File Name: reactions of alkanes alkenes and alkynes .zip
In organic chemistry , an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C 2 H 2 , known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic. By virtue of this bond angle, alkynes are rod-like. Correspondingly, cyclic alkynes are rare. Benzyne cannot be isolated.
Bonding usually discussed in the context of molecular orbital theory , which recognizes the triple bond as arising from overlap of s and p orbitals. In the language of valence bond theory , the carbon atoms in an alkyne bond are sp hybridized : they each have two unhybridized p orbitals and two sp hybrid orbitals.
Overlap of an sp orbital from each atom forms one sp—sp sigma bond. Each p orbital on one atom overlaps one on the other atom, forming two pi bonds , giving a total of three bonds. The remaining sp orbital on each atom can form a sigma bond to another atom, for example to hydrogen atoms in the parent acetylene. The two sp orbitals project on opposite sides of the carbon atom. Internal alkynes feature carbon substituents on each acetylenic carbon.
Symmetrical examples include diphenylacetylene and 3-hexyne. Terminal alkynes have the formula RC 2 H. Terminal alkynes, like acetylene itself, are mildly acidic, with p K a values of around They are far more acidic than alkenes and alkanes, which have p K a values of around 40 and 50, respectively.
The acidic hydrogen on terminal alkynes can be replaced by a variety of groups resulting in halo-, silyl-, and alkoxoalkynes. The carbanions generated by deprotonation of terminal alkynes are called acetylides. In systematic chemical nomenclature , alkynes are named with the Greek prefix system without any additional letters. Examples include ethyne or octyne. In parent chains with four or more carbons, it is necessary to say where the triple bond is located. For octyne , one can either write 3-octyne or octyne when the bond starts at the third carbon.
The lowest number possible is given to the triple bond. When no superior functional groups are present, the parent chain must include the triple bond even if it is not the longest possible carbon chain in the molecule. Ethyne is commonly called by its trivial name acetylene. In chemistry, the suffix -yne is used to denote the presence of a triple bond. However, inorganic compounds featuring unsaturation in the form of triple bonds may be denoted by substitutive nomenclature with the same methods used with alkynes i.
The position of unsaturation is indicated by a numerical locant immediately preceding the "-yne" suffix, or 'locants' in the case of multiple triple bonds. Locants are chosen so that the numbers are low as possible. Sometimes a number between hyphens is inserted before it to state which atoms the triple bond is between.
This suffix arose as a collapsed form of the end of the word " acetylene ". The final "-e" disappears if it is followed by another suffix that starts with a vowel. Commercially, the dominant alkyne is acetylene itself, which is used as a fuel and a precursor to other compounds, e. Hundreds of millions of kilograms are produced annually by partial oxidation of natural gas : .
Propyne, also industrially useful, is also prepared by thermal cracking of hydrocarbons. Alkynes are prepared from 1,2- and 1,1-alkyl dihalides by double dehydrohalogenation. The reaction provides a means to generate alkynes from alkenes, which are first halogenated and then dehydrohalogenated.
For example, phenylacetylene can be generated from styrene by bromination followed by treatment of the resulting of styrene dibromide with sodium amide in ammonia : . Via the Fritsch—Buttenberg—Wiechell rearrangement , alkynes are prepared from vinyl bromides. Alkynes can be prepared from aldehydes using the Corey—Fuchs reaction and from aldehydes or ketones by the Seyferth—Gilbert homologation. Vinyl chlorides are susceptible to dehydrochlorination.
Vinyl chlorides are available from aldehydes using the reagent chloromethylene triphenylphosphorane. Featuring a reactive functional group , alkynes participate in many organic reactions. Such use was pioneered by Ralph Raphael , who in wrote the first book describing their versatility as intermediates in synthesis. Being more unsaturated than alkenes, alkynes characteristically undergo reactions that show that they are "doubly unsaturated". Alkynes are capable of adding two equivalents of H 2 , whereas an alkene adds only one equivalent.
Partial hydrogenation , stopping after the addition of only one equivalent to give the alkene , is usually more desirable since alkanes are less useful:. For more complex alkynes, the Lindlar catalyst is widely recommended to avoid formation of the alkane, for example in the conversion of phenylacetylene to styrene. Alkynes characteristically are capable of adding two equivalents of halogens and hydrogen halides. The hydroboration of alkynes gives vinylic boranes which oxidize to the corresponding aldehyde or ketone.
In the thiol-yne reaction the substrate is a thiol. Addition of hydrogen halides has long been of interest. In the presence of mercuric chloride as a catalyst , acetylene and hydrogen chloride react to give vinyl chloride. While this method has been abandoned in the West, it remains the main production method in China. The hydration reaction of acetylene gives acetaldehyde.
The reaction proceeds by formation of vinylalcohol, which undergoes tautomerizes to form the aldehyde. This reaction was once a major industrial process but it has been displaced by the Wacker process. This reaction occurs in nature, the catalyst being acetylene hydratase.
The hydration of phenylacetylene gives acetophenone ,  and the Ph 3 P AuCH 3 -catalyzed hydration of 1,8-nonadiyne to 2,8-nonanedione: .
Terminal alkyl alkynes exhibit tautomerism. Propyne exists in equilibrium with allene :. Alkynes undergo diverse cycloaddition reactions.
The Diels—Alder reaction with 1,3- dienes give 1,4-cyclohexadienes. This general reaction has been extensively developed. Electrophilic alkynes are especially effective dienophiles. The "cycloadduct" derived from the addition of alkynes to 2-pyrone eliminates carbon dioxide to give the aromatic compound.
Non-carbon reagents also undergo cyclization, e. Azide alkyne Huisgen cycloaddition to give triazoles. Cycloaddition processes involving alkynes are often catalyzed by metals, e.
Oxidative cleavage of alkynes proceeds via cycloaddition to metal oxides. Most famously, potassium permanganate converts alkynes to a pair of carboxylic acids. Terminal alkynes are readily converted to many derivatives, e.
Via the condensation with formaldehyde and acetylene is produced butynediol :  . In the Sonogashira reaction , terminal alkynes are coupled with aryl or vinyl halides. This reactivity exploits the fact that terminal alkynes are weak acids, whose typical p K a values around 25 place them between that of ammonia 35 and ethanol 16 :.
The reactions of alkynes with certain metal cations, e. Thus, few drops of diamminesilver I hydroxide Ag NH 3 2 OH reacts with terminal alkynes signaled by formation of a white precipitate of the silver acetylide. This reactivity is the basis of alkyne coupling reactions , including the Cadiot—Chodkiewicz coupling , Glaser coupling , and the Eglinton coupling : . In the Favorskii reaction and in alkynylations in general, terminal alkynes add to carbonyl compounds to give the hydroxyalkyne.
Alkynes form complexes with transition metals. Such complexes occur also in metal catalyzed reactions of alkynes such as alkyne trimerization. Terminal alkynes, including acetylene itself, react with water to give aldehydes. The transformation typically requires metal catalysts to give this anti-Markovnikov addition result. According to Ferdinand Bohlmann , the first naturally occurring acetylenic compound, dehydromatricaria ester, was isolated from an Artemisia species in In the nearly two centuries that have followed, well over a thousand naturally occurring acetylenes have been discovered and reported.
Polyynes , a subset of this class of natural products, have been isolated from a wide variety of plant species, cultures of higher fungi, bacteria, marine sponges, and corals. Some examples are cicutoxin , oenanthotoxin , and falcarinol. These compounds are highly bioactive, e. Alkynes occur in some pharmaceuticals, including the contraceptive noretynodrel. A carbon—carbon triple bond is also present in marketed drugs such as the antiretroviral Efavirenz and the antifungal Terbinafine.
Molecules called ene-diynes feature a ring containing an alkene "ene" between two alkyne groups "diyne". These compounds, e. Ene-diynes undergo rearrangement via the Bergman cyclization , generating highly reactive radical intermediates that attack DNA within the tumor. From Wikipedia, the free encyclopedia.
Acyclic hydrocarbon. Not to be confused with Alkane or Alkene. Main article: Transition metal alkyne complex. The Carbon—Carbon Triple Bond.
The Reactions of Alkanes, Alkenes, and Alkynes. In the absence of a spark or a high-intensity light source, alkanes are generally inert to chemical reactions. However, anyone who has used a match to light a gas burner, or dropped a match onto charcoal coated with lighter fluid, should recognize that alkanes burst into flame in the presence of a spark. It doesn't matter whether the starting material is the methane found in natural gas,. Once the reaction is ignited by a spark, these hydrocarbons burn to form CO 2 and H 2 O and give off between 45 and 50 kJ of energy per gram of fuel consumed. In the presence of light, or at high temperatures, alkanes react with halogens to form alkyl halides. Reaction with chlorine gives an alkyl chloride.
Halogens, especially chlorine and bromine add on alkenes readily producing a dihalogen derivatives. Acidity of Alkynes. Alkanes and alkenes physical properties and chemical properties Find answers and explanations to over 1. When the skeleton chain electrons of the alkane are randomly occupied by other heteroatoms, the original name is modified with the heteroatom prefix but the total number of heteroato… The carbon Laboratory Properties of Alkanes, Alkenes, and Alkynes B.
All the carbon atoms are sp3 hybridized. C-C Bond length is 1. The bond angle is Corey and Herbert House in s. Lithium dialkyl copper and an alkyl halide on reaction gives alkanes. Insoluble in polar solvents like water. Densities of alkanes are around 0.
How Can an Alkene Be Reduced to an Alkane? How Can an Acetylide Anion Be Used to Create a New Carbon–Carbon Bond?
Choose the best answer for the following questions. For each question there is one correct answer. Multiple Choice. E lack of rotation of the double bond.
The largest database 1 of organic compounds lists about 10 million substances, which include compounds originating from living organisms and those synthesized by chemists. The number of potential organic compounds has been estimated 2 at 10 60 —an astronomically high number.
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