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| a carbon-carbon triple bond functional group |
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| What is the common name of the smallest alkyne, C2H2 |
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| In IUPAC nomenclature for alkynes, the rules for naming alkenes also apply, except the ending _____ replaces the ending "-ene" |
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| alkynes having the general structure: RC(triple bond)CH |
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| alkynes having the general structure: RC(triple bond)CR' |
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| substituents bearing a triple bond |
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| in IUPAC nomenclature, a hydrocarbon containing both double & triple bonds |
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| When a double bond and a triple bond are equidistant from either terminus, the _____ bond is given the lower number |
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| alkynes incorporation the hydroxy function |
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| The _____ group takes precedence over both double & triple bonds in the numbering of a chain |
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| Strong bases such as sodium amide in liquid ammonia, alkyllithiums, & Grignard reagents can deprotonate terminal alkynes to the corresponding _____ |
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| halogenation-double dehydrohalogenation |
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Definition
a means of converting alkenes into the corresponding alkynes;
1. add halogen
2. add NaNH2, liquid NH3
3. add H2O |
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| Although mixtures of E- and Z-haloalkenes are in principle possible, with diastereomerically pure vicinal dihaloalkanes only one product is formed because elimination proceeds stereospecifically _____ |
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Definition
| a modified catalyst that stops alkyne hydrogenation at the intermediate alkene stage |
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| As with the catalytic hydrogenation of alkenes, the addition of H2 is a _____ process |
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| When we use _____ dissolved in liquid ammonia as the reagent for the reduction of alkynes, we obtain trans alkenes as the products |
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Definition
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| dissolving-metal reduction |
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Definition
| using sodium metal dissolved in liquid ammonia to reduce an alkyne to obtain the trans alkene |
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| Dissolving-metal reduction is a _____ process |
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| The stereochemistry of addition of a hydrogen halide to an internal alkene is typically _____, particularly when excess halide ion is used |
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Definition
| addition of a second molecule of H-X giving the product with both X atoms bound to the same carbon |
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| Electrophilic addition of halogen to alkynes proceeds through the intermediacy of isolable vicinal dihaloalkanes, the products of a single _____ addition |
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Definition
| the alcohol product when water is added to alkynes in a Markovnikov sense; the hydroxy group is attached to a double-bonded carbon |
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| the process of enols spontaneously rearranging to the isomeric carbonyl compound; interconverts two isomers by simultaneous proton & double-bond shifts |
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Definition
| the process of going from an enol to a carbonyl compound |
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| the enol & carbonyl species |
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| As with alkenes, hydrogen bromide can add to triple bonds and both _____ & _____ additions are observed |
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Definition
| in the presence of soluble complexes of metals such as Ni & Pd, alkenyl halides undergo carbon-carbon bond formation with alkenes to produce dienes; a molecule of hydrogen halide is liberated |
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| 4 step mechanism for the Heck reaction |
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Definition
1. attack of the metal on the alkenyl halide to give the alkenylmetal halide
2. the alkene then complexes with the metal
3. the alkene inserts itself into the carbon-metal bond, forming the new carbon-carbon linkage
4. elimination of HX in an E2-like manner gives the diene product & frees the metal catalyst |
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