chem 348 reagents

question

CH2I2, Zn (Cu)
Et2O2
answer

Simmons Smith (alkene->Carbene)
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O3 CH2Cl2 -78
answer

Ozonolysis (alkene-> aldehyde)
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KMnO4
answer

Oxidative Cleavage (Alkene-> carboxylic acids)
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?
answer

Cyclopropanation
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OsO4 NaIO4
THF or tBuOH
when using KMnO4:
answer

Periodate cleavage (alkene to ald/ketone)
KMno4= carboxyic acids
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HgSO4
H2SO4
answer

Hydration of Alkynes (alkyne to carboxylic acid or ketone)
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NBS hv
CCl4
answer

Allylic or Benzylic Bromination
(addition of bromine to allylic or benzylic carbon)
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1.) 9 BBN
2.) H2o2, NaOH
answer

Hydration of Alkynes
(alkyne to Aldehyde)
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1.) Hg(OAc)2, H20
2.) NaBH4
answer

oxymercuration reduction
(alkene to OH on markovnikov carbon)
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1.) BH3 THF
2.) NAOH H2O2
answer

Hydroboration oxidation
(alkene to OH on antimarkovnikov carbon)
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-:CH2
answer

Carbene formation
(alkene to carbene)
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H2N NH2
KOH
answer

Wolff Kishner RXN
Ketone taken off
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1. CH3-NH2, H+, -H2O
2. NaBH4/MeOH
answer

Reductive amination
(Ketone->Imine-> Amine)
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Starting w/ Benzene:
1.) HNO3
2.) SNCl2/HCL MeOH
3.) NaNO2/H2SO4
answer

formation of diazonium ion
N triple bond N good LG
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Diazonium +
CuCl
answer

chlorbenzene
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Diazonium +
CuBr
answer

bromobenzene
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Diazonium +
NaI
answer

Iodine-benzene
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Diazonium +
H3PO2
answer

Benzene
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Diazonium +
phenol and NaOH
answer

azo dye
question

Diazonium +
Ch3OH
answer

Reflux
benzene-OCH3
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Diazonium +
H20, 100 C OR Cu2O, Cu(NO3)2
answer

phenol
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Diazonium +
CuCn
answer

benzene w/ nitrile
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t-butyl benzene + H2CrO4, H2SO4/H2O, heat
answer

side chain oxidation
(benzene disapears, carboxylic acid w/t-butyl on it)
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Na2CrO7, H2O2, Aceton
answer

Jones Oxidation
secondary alcohol to Ketone
question

1.DMSO, (COCl)2 CH2Cl2 -60
2.Et3N -20
answer

Swern Oxidation
primary alcohol to aldehyde
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periodinane
-HOAc
answer

Primary alchol to aldehyde
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LDA, THF, -78C
answer

product of kinetic enolate
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Ph3P=CHCH2Ch3 +aldehyde or ketone
answer

wittig (carbonyl to alkene)
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1.) NaH, THF
b.) PhCHO
answer

Emmons-horner reaction
(carbonyl to alkene)
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NaCN, H+ aldeh/ketone
answer

formation of cyanohydrin
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TMSCN
answer

cyanohydrin protecting group
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ketone + HONH3CL, py or NaOAC
answer

oxime formation
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oxime+ PCl5 or H2SO4
answer

Beckmann Rearrangement
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CN DIBAL (1eq)
answer

Reduction to CHO
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CN DIBAL (2eq)
answer

Reduction to NH2
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CO2H DIBAL (2eq)
answer

Reduction to CHO
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Ester DIBAL (1eq)
answer

Reduction to CHO
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Br2, HOAc + carbonyl
answer

alpha halogenation
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ketone + mcpba
answer

ester

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