Ch 7 Alkyne Reaction Grid

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Last updated 12:36 AM on 4/30/26
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24 Terms

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<ol><li><p>NaH</p></li><li><p>CH3CH2CH2 Br</p></li></ol><p></p>

  1. NaH

  2. CH3CH2CH2 Br

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1. NaNH2

2. CH3I

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<p>HBr</p>

HBr

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<p>Br2</p><p>CH3COOH,</p><p>LiBr</p>

Br2

CH3COOH,

LiBr

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<p>1. BH3 or (sia)2BH</p><p>2. H2O2, NaOH</p>

1. BH3 or (sia)2BH

2. H2O2, NaOH

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

H2O, H2SO4,

HgSO4

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<p>H2</p><p>Lindlar</p><p>catalyst</p>

H2

Lindlar

catalyst

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<p>Na</p><p>NH3(l)</p>

Na

NH3(l)

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<p>Lengthen Terminal ONLY</p>

Lengthen Terminal ONLY

NaNH2

CH3 Br

<p>NaNH2 </p><p>CH3 Br</p>
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<p>Break triple/double bond (removes pi bonds)</p>

Break triple/double bond (removes pi bonds)

H2 + Pd

<p>H2 + Pd</p>
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<p>Half break triple → double (TRANS)</p>

Half break triple → double (TRANS)

  1. Na

  2. Li/NH3

<ol><li><p>Na </p></li><li><p>Li/NH3</p></li></ol><p></p>
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<p>Half break triple → double (CIS)</p>

Half break triple → double (CIS)

  1. H2

  2. Lindlar

<ol><li><p>H2</p></li><li><p>Lindlar</p></li></ol><p></p>
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<p>Alkene → Alkyne</p>

Alkene → Alkyne

  1. Br2

  1. NaNH2 (2x)

  2. H2O

<ol><li><p>Br2</p></li></ol><p></p><ol><li><p>NaNH2 (2x) </p></li><li><p>H2O</p></li></ol><p></p>
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<p>Addition of HX (Halogens)</p>

Addition of HX (Halogens)

HCl (2x)

<p>HCl (2x)</p>
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<p>Addition of X2</p>

Addition of X2

Br-Br (Br2)

<p>Br-Br (Br<sub>2</sub>)</p>
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<p>Hydro Boration (terminal)</p>

Hydro Boration (terminal)

  1. (Sia)2BH

  2. H2O2,NaOH

<ol><li><p>(Sia)<sub>2</sub>BH</p></li><li><p>H2O2,NaOH</p></li></ol><p></p>
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<p>Hydro Boration (internal)</p>

Hydro Boration (internal)

  1. BH3

  2. NaOH, H2O2

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<p>Acid catalyzed Hydration</p>

Acid catalyzed Hydration

HgSO4, H2SO4,H2O

<p>HgSO<sub>4</sub>, H<sub>2</sub>SO<sub>4</sub>,H<sub>2</sub>O</p>
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Chapter 8 Stuff

Chapter 8 Stuff

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<p>Light Stuff (Most Stable/Substituted)</p>

Light Stuff (Most Stable/Substituted)

  1. Br2

  2. Light/Heat

<ol><li><p>Br<sub>2</sub></p></li><li><p>Light/Heat</p></li></ol><p></p>
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<p>Allylic Position ONLY</p>

Allylic Position ONLY

  1. NBS

  2. Light

<ol><li><p>NBS</p></li><li><p>Light</p></li></ol><p></p>
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<p>radical addition of HBr to an alkene</p>

radical addition of HBr to an alkene

  1. HBr

  2. Perox

<ol><li><p>HBr</p></li><li><p>Perox</p></li></ol><p></p>
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