Integrated SequencePhysics Chemistry Organic Biology

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Module 9 in the Syllabus

Alkynes Mechanisms
Mechanisms and explanations from the Organic Mechanisms Pocketbook

Reactions of Alkynes Images
Image gallery for study with links to larger teaching JPEGs for classroom presentation

Question Drill for Reactions of Alkynes
Conceptual Vocabulary Self-Test

Basic Terms Crossword Puzzle

Basic Puzzle Solution

Conceptual Vocabulary
AlkyneAlkynes are hydrocarbons that have at least one triple bond between two carbon atoms.
AcetyleneAcetylene is a hydrocarbon belonging to the group of alkynes, considered to be the simplest of all alkynes as it consists of two hydrogen atoms and two carbon atoms.
CycloalkyneA cycloalkyne is a hydrocarbon which is the cyclic analog of an alkyne.
Metal acetylideA metal acetylide is an alkyne for which the terminal proton has been replaced by a metal such as sodium or an organolithium.
EnyneAn enyne is a functional group in organic chemistry consisting of a conjugated alkyne and alkene group.
HydroaminationThe hydroamination reaction is the addition a nitrogen-hydrogen bond across the carbon-carbon double or triple bonds of an alkene or alkyne.
Lindlar catalystUsed for the hydrogenation of alkynes to alkenes, the Lindlar catalyst is a heterogeneous catalyst that consists of palladium deposited on calcium carbonate and treated with various forms of lead.
Coupling reactionA coupling reaction is a catch-all for a range of reactions in organometallic chemistry where two hydrocarbon radicals are coupled with the aid of a metal containing catalyst.
Alkyne trimerisationAn alkyne trimerisation reaction is a 2+2+2 cyclization reaction where three alkyne molecules react to form a benzene compound.
Alkyne metathesisAlkyne metathesis is an organic reaction involving the redistribution of alkyne chemical bonds.
Alkyne zipper reactionThe alkyne zipper reaction is a reaction which isomerizes an organic compound containing an internal alkyne into a terminal alkyne.
Enyne metathesisAn enyne metathesis is an organic reaction taking place between an alkyne and an alkene with a metal carbene catalyst forming a butadiene.
Advanced terms that may appear in context in MCAT passages
Sonogashira couplingA Sonogashira coupling is a coupling reaction of terminal alkynes with aryl or vinyl halides.
Bergman cyclizationThe Bergman cyclization is an organic reaction and more specifically a rearrangement reaction taking place when an enyne is heated in presence of a suitable hydrogen donor.
Azide alkyne Huisgen cycloadditionThe Azide-Alkyne Huisgen Cycloaddition is a 1,3-dipolar cycloaddition between an azide and a terminal or internal alkyne to give a 1,2,3-triazole.
Cadiot-Chodkiewicz couplingThe Cadiot-Chodkiewicz coupling in organic chemistry is a coupling reaction between a terminal alkyne and a haloalkyne catalyzed by a copper(I) salt such as copper(I) bromide and an amine base.
Favorskii reactionThe Favorskii reaction (not to be confused with the rearrangement of the same name) is a special case of nucleophilic attack on a carbonyl group involving a terminal alkyne with acidic protons.

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