)OH -> R(C-Br)H(C=O)OR | 1. Br2, P 2. ROH |
R(C-Br)H(C=O)OH -> R(C-Nu)H(C=O)OH | Nu |
Nu = OH | K2CO3, H2O, Heat |
Nu = NH2 | NH3, H20 |
R-(HO-C)-C-C-(C=O)OH -> 4C1O ring, R-C-O-C=O | spontaneous |
R-(HO-C)-C-C-C-(C=O)OH -> 5C1O ring, R-C-O-C=O | spontaneous |
RCN -> RC=OOH | H2O, H2SO4, heat |
RMgX -> RC=OOH | 1.CO2 2. H3O+ |
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Section Ch20
Question | Answer |
RCH2(C=O)H -> R(C-X)H(C=O)H | X2, H+ X = Cl or Br |
RCH2(C=O)CH2R -> R(C-X)H(C=O)CH2R | X2, H+ Note Unsymetrical Ketones give mixtures of regioisomers |
RCH2(C=O)CH3 -> RCH2(C=O)OH + CHX3 | 1. X2, NaOH 2. H2O+ X = Cl, Br, or I |
RCH2(C=O)H -> RCH2(C-OH)H(C-R)H(C=O)H | NaOH, CH3CH2OH cold |
RCH2(C=O)H -> RCH2CH=(C-R)(C=O)H | NaOH, 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)R | Nu |
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)R | R'2CuLi |
RCH2(C=O)CHR2 -> RCD2(C=O)CDR2 | NaOD, D2O (all H adjacent to C=O) |
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Section Ch21
Question | Answer |
RC=OCl -> RC=OOH | H2O |
RC=OCl -> RC=OOC=OR | RC=OOH |
RC=OCl -> RC=OOR | ROH |
RC=OCl -> RC=ON- - | HN- - Note HN- - may be NH3, RNH2, or R2NH |
RC=OOC=OR -> RC=OOH | H2O |
RC=OOC=OR -> RC=OOR | ROH |
RC=OOC=OR -> RC=ON- - | HN- - Note HN- - may be NH3, RNH2, or R2NH |
RC=OOR -> RC=OOH | 1. NaOH, H2O, heat 2.H3O+ |
RC=OOR -> RC=ON- - | HN- - Note HN- - may be NH3, RNH2, or R2NH |
RC=ON- - -> RC=OOH | H2O, H2SO4, heat |
RCN -> RC=OOH | H2O,H2SO4,heat |
RCN -> RC=OR' | 1.R'MgX 2. H3O+, heat |
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Section Ch22
Question | Answer |
RN3 -> RNH2 | 1. LiAlH4 2. H2O |
RCN -> RCH2NH2 | 1. LiAlH4 2. H2O |
RC=ON(-R2) -> RCH2N(-R2) | 1. LiAlH4 2. H2O |
R2NH -> R2NR' | R'X |
R3N -> R3N+R'X- | R'X |
R2NH -> RC=ONR2 | RC=OCl or RC=OOC=OR |
RNH2 + RC=OR -> RC(=NR)R | H+ |
R2NH + R2CHC=OR -> R2C=C(-NR2)R | H+ |
RNH2 + RC=OR -> RC-(NHR)HR | H2, Ni, or NaBH3CN |
(CH3)3N+-C(CH3)RCHR2 -> H2C=C(-R)CHR2 | 1.Ag2O 2.heat |
Ar-NO2 -> Ar-NH2 | 1.Sn, HCl 2. NaOH |
Ar-NH2 -> Ar-N2+Cl- | NaNO2, HCl, H2O, 0C |
Ar-N2+Cl- -> Ar-Z | Z |
Z = F | 1.HBF4 2. heat |
Z = Cl | CuCl |
Z = Br | CuBr |
Z = I | KI |
Z = CN | CuCN |
Z = OH | H2O |
Z = H | CH3CH2OH 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 |
Nitrosation | RNH2 + NaNO2,HCL -> N2+Cl- , R2NH + NaNO2,HCL -> N-N=O |
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