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Reaction of Alkenes and Alkynes For Students
Reaction of Alkenes and Alkynes For Students
Alkenes
Addition to carbon-carbon double bond MECHANISM Double bond is broken and in its place single bonds form to two new atoms or groups of atoms.
Addition Reactions
Hydrohalogenation Hydration Bromination Hydrogenation (reduction)
Addition Reaction
Hydrogenation
The reaction is carried out under pressure at a temperature of 200 C in the presence of a metallic catalyst. Common industrial catalysts are based on platinum, nickel or palladium. For laboratory syntheses, Raney nickel (an alloy of nickel and aluminium) is often employed.
Hydrogenation
Halogenation
Hydrohalogenation
Reactions of hydrogen halides (HX) with alkenes produces haloalkanes (alkyl halide) Some reactions proceeds to regioselectivity
Regioselectivity
Was first noted by Vladimir Markovnikov Regioselective reaction takes place when one direction of bond forming or breaking occurs in preference to all other directions. The Markovnikovs Rule
Markovnikovs Rule
In the addition of HX to an alkene, hydrogen adds to the doubly bonded carbon that has greater number of hydrogens already bonded to it; halogen adds to the other carbon.
Hydration
Addition of Water: Acid-catalyzed hydration In the presence of an acid catalyst, most commonly conc. H2SO4, water adds to the carbon-carbon double bond to give an alcohol.
Hydration
In simple alkenes, hydration follows the Markovnikovs rule. That is, H adds to the carbon of the double bond with the greater number of hydrogens and OH adds to the carbon with the smaller number of hydrogens.
Halogenation
Addition of bromine and chlorine Br2 and Cl2 react with alkenes at room temperature by addition of halogen atoms to the carbon atoms of the double bonds
Halogenation
Generally carried out either by using pure reagents or by mixing them in an inert solvent, such as dichloromethane, CH2Cl2.
Importance
Useful qualitative test for the presence of an alkene. How?: Br2 in CCl4 (red to brown) is mixed with a suspected alkene, the disappearance of the red color means that the bromine was added to the double bond.
Hydrogenation
Addition of Hydrogen All alkenes react quantitatively with H2 in the presence of a transition metal catalyst to give alkanes. Catalysts used are platinum, palladium, ruthenium and nickel.
Hydrogenation
It involves reduction by hydrogen in the presence of a catalyst, thus; it is also called as the catalytic reduction or catalytic hydrogenation.
Hydrogenation
Catalyst finely powdered solid Carried out by dissolving alkene in ethanol or other non-reactive organic solvent, adding the catalyst, and exposing the mixture to hydrogen gas at pressures ranging from 1 to 150 atm.
Polymerization
Formation of chain-growth polymers Most important reaction of alkenes With the presence of initiators, many alkenes form polymers
Polymerization
Low-density Polyethylene (LDPE) Transparent polymer from the ethylene polymerization with peroxide as initiator Highly branched Do not pack well together London dispersion forces are weak
Polymerization
High-density Polyethylene (HDPE) Does not rely on peroxide initiators Developed by Karl Ziegler and Guilio Natta Little chain branching Chains are pack together more closely Stronger london dispersion forces
In answer to the objections to the structure proposed by Kekul, resonance hybrid of the molecular benzene was used.
Experimentally, the length of the carboncarbon bond in benzene is not as long as a C-C nor as short as a C=C, but rather midway between the two.
The closed loop of six electrons ( two from the second bond of each double bond) characteristic of a benzene ring is sometimes called an aromatic sextet.
The benzene ring is greatly stabilized by resonance, which explains why it does not undergo the addition reactions of typical alkenes.
Halogenation
Cl2 and Br2 noramlly do not react with benzene but with an Fe catalyst, halogens reacts rapidly to give halobenzene and HCl.
Sample
Chlorination of benzene in FeCl3 Bromination of benzene in FeCl3
Nitration
Heating benzene or its derivative with conc. nitric acid, one of the hydrogen atoms bonded to the ring is replaced by a nitro (-NO2) group.
Sample
Nitration of benzene Nitration of toluene
Sulfonation
Heating an aromatic compound with conc. sulfuric acid results in the formation of an arenesulfonic acid and water. Major use is in the preparation of synthetic detergents
PHENOLS
The functional group of phenols is a hydroxy group bonded to a benzene ring Subtituted phenols are named either as derivatives of phenols or by common names.
Sample
Phenol 3-methylphenol (m-cresol) 1,2-benzenediol
Sources
Widely distributed in nature Phenol and the isomeric cresol (o-, m-, and p-) are found in coal tar. Thymol and vanillin are important constituents of thyme and vanilla beans. Urushiol is the main component of poison ivy an irritating oil