CH 320M - Synthetic Transformations

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25 Terms

1
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<p>H2 / Pt or Pd</p>

H2 / Pt or Pd

complete reduction of alkyne

<p>complete reduction of alkyne</p>
2
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<p>H2 / Ni2B</p>

H2 / Ni2B

partial reduction of alkyne to syn alkene

<p>partial reduction of alkyne to syn alkene</p>
3
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<p>H2 / Lindlar’s catalyst</p>

H2 / Lindlar’s catalyst

partial reduction of alkyne to syn alkene

<p>partial reduction of alkyne to syn alkene</p>
4
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<p>Na0 / NH3</p>

Na0 / NH3

partial reduction of alkyne to anti alkene

<p>partial reduction of alkyne to anti alkene</p>
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<p>NaNH2</p>

NaNH2

deprotonation of alkyne

<p>deprotonation of alkyne</p>
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<p>H2SO4, H2O </p>

H2SO4, H2O

nitrile hydrolysis

<p>nitrile hydrolysis </p>
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<p>HgSO4, H2SO4, H2O</p>

HgSO4, H2SO4, H2O

Markov. addition of H2O to alkyne

<p>Markov. addition of H2O to alkyne</p>
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<p>BH3, THF / H2O2, NaOH, H2O</p>

BH3, THF / H2O2, NaOH, H2O

Anti-Markov. addition of H2O to alkene

<p>Anti-Markov. addition of H2O to alkene</p>
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<p>Hg(OAc)2, H2O, THF / NaBH4</p>

Hg(OAc)2, H2O, THF / NaBH4

Markov. addition of H2O

<p>Markov. addition of H2O</p>
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<p>BH3, THF / H2O2, NaOH</p>

BH3, THF / H2O2, NaOH

Anti-Markov. addition of H2O

<p>Anti-Markov. addition of H2O</p>
11
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<p>HBr, peroxides (ROOR)</p>

HBr, peroxides (ROOR)

Anti-Markov. addition of H and Br

<p>Anti-Markov. addition of H and Br</p>
12
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<p>HX</p>

HX

Markov. addition of H and X

<p>Markov. addition of H and X</p>
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<p>Br2, HOR</p>

Br2, HOR

Markov. addition of Br and OR (trans only)

<p>Markov. addition of Br and OR (trans only)</p>
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<p>MCPBA (or other ROOH)</p>

MCPBA (or other ROOH)

oxidization of alkene to epoxide

<p>oxidization of alkene to epoxide</p>
15
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<p>CHCl3 / KOH or CH2I2 / Zn(Cu)</p>

CHCl3 / KOH or CH2I2 / Zn(Cu)

Alkene to cyclopropane

<p>Alkene to cyclopropane</p>
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RO- / dilute acid

Anti-Markov. epoxide ring opening (basic conditions)

17
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H+, HOR

Markov. epoxide ring opening (acidic conditions)

18
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PCC

oxidize primary alcohol to aldehyde, secondary alcohol to ketone

19
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KmNO4 or Na2Cr2O7 / acid / water, CrO3 / acid / water

oxidize primary alcohol/aldehyde to carboxylic acid, secondary alcohol to ketone

20
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O3 / Zn, acetic acid

ozonolysis (oxidative cleavage of C double bond)

21
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KMnO4 (hot) / H3O+/ H2O

Permanganate (strong oxidative cleavage of C double bond)

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25
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