Reagents

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Last updated 7:32 PM on 4/24/26
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38 Terms

1
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alkene —> alkyl halide

H-X (markovnikov)

H-Br, ROOR (anti-markivnikov)

2
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Alkene —> alcohol / Markovnikov / acid-cat

  1. dil. H2SO4

  2. H2O

(or H3O + only)

3
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Find the second reagent

  1. dil H2SO4

H2O

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Alcohol —> alkene +H2O

  1. conc. H2SO4

  2. Heat

5
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Alkene —> Alcohol (markovnikov) / Oxymercuratio-Demercuration

  1. Hg(OAC)2 , H2O

  2. NaBH4

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Complete the reagents

  1. Hg(OAC)2

H2O

NaBH4

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Alkene —> alcohol (anti-markovnikov) / Hydroboration

  1. BH3 THF

  2. H2O2, NaOH

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Complete the reagents

  1. BH3 THF

  1. H2O2 , NaOH

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Alkene —> Alkane (syn addition)

  1. H2, Pd or H2, Pt

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Alkene —> alkyl dihalide (ANTI-Addition)

  1. Br2

  2. CCl4 or CHCl3 or CH2Cl2

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Complete reagents

  1. Br2

  1. CCl4

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Alkene —> Halohydrin (OH+X) (Markovnikov -- OH to most sub.)

  1. Br2

  2. H2O

(if CH3OH given the alkane will have Br + OCH3)

13
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Anti-dihydroxylation

  1. mCPBA or RCO3H

  2. H3O+

14
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Complete reagents

  1. mCPBA

  1. H3O+

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Syn-Dihydroxylation

  1. OsO4

  2. NaHSO3

or

  1. KMnO4, cold

  2. NaOH

16
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Complete

  1. OsO4

2.NaHSO3

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Complete

  1. KMnO4

  1. NaOH

  2. Cold

18
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oxidative cleavage (alkenes)

  1. O3

  2. DMS

19
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Complete

  1. O3

  1. DMS

20
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Alkyne —> Alkene —> Alkane

  1. H2,Pt

or to alkane

  1. xs H2, Pt

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Alkyne —> cis alkene

  1. H2

  2. Lindlar's catalyst or P-2 (Ni2B)

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Complete (cis alkene)

  1. H2

  1. Lindlar's catalyst

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Alkyne —> trans alkene

  1. Na

  2. NH3 (l)

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Complete (trans)

  1. Na (s)

  1. NH3 (l)

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Deprotonating Alkynes

NaH

NaNH2

BuLi

LDA

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Dihalide —> alkyne

1.xs NaNH2

2.H2O

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Complete (do not form an ion)

  1. xs NaNH2

2.H2O

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terminal alkyne —> Ketone

  1. HgSO4

  2. H2SO4

  3. H2O

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Complete terminal alkyne —> ketone

  1. HgSO4

2.H2SO4

3.H2O

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Terminal alkyne —> Aldehyde (Anti-markovnikov)

  1. BH3THF (9-BBN)

  2. H2O2

  3. NaOH

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Complete alkyne —> Aldehyde

  1. 9-BBN

2.H2O2

3.NaOH

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If internal alkyne reatc with 9-BBN , H2O2, NaOH

Ketone

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Alkyne —> tetrahalides

  1. xs X2

  2. CCl4

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Internal alkyne —> 2 carboxylic acids

  1. O3

  2. H2O

35
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COmplete (form 2 -COOH)

  1. O3

  1. H2O

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Terminal alkyne —> 1 carboxylic acid + CO2

  1. O3

  2. H2O

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Complete to form 1 -COOH + CO2

  1. O3

  2. H2O

38
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