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22 Cards in this Set

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define an alkyne
a hydrocarbon with a triple bond.
what is the simplest alkyne?
Acetylene H-C///C-H
A C-C trible bond results from the interaction of ____ ?
two sp hybrid oritals of carbon lying 180 degrees from each other along an axis of two unhybridized 2py and 2pz orbitals
how is the length of a triple bond related to its strength?
the triple bond is the shortest and therefore strongest known Carbon-Carbon bond
Explain why the triple bond is linear
two sp-hybridized carbons approach each other, and this forms one sp-sp sigma bond and two p-p pi bonds. that leaves only two remaining sp orbitals to form bonds to other atoms at a 180 degree angle.
Naming

begin numbering at...
the end nearer the triple bond so that the triple bond receives as low a number as possible
compounds with more than one triple bond are called...
diynes, triyes, and so forth
compounds with double and triple bonds are called ___
enynes
numbering of an eyne chain starts from the end....
nearer the first multiple bond, whether double or triple. but double bonds receive lower numbers than triple bonds
just as there are alkyl groups derived from alkanes, and alkenyl substituents from alkenes, there are ____ groups from alkynes
alkynyl
alkynes can be prepared y _________ from alkyl halides in much the same manner as alkenes
elimination of HX
what does "vicinal" mean?
it's a term used to refer to a 1,2 di- substitution pattern.
give an example of a vicinal molecule
1,2 dibromoethane is a vicinal dibromide.
Treatment of ______ with excess _____ results in _______ and formation of an alkyne.
Treatment of a 1,2-dihaloalkane with excess strong base such as KOH or NaNH2 results in a twofold elimination of HX and fomration of an alkyne.
how can you obtain the necessary vicinal dehalides for the formation of an alkyne? what is the significance of this?
they are readily available by addition of Br2 or Cl2 to alkenes. This means that the overall halogenation/dehydrohalogenation sequence gies a way to go from an alkene to an alkyne
what is a vinylic subsituent?
one that is attached to a double-bond carbon.
what does the twofold dehydrohalogenation take place through?
a vinylic halide intermediate.
which gets priority in naming: a double or a triple bond?
double
Alkynes react with HBR and HCl to yield....
*vinylic* halides
Alkynes react with Br2 and Cl2 to yield...
1,2 dihalides (vicinal dihalides)
Alkynes can be hydrated by reation with ____ in the presence of ____
aqueous sulfuric acid in the presence of mercury (11) catalyst.
Alkyne hydration reaction with aqueous sulfuric acid in the presence of mercury(11) catalyst leads to an intermediate _____ that immediately isomerizes to yield a ketone _______
intermediate enol
ketone tautomer
...a methyl ketone is producedfrom a terminal alkyne