Organic Chemistry (Chapter 13: Alkynes)

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19 Terms

1

Nomenclature of Alkynes

  1. Number the carbons in a way that the carbon-carbon triple bond has the lowest priority numbers

  2. Name the substituents and note their location

    • methyl group on carbon number 5

  3. Name parent chain of the molecule including the location of the triple bond

    • hexane to hexyne

    • location of the triple bond starts on the first carbon

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2

Special nomenclature example

  • for this example it has a cyclic and a straight chain component

  • when naming the longest carbon chain it is either EXCLUSIVELY the ring or the straight chain

    • NO mix and match

  • since we are prioritizing the alkyne you want to name the longest carbon chain down in the straight chain

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3
<p>Priority: Highest to Lowest</p>

Priority: Highest to Lowest

Numbering begins closest to the highest priority group

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4
<p>The Reactivity of Alkynes</p>

The Reactivity of Alkynes

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5
<p>Relative Stabilities of Carbocations</p>

Relative Stabilities of Carbocations

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6
<p>Addition of H-X to an Alkyne</p>

Addition of H-X to an Alkyne

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7
<p>Addition of EXCESS H-X to an alkyne</p>

Addition of EXCESS H-X to an alkyne

In the presence of excess H-X the reaction proceeds to a geminal dihalide

<p>In the presence of excess H-X the reaction proceeds to a geminal dihalide</p>
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8
<p>Addition of H-X to an unsymmetrical internal alkyne</p>

Addition of H-X to an unsymmetrical internal alkyne

If the internal alkyne is SYMMETRICAL only one product is formed

<p>If the internal alkyne is SYMMETRICAL only one product is formed</p>
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9
<p>The Addition of X2 to Alkynes</p>

The Addition of X2 to Alkynes

Proposed mechanism: analogous to the addition of X2 to alkenes (X2=Cl2, Br2,I2)

<p>Proposed mechanism: analogous to the addition of X2 to alkenes (X<sub>2</sub>=Cl<sub>2</sub>, Br<sub>2</sub>,I<sub>2</sub>)</p>
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10
<p>The Addition of water to an Alkyne</p>

The Addition of water to an Alkyne

tautomerization is apart of the process

<p>tautomerization is apart of the process </p>
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11
<p>The Addition of Borane to an Alkyne (internal alkynes)</p>

The Addition of Borane to an Alkyne (internal alkynes)

The hybridization-oxidation of internal alkynes occurs in an analogous way to the hydroboration-oxidation of alkenes:

<p>The hybridization-oxidation of internal alkynes occurs in an analogous way to the hydroboration-oxidation of alkenes:</p>
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12
<p>The Addition of Borane to an Alkyne (terminal alkynes)</p>

The Addition of Borane to an Alkyne (terminal alkynes)

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13
<p>Two Methods to Hydrate an Alkyne</p>

Two Methods to Hydrate an Alkyne

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14
<p>The Addition of Hydrogen to an Alkyne</p>

The Addition of Hydrogen to an Alkyne

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15
<p>The Addition of Hydrogen to an Alkyne (Alternative=lindlar catalyst)</p>

The Addition of Hydrogen to an Alkyne (Alternative=lindlar catalyst)

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16
<p>How can you obtain a trans alkene from partial reduction of alkynes</p>

How can you obtain a trans alkene from partial reduction of alkynes

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17
<p>Synthesis using Acetylide Ions</p>

Synthesis using Acetylide Ions

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18
<p>Synthesis (Example#1)</p>

Synthesis (Example#1)

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19
<p>Synthesis (Example#2)</p>

Synthesis (Example#2)

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