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Alkanes - Organic Chemistry Tutor

This is the correct chemical term for compounds known as paraffins. They are considered the simplest organic compounds and are a family of chain hydrocarbons having the general formula C2 H2n+2. All of the bonds are single bonds (-C-H-, and -C-C-). The chains can be straight or branched. The smaller members (less than 4 carbons) are gases, while larger ones (five to seventeen carbons) are liquids. Beyond seventeen carbons the alkanes are waxy solids.

Structure
The simplest saturated acyclic hydrocarbon is methane, CH4. The other hydrocarbons belonging to this class can be taken as descendents of methane, resulted from the substitution of one or more atoms of hydrogen with hydrocarbon radicals. Therefore, if one hydrogen atom from methane is replaced by a methyl radical, -CH3, the hydrocarbon (superior to methane) will have the composition C2 H6, named ethane. If one hydrogen atom is replaced by a methyl radical -CH3, the saturated hydrocarbon obtained (-C3 H8) will be named propane: CH3 -CH2 -CH3. Propane is also considered as the derivation of methane resulted by the replacement of two hydrogen atoms with two methyl radicals or with one ethyl radical (-C2H5 ). If you continue the successive substitution of one hydrogen atom with from the hydrocarbon with one radical CH3 you will obtain a series of hydrocarbons, each different from one another with one group of CH2 : Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decan CH4 CH3-CH3 CH3-CH2 -CH3 CH3-CH2 -CH2-CH3 CH3-CH2-CH2-CH2 -CH3 CH3-CH2 -CH2-CH2-CH2-CH3 CH3-CH2 -CH2-CH2-CH2-CH2 -CH3 CH3-CH2 -CH2-CH2-CH2-CH2 -CH2-CH3 CH3-CH2-CH2-CH2-CH2 -CH2 -CH2-CH2 -CH3 CH3-CH2 -CH2-CH2-CH2-CH2 -CH2-CH2 -CH2 -CH3

Such a series, where every last term of the line differs from the former through a CH2 group is named homologous series. Each term of this series is the superior homologue of the previous one. The chemical structure of the chain of the homologous series terms, meaning of the homologues, is identical. Therefore, the chemical properties of the homologues are very similar. The alkanes can be: with a continuous chain, if all the carbon atoms are bound with at most two other carbon atoms, and with a branched chain, if one or more carbon atoms from the molecule are bound with at least two other carbon atoms. Such an isomerism of chain is possible starting with butane. The number of isomers of saturated acyclic hydrocarbons is very big; he grows with each number of carbon atoms from the molecule. For example, the carbide C10H22 has 75 isomers; the hydrocarbon C20H42 can have approximately 366.319 isomers.

Nomenclature
The first four alkanes with a unbranched chain, meaning normal (n-alkanes) are called: methane, ethane, propane, butane. The superior alkanes names are compound with a numeric prefix (which shows the number of carbon atoms present in the molecule) and the ending ane. For example: pentane, hexane, heptane, and octane. For the hydrocarbons with two groups of methyl (-CH3) at the end of a linear chain, you use the prefix iso- at the name of the hydrocarbon, and for those containing three -CH3 groups at the end of the chain, you use the prefix neo- at the name of the hydrocarbon. Mono valence radicals derived from normal alkanes by removing one hydrogen atom from a terminal carbon atom are called normal alkyls. Their name is formed by the replacement of the ending -ane from the hydrocarbons name with the ending -yl. For example, CH3 is called methyl; CH3-CH2 is called ethyl and CH3-CH2-CH2 is called propyl. The branched chain alkanes use the name of the longest sidewise chain as a prefix in their denomination. The position of the sidewise chain is indicated by a number. For this, the longest chain is numbered from left to right or vice verse, in the direction in which the sidewise chain will have the position with the smallest number. The presence of more identical sidewise chains is indicated by the prefixes: di-, tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-. Bivalence and tri-valence radicals derived from alkyls by removing one or two hydrogen atoms from the mono-valence carbon atom, have their names formed by adding the ending iden or -idin. For example, CH3-CH= is called ethyliden. The radical CH2= is named methylene, CH is name ethylidin.

General formula
In a alkane molecule at n carbon atoms you fin 2n+2 hydrogen atoms. Therefore the general formula of the alkanes is CnH2n+2. Relying on the general formula you can obtain the molecular formula of each and every alkane if the number of carbon atoms is known. For example, for a molecule which contains 2 carbon atoms (n=2), the number of hydrogen atoms is 2*2+2=6 so the hydrocarbons molecular formula is C2H6 (ethane).

Alkanes in nature
Some alkanes form through the slow decomposition of organic substances, especially wood, lignite and mineral coal. Therefore, they can be found in the distillery tars of these substances. Big quantities of alkanes can be found in mineral oil and natural gases. Hence, paraffin in mineral oil is a mixture of superior alkanes. Alkanes with a bigger number of carbon atoms are found in some plants. The extraction of the alkanes in pure state out of natural product is difficult, their properties being very much alike and their boiling point very close.

Obtaining methods

1. From aluminium chloride:

Al4C3 + 12H2 0 Al4C3 + 12HCl

3CH4 + 4Al(OH)3 3CH4 + 4AlCl3

2. Unsaturated hydrocarbons (which contain a double or triple bound) alkenes + H2 alkanes (addition reaction) nickel is used as a catalyser

3. From halogenated derivates: The Wurtz reaction: R-X + R-X + 2Na alkane) X can be: Cl, Br, I R-X + Mg RMgX 2NaX + R-R (the obtained alkane is a symmetrical

4. Carboxylic acids: R-COOH + NaOH H2 O + R-COONa (sodium carboxyl) Na2CO3 + R-H (alkaline melt)

5. The Kolbe electrolyze Kolbe of sodium carboxyls: R-COONa RCOO + Na H20 H + OH cathode(-) H + 1e anode(+) RCOO -1e 2RCOONa + 2H2 0 H (reduction); H20 RCOO H + OH R-R (symmetrical alkane)

R + CO2; R + R

R-R + 2CO2 + H2 + 2NaOH

Chemical reactions

1. Halogenated (Cl2, Br2) R-X + X2 R-X + HX (the obtained product is a halogenated derivate) CH3 -Cl + HCl (methyl chloride or methane chlorine)

Example: CH4 + Cl2

2. Thermic decomposition (< 650 grade - cracking; > 650 grade pyrolize) CnH2n+2 CmH2m+2 + CpH2p where n = m + p and p >= 2 CH CH + 3H2

Pyrolize methane: 2CH4 3. Alkanes isomerism

It takes place in the presence of AlCl3 at temperature within 50 and 100 Celsius degrees. The isomerism reaction is a reversible. 4. Oxidation a) Combustion: C nH2n+2 + O2 CO2 + H2 O + Q exothermic reaction dH < 0 R-CH2-OH + R-CH=O + RCOOH CO +

b) Incomplete oxidation: R-CH3 + O2 c) CH4 Oxidation: CH4 + O2 2H2 0 (incomplete combustion) 5. Nitrating reaction R-H + HNO3

CH3 -O-H (methylic alcohol); CH4 + 3/2 O2

R-NO2 + H2 O (nitro derivate)

Examples: CH4 + HNO3 CH3 -NO2 + H2O (nitro methane) CH3 -CH2 -CH3 + HNO3 CH3-CH2 -CH2 -NO2 + H20 (1-nitropropan)

Use
alkanes can be taken as fuel alkanes are used to obtain chemical compounds for different uses methyl chloride is a frigorific agent prussic acid is used to obtain synthetic fiber

Alkenes - Organic Chemistry Tutor


Acyclic hydrocarbons containing a double bound within two carbon atoms in the molecule are named alkenes. They are also called olefins, because of the fact that the chlorate and bromate derivates are oleaginous liquids.

Structure
The simplest alkene is ethylene (C2 H4), which has the International Union of Pure and Applied Chemistry name ethene. This substance contains two carbon atoms connected through a double bound. Superior alkenes can be considered as the result of the substitution of a hydrogen atom with alkyl radicals, same as the case of saturated acyclic hydrocarbons. Hence, the superior homologue of ethylene is propene, CH2=CH-CH3. The homologue of propene is buthene, C4 H8. After the position of the double bound in the molecule at buthene, you can distingiush three position isomers.

Nomenclature
By replacing the ending ane from the alkanes name with the same number of carbon atoms in the molecule with the ending ene, you obtain the alkenes name. For example: CH3 -CH2 -CH2-CH=CH-CH3 - 2 hexene So, the three position isomers of buthene are: 1-buthene, 2-buthene and 2-methylpropene. Sometimes there can be used the position of the double bound after the name of the hydrocarbon. For example: buthene-1. Alkenes mono-valence derivates have their names ending in enyl, the position of the double bound being indicated, if necessary, by a number. Exceptions: Vinyl for ethenyl: CH2=CHAlyl for 2-propenyl: CH2 -CH-CH2 Isopropenyl for 1 methyl vinyl: CH2 -C-CH3

General formula
Because of the double bound in the molecule, alkenes have two hydrogen atoms less then other saturated hydrocarbons; therefore, the general formula for these hydrocarbons is CnH2n. You can observe the homologous series of the cycloalkanes. They are, consequently, raw formula isomers.

Physical properties
C2-C4 alkenes are gases, C5-C18 are liquids and the ones with more than 18 carbon atoms are solids. The boiling points are a little bit lower than the corresponding alkanes. Their density is higher than the corresponding alkenes, but all alkenes have the density smaller than 1. Alkenes are insoluble in water, but mixable with organic solvents.

Isomerism
Alkenes present three types of isomerism: chain isomers (the isomers differ by chain), position isomers (the chain is identical but the position of the double bound differs) and function isomers. Geometrical isomerism appears at alkenes because the double bound is stiff and doesnt allow the rotation of the carbon atoms around it. Geometrical isomers are different from one another through the spatial position of the substitutes around the double bound. The condition of isomerism is that for each carbon atom from the double bound to exist a different substitute. The nomenclature of geometrical isomers: it is established by the priorities of the substitutes bind with each carbon atom from the double bound: you will compare the Z of the atoms directly connected with the carbon atom out of the double bound. The one with the biggest Z will have highest priority and it will be note with 1 and the other one, with 2. If the Zs are the same, the next pair will be compared. The comparison will be made until there appears a difference. This procedure will be applied at each carbon atom in the double bound. After establishing the priorities, the denomination will be made like this: the isomer with the substitutes on the same side of the double bound will be noted with Z (CIS) and the other, with the substitutes on one side and another of the double bound, will be noted with E (TRANS). For example: C4H8 has 6 isomers: 1-buthene, CIS 2-buthene, TRANS 2-buthene, isobutene, cyclo butene, methylcyclopropene.

Obtaining methods

1. Thermic decomposing CnH2n+2 CnH2n+2 CmH2m+2 + CpH2p - cracking; n = m + p, p >= 2 CnH2n + H2 - dehydrogenating

2. Alkynes hydrogenating R-C C-R' + H2 R-CH=CH-R (alkyne) the reaction takes place in the presence of Pd poisoned with Pb salt Examples: CH CH + H2 CH2=CH2 (ethane) CH3 -C CH + H2 CH3 -CH=CH2 (propene) 3. From halogenated derivates Halogenated derivate + Zn ZnX2 + alkene (X=Cl,Br,I) ZnCl2 + CH2=CH2 (ethene)

Example: Cl-CH2-CH2 -Cl + Zn

4. From mono-halogenated derivates through dehydrogenating ( -HX) mono-halogenated derivate Examples: CH3 -CH2 -Cl CH2=CH2 + HCl (ethene) CH2=CH-CH2 -CH3 (1 butene) alkene + HX (X=Cl,Br,I)

Br-CH2-CH2-CH2-CH3

5. By dehydrating the alcohols (-H2O) alcohol Examples: CH3 -OH CH3 -CH2 -OH CH2=CH2 + H2 O (ethene) CH2=CH-CH3 + H2 O (1-butene) alkene + H2 O

Chemical reactions

1. Hydrogen addition (hydrogenating) alkene + H2 alkane

Examples: CH2=CH-CH3 + H2 CH3-CH2-CH3 (propane) CH3-CH=CH-CH3 + H2 CH3-CH2-CH2-CH3 (n butane) 2. X2 addition (halogenations) Cl 2, Br2, I2 alkene + X2 halogenated derivate vicinal Examples: CH2=CH-CH2-CH3 + Cl2 CH2Cl-CHCl-CH2-CH3 (1,2-dichlorbhutan) CH2=CH2 + Br2 CH2 Br-CH2 Br (1,2-dibromethan) 3. HX addition (HCl, HBr, HI) alkene + HX mono-halogenated derivate

Examples: CH2=CH2 + HBr CH3-CH2 -Br (ethyl bromide) CH3 -CH2=CH-CH3 + HCl CH3-CH2 -CHCl-CH3 (s butyl chloride) 4. H2O addition (hydration)

alken + H2O

alcohol

Examples: CH2=CH2 + H2O CH2=CH-CH3 + H2 O

CH3 -CH2-OH (ethylic alcohol) CH3-CHOH-CH3 (isopropyl alcohol)

5. HBr addition in the presence of peroxides R-CH=CH2 + HBr R-CH2-CH2-Br

6. Hipologenos acid addition (HOX) Examples: CH2=CH2 + HOCl CH2=CH-CH2-CH3

CH2-OH-CH2-Cl (2-clor, 1-hidroxoethane) CH2 -OH-CH-Br-CH3 (1-brom, 2-hidroxopropane)

7. Polymerization reaction CH2=CH2 grade (-CH2-CH2 -)(n) polyethene / polyethylene - polymer; n = polymerization

At the polymerization, the chains dont usually have the same size, hence, n is a medium value it is called the medium grade of polymerization. 8. Oxidation a) Complete (combustion): C nH2n + O2
nCO2

+ nH2O + Q ethane oxide (instable)

b) With O2 in the presence of Ag / 250 grades: alkene + 1/2 O2 +H2O diol

c) Mild oxidation - Bayer: KMnO4, H2O or Na2SO3: alkene + [O] + H2O

diol

Use
ethene and propene are the organic compounds in the biggest quantity on world-wide plan. Ethene occupies the fourth place in the production of all chemical compounds (it is overtaken only by sulphuric acid, nitrogen and oxygen). The most important chemical transformations of ethene, used at a large scale, are: polyethene, acetic acid, PVC. ethene is produced by plants and it stimulates the growth of fruits, the sprout of seeds and the ripe of flowers

Alkynes - Organic Chemistry Tutor


The acyclic hydrocarbons with one triple bound in the molecule are called alkynes. The still customary denomination of acetylene comes from the series first hydrocarbon, acetylene.

Structure
Acetylene has the composition C2 H2: it contains two carbon atoms connected through a triple bound: CH CH. The C-H bounds of acetylene are formed by the interpenetration of an orbital sp from the carbon atom with an orbital s from the hydrogen atom; the triple bound is made of one sigma bound (formed by the interpenetration of two orbital sps from each carbon atom) and two pi bounds (result of the interpenetration of two pairs of orbital ps). Same as for ethylene, for detaching the pi bounds a smaller quantity of energy is necessary unlike for detaching the sigma bounds. The isomers for compounds with triple bound are unknown, because all the atoms are positioned collinear. Acetylene derivates (obtained through the substitution of one or both hydrogen atoms with radical alkyls) can be considered the homologues of acetylene. Therefore, by substituting one hydrogen atom with one methyl radical you obtain propine C3 H4: CH C-CH3. Also, if one hydrogen atom of acetylene is substituted with a C2 H5 radical, you obtain ethyl acetylene, meaning 1-butine. The isomer of 1-butine is 2-butine, in other words the hydrocarbon containing the triple bound is between C2-C3. This compound can be taken as a deriving from acetylene by the replacement of the two hydrogen atoms with a CH3 radical, resulting a dimethylacetylene: CH3-CH2-CH2-C C-CH3 is 2-hexine. Sometimes more alkynes are denominated as acetylene substitution products; for example, dimethylacetylene as 2-butine. The derivate radicals of alkynes are called alkynyls, for example CH C-CH2 is called 2-propinyl.

General formula
Unsaturated hydrocarbons with a triple bound in the molecule, containing 2 atoms less than the corresponding saturated hydrocarbons, have the general formula CnH2n-2.

Physical properties
At usual temperature, the C2-C4 alkynes are gases, C4-C14 are liquids, and the superior ones are solids. Their boiling points are similar, yet a bit higher than the alknes and alkenes points. Their solubility is higher than their corresponding saturated hydrocarbons.

Chemical properties
The chemical behavior of the alkynes is characterized by their capacity of giving addition reactions, polymerization reactions and metallic derivates forming reactions. A great part of reactions are known as belonging to acetylene.

Obtaining methods

1. Methane pyrolize 2CH4 CH CH + 3H2 (acetylene)

2. Obtaining alkynes out of alkenes (X=Cl 2, Br2, I2) R-CH=CH-R' + X2 R-CHX-CHX-R' R-C C-R' + 2HX

3. Obtaining alkynes out of halogenated derivates R-X + NaC C-R' NaX + R-C C-R' (alkyne)

Chemical reactions

1. H2 addition (hydrogenating) R-C C-R' + H2 R-C C-R' + 2H2 R-CH=CH-R' (alkene) R-CH2 -CH2 -R' (alkane)

2. X2 addition (in action less solvent) CnH2n-2 + X2 nC + 2n-2HX (without a solvent, a explosion may take place) R-C C-R' + X2 R-CX=CX-R' (dihalogenated derivate) - using a action less solvent) Examples: CH CH + Cl2 CH CH + Cl2 tetraloretane) 3. HX addition R-C CH + HX Examples: CH CH + HCl CH C-CH3 + HCl R-CX=CH2 + HX R-CX2-CH3 (geminal dihalogenated derivate) 2C + 2HCl - explosion CHCl=CHCl (1,2 dichloretene) + Cl2

CHCl2-CHCl2 (1,1,2,2 -

CHCl=CH2 + HCl (vinyl chloride) + HX R-CX2-CH3 CH2=CCl-CH3 + HCl CH3-CCl2-CH3

4. H2O addition (hydration, catalyser: HgSO4 and H2SO4 ) R-C CH + H2 O R-COH=CH2 (instable enol) (tautomeryzation) R-C=O-CH3

5. Prussic acid addition (HCN - catalyser Cu2 Cl2, NH4Cl)

R-CH CH + HCN

R-CCN=CH2

6. CH3-COOH addition (catalyser: Zn(CH3 COO)2 / 200 grade) R-C CH + CH3 -COOH R-COOCH3=CH2 (acetate)

7. Poly addition reactions (polymerization) - dimerization, trimerization, tetramerization a) Dimerization reaction CH CH + CH CH CH C-CH=CH2 (acetylene vinyl) b) Trimerization reaction (it takes place in ceramic tubes at temperatures within 600-800 Celsius degrees) 3CH CH

8. Oxidation reaction a) Complete: C nH2n-2 + 3n-1/2 O2 b) Incomplete CH CH + 4[O] CH3-C CH + 3[O] nCO2 + n-1H2 O + Q

COOH-COOH (oxalic acid) CH3 -C=O-COOH (piruvic acid)

Use
acetylene was and still is one of the most used raw material of the of the organic chemistry industry from acetylene you can obtain rubber, vinyl poly chloride and many more.

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