OCHEM 2211 Chapter 9 mechanisms

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Last updated 10:30 PM on 4/27/26
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12 Terms

1
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Hydrohalogenation

2 step process, an alkyne combining with excess HX, X being Cl, Br, or I to create a geminal halide- mark regio-selectivity and no stereo-specificity (1 HX creates a vinyl halide)

<p>2 step process, an alkyne combining with excess HX, X being Cl, Br, or I to create a geminal halide- mark regio-selectivity and no stereo-specificity (1 HX creates a vinyl halide)</p>
2
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Hydrobromination

2 step process, an alkyne combining with excess HBr and peroxide to create a geminal dihalide- anti-mark regio-selectivity and anti stereo-specificity (1 HBR creates a vinyl halide)

<p>2 step process, an alkyne combining with excess HBr and peroxide to create a geminal dihalide- anti-mark regio-selectivity and anti stereo-specificity (1 HBR creates a vinyl halide)</p>
3
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Halogenation

2 step process, an alkyne combining with excess X2, X being Cl or Br, and CCl4 to create a tetrahalide- mark regio- selectivity and anti stereo-specificity (1 X2 creates a Vicinal/trans Dihalide)

<p>2 step process, an alkyne combining with excess X2, X being Cl or Br, and CCl4 to create a tetrahalide- mark regio- selectivity and anti stereo-specificity (1 X2 creates a Vicinal/trans Dihalide) </p>
4
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Tautomerization

2 step process, an alkyne-alcohol with H3O to create a ketone or aldehyde, depending on the structure

<p>2 step process, an alkyne-alcohol with H3O to create a ketone or aldehyde, depending on the structure </p>
5
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Mercury- Catalyzed Hydration

1 step process, an alkyne with H2O, H2SO4, and HgSO4 to create an alcohol, subject to go through tautomerization- mark regio-selectivity and no stereo-specificity

<p>1 step process, an alkyne with H2O, H2SO4, and HgSO4 to create an alcohol, subject to go through tautomerization- mark regio-selectivity and no stereo-specificity</p>
6
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Alkyne formation

2 step process, an alkene with X2, X being Br or Cl, CCl4, and NaNH2 to create an alkyne

<p>2 step process, an alkene with X2, X being Br or Cl, CCl4, and NaNH2 to create an alkyne </p>
7
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Hydroboration-Oxidation

2 step process, a terminal alkyne uses R2BH/9-BBN, THF then H2O2, NaOH then tautomerization to produce an alcohol- anti-mark regio-specificity and syn stereo-selectivity

<p>2 step process, a terminal alkyne uses R2BH/9-BBN, THF then H2O2, NaOH then tautomerization to produce an alcohol- anti-mark regio-specificity and syn stereo-selectivity</p>
8
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Catalytic Hydrogenation

2 step process, an alkyne with excess H2 and a metal to create an alkane- no regio-selectivity and syn stereo-specificity

<p>2 step process, an alkyne with excess H2 and a metal to create an alkane- no regio-selectivity and syn stereo-specificity</p>
9
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Dissolving Metal Reduction

1 step process, an internal alkyne with an alkali metal and liquid NH3 to produce a trans alkene- no regio-selectivity and anti stereo-specificity

<p>1 step process, an internal alkyne with an alkali metal and liquid NH3 to produce a trans alkene- no regio-selectivity and anti stereo-specificity</p>
10
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Lindlar’s Hydrogenation

1 step process, an alkyne with H2 and Lindlar’s catalyst produces a cis alkene- no regio-selectivity and syn stereo-specificity

<p>1 step process, an alkyne with H2 and Lindlar’s catalyst produces a cis alkene- no regio-selectivity and syn stereo-specificity</p>
11
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Oxidative Ozonolysis

2 step process, an alkyne with O3 @ -78C and H2O cleaves down through the triple bond to produce a carboxylic acid (no terminal H) or CO2 (1 terminal H)- no regio-selectivity nor stereo-specificity

<p>2 step process, an alkyne with O3 @ -78C and H2O cleaves down through the triple bond to produce a carboxylic acid (no terminal H) or CO2 (1 terminal H)- no regio-selectivity nor stereo-specificity</p>
12
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Chain Extension

2 step process, a terminal alkyne with NaNH2, liquid NH3 then an alkyl halide to add said halide to the original alkyne

<p>2 step process, a terminal alkyne with NaNH2, liquid NH3 then an alkyl halide to add said halide to the original alkyne</p>