Synthetic Transformations

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25 Terms

1

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Addition of H and OH without rearrangement reagents

Hg(OAc₂), H₂O, THF
NaBH₄

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Anti-Markovnikov Addition of H and OH Reagents

BH₃, THF
H₂O₂, NaOH, H₂O

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Anti-Markovnikov addition of H and Br Reagents

HBr, ROOR, Heat

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Markovnikov addition of H and X Reagents

HX, Cold and dark

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<p>Oxidation of an Alkene to an Epoxide reagents</p>

Oxidation of an Alkene to an Epoxide reagents

MCPBA

<p>MCPBA</p>

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<p>Anti-Markovnikov Epoxide Ring Opening (basic) reagents</p>

Anti-Markovnikov Epoxide Ring Opening (basic) reagents

strong base
dilute acid

<ol><li><p>strong base</p></li><li><p>dilute acid</p></li></ol><p></p>

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<p>Markovnikov Epoxide Ring Opening (acidic) Reagents</p>

Markovnikov Epoxide Ring Opening (acidic) Reagents

H⁺, HOR

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<p>Markovnikov Addition of Br and OR to an alkene</p>

Markovnikov Addition of Br and OR to an alkene

Br₂, HOR

<p>Br<sub>2</sub>, HOR</p>

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<p>Cyclopropane Ring from an Alkene</p>

Cyclopropane Ring from an Alkene

CHCl₃, KOH (forms carbene)

<p>CHCl<sub>3</sub>, KOH (forms carbene)</p>

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<p>Catalytic Hydrogenation</p>

Catalytic Hydrogenation

H₂ Pd/C

<p>H<sub>2</sub> Pd/C</p>

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<p>Selective Catalytic Hydrogenation of Alkyne (2 pathways)</p>

Selective Catalytic Hydrogenation of Alkyne (2 pathways)

H₂ with Lindlar or Ni₂B

<p>H<sub>2</sub> with Lindlar or Ni<sub>2</sub>B</p>

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Trans-addition of H₂

Na, NH₃

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<p>Oxidation of a 1º Alcohol to an Aldehyde</p>

Oxidation of a 1º Alcohol to an Aldehyde

PCC

<p>PCC</p>

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<p>Oxidation of 2º Alcohol to a Ketone (4 pathways)</p>

Oxidation of 2º Alcohol to a Ketone (4 pathways)

KMnO₄, Na₂Cr₂O₇/acid/water, CrO₃/acid/water, PCC

<p>KMnO<sub>4</sub>, Na<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>/acid/water, CrO<sub>3</sub>/acid/water, PCC</p>

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<p>Oxidation of a 1º Alcohol or Aldehyde to a Carboxylic Acid</p>

Oxidation of a 1º Alcohol or Aldehyde to a Carboxylic Acid

KMnO₄, Na₂Cr₂O₇/acid/water, CrO₃/acid/water

<p>KMnO<sub>4</sub>, Na<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>/acid/water, CrO<sub>3</sub>/acid/water</p>

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<p>Syn Addition of Two OH Groups to a pi Bond</p>

Syn Addition of Two OH Groups to a pi Bond

OsO₄
H₂O₂/NaHSO₃

<ol><li><p> OsO<sub>4</sub></p></li><li><p>H<sub>2</sub>O<sub>2</sub>/NaHSO<sub>3</sub></p></li></ol><p></p>

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<p><span>Cleavage of a C=C Double Bond using Ozone (Ozonolysis)</span></p>

Cleavage of a C=C Double Bond using Ozone (Ozonolysis)

O₃
Zn, acetic acid

<ol><li><p>O<sub>3</sub></p></li><li><p>Zn, acetic acid</p></li></ol><p></p>

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<p><span>Cleavage of a C=C Double Bond using Permaganate</span></p>

Cleavage of a C=C Double Bond using Permaganate

KMnO₄ (hot)
H₃O⁺/H₂O

<ol><li><p>KMnO<sub>4</sub> (hot)</p></li><li><p>H<sub>3</sub>O<sup>+</sup>/H<sub>2</sub>O</p></li></ol><p></p>

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<p><span>Markov. Addition of H 2O to an Alkyne</span></p>

Markov. Addition of H 2O to an Alkyne

H₂O, H₂SO₄, HgSO₄

<p>H<sub>2</sub>O, H<sub>2</sub>SO<sub>4</sub>, HgSO<sub>4</sub></p>

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Anti-Markov. Addition of H₂O to an Alkyne

BH₃ THF
H2O2, NaOH, H2O

<ol><li><p>BH<sub>3</sub> THF</p></li><li><p>H2O2, NaOH, H2O</p></li></ol><p></p>

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<p>Deprotonation of an Alkyne</p>

Deprotonation of an Alkyne

NaNH2

<p>NaNH2</p>

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<p>Nitrile Hydrolysis</p>

Nitrile Hydrolysis

H2O H2SO4

<p>H2O H2SO4</p>

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<p>Halogenation of an alcohol (acid)</p>

Halogenation of an alcohol (acid)

HX

<p>HX</p>

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<p>Chlorination of an alcohol</p>

Chlorination of an alcohol

SOCl2

<p>SOCl2</p>

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