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Importance of carbon
Basis for all life. Form stable covalent bonds to other carbon atoms - catenation. Can form single, double and triple bonds. Long carbon chains can be produced. Will bond with many other elements. A HUGE number of chemicals are possible.
Organic Compounds Alkanes
Allotropic forms of carbon
Elemental carbon exists in 4 forms. Amorphous- no deﬁnite structure Graphite- layered sheets of rings Diamond- tetrahedral Spherical- combination of rings
Classes of organic compounds
We commonly look at organic species by class. Alkanes simplest class of organic compounds contain only carbon and hydrogen only have single bonds
H H H C H H
Molecular Formula C5H12
Possible line representations
CH3CH2CH2CH2CH3 n-pentane CH3CH(CH3)CH2CH3 2-methylbutane
H H H H C C
H H H H C C H H
H H H H C C
H C H H
H C H H H
All are structural isomers of C5H12. This system is used to show the arrangement of atoms in a molecule in a single line.
. H H C H H C H H CH3CH(CH3)CH2CH3 CH3 H3C CH C H2 CH3 Example. giving us 4 equivalent orbitals. • single bond = bond order of 1 • double bond = bond order of 2 = bond order of 3 • triple bond Models are useful to help see these shapes. Example Propane CH3CH2CH3 Shapes of organic molecules Properties of organic compounds are related to their geometry. • Bonds are represented as lines. Propane H C H (CH3)4C CH3 H3C C CH3 CH3 Condensed formula • A type of line format. • The s and p orbitals are very close in energy so the four electrons spend time in the s and the 3 different p.Structural isomers Compounds with the same number of atoms and bonds but with different arrangements. . how do we get a tetrahedral shape? ” • The reason is that the s and p orbitals will blend together. • Lists all atoms in order and tells how they are bound together. . • Shorthand way of writing formula. Bond order will help to determine geometry. Models Three dimensional representations Ball and stick Space ﬁlling Ethane • Bond order = 1 • Single C-C bond • Tetrahedral geometry Hybridization You should be asking . CH3CH2CH2CH2CH3 H3C H2 C C H2 H2 C CH3 Formula Structural Formula • Shows all atoms with bonds. . • This process is called hybridization. “ If carbon has two s electrons and two p electrons.
sp hybrid • Linear geometry Classifying organic compounds Classify compounds by functional group. • contain only hydrogen and carbon • only have single bonds All members have the general formula of CnH2n+2 First four members of the alkanes Name Methane Ethane Propane Butane # of C 1 2 3 4 Condensed formula CH4 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 Alkanes R.sp2 hybrid • Planer geometry Bond length and strength bond length distance between two bonded atoms. Called a homologous series “Only differ by number of CH2 groups” . all of the orbitals are hybrids. Functional group Speciﬁc combination of atoms that gives a known type of behavior Hydrocarbons Alcohols Acids Amines Ketones Aldehydes C and H only R-OH R-COOH R-NH2 R(C=O)R’ C=O R-CHO Simplest members of the hydrocarbon family. sp3 25% s and 75% p character We’ll look at other hybrids in the next chapter. single bonds > double bonds > triple bonds bond strength energy necessary to break a chemical bond. R’ = any hydrocarbon chain. triple bonds > double bonds > single bonds Ethyne • Bond order = 3 • Triple C-C bond .Hybridization 1 s +3 Ethane sp3 hybrids 1s orbital of H 4 p sp3 C ! bond C In the case of a carbon that has 4 single bonds. Ethene • Bond order = 2 • Double C-C bond .
56. Go ﬁgure? Prop But Pent Hex Hept Oct Non Dec .0 -187. Find the longest carbon chain..546 0.730 These go up These go up as the number as the number of carbons of carbons increase. don’t count.7 .424 0.. Use base names with a yl ending.8 -53.5 . Base names Preﬁx Meth Eth Length of carbon chain 1 2 3 4 5 6 7 8 9 10 Naming alkanes C-C-C-C-C-C Six carbon atoms in the longest chain use base name of hex All carbon and hydrogen with single bonds use ane ending Name of compound is hexane Preﬁxes are derived from Greek (except for ‘Non’ which is from Latin. tri. Organic nomenclature Organic molecules can be very complex.7 . 5.2 -0.718 0.42.90. modify name with di. 2.684 0.94.0 -129.Alkanes Physical Properties Non-polar molecules Not soluble in water Low density Low melting point Low boiling point Alkanes Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane BP (oC) -161. Locate any branches on chain. . Naming system must be able to tell Naming alkanes 1.626 0. Number the location of each branch.5 36.7 -29.7 174.. .88.579 0.6 -172.. tri.4 125.703 0. 4.1 -135.659 0.1 68.6 . Use as base name with an ane ending.6 150. • Number of carbons in the longest chain • The location of any branches • Where functional groups are (if any) The IUPAC Nomenclature System provides a uniform set of rules that we can follow. List multiple branches alphabetically the di. For multiple branch of the same type. increase.7 98.0 .582 0. 3.0 MP (oC) -182..7 Density 0.
use but All C and H with single bonds .CH3 H3C CH C H2 CH3 Examples C-C-C-C-C-C | | 3. Use 2.3.2-dimethylhexane 4-propylheptane .8-pentamethyldecane C Another example Name the following.it may help.on 2nd carbon .7.use ane Parent name: butane CH3. C C | | C-C-C-C-C-C Now name it! Another example C C | | C-C-C-C-C-C 1.methyl 2-methylbutane 3-ethyl-5-methylheptane C-C-C-C-C-C-C | | C-C C C-C-C-C C-C-C | | C-C-C-C-C-C-C | 2.hexane 2. First convert it to a carbon skeleton.3.5-dimethyl heptane C-C C Longest C chain has 4 carbon .dimethyl 3. leaving out the hydrogens . Two methyl groups .5-dimethylhexane Even more examples 3-ethyl-2. Longest chain is 6 . Another example (CH3)2CHCH2CH2CH(CH3)2 (CH3)2CHCH2CH2CH(CH3)2 This is a condensed structural formula.
dry cleaning ﬂuid • This is a substitution reaction .4-dimethylcyclohexane CH3 1-cyclohexylheptane H2C H3C C H C H2 H2 C CH cis-1.2-dichloroethane . Reactions of alkanes Halogenation A reaction where a halogen replaces one or more hydrogens. C-C • 2. We’ll worry about it in the next chapter. Cyclohexane as a branch would be cyclohexyl.natural gas Propane . ethylcyclopentane cis and trans isomers • The book discusses cis and trans isomers.4. CnH2n.mixture of hydrocarbons Used to prepare many solvents • dichloromethane . Named as the parent alkane but add cyclo• C-C C-C / \ C \ C / cyclohexane When they occur as a branch.Even more examples Cycloalkanes Cyclic alkanes of the general formula.used in gas grills Butane . use the same rules as with any branch.4. CH4(g) + Cl2(g) CH3Cl(g) + HCl(g) Reactions of alkanes Combustion CH4(g) + 2 O2(g) CO2(g) + 2H2O(g) Many alkanes are used this way . CH3 H2C HC C H2 H2 C CH CH2 cycloheptane CH3 cyclohexane trans-1.as fuels Methane .4-dimethylcyclohexane CH2 Sources of alkanes Alkanes can be obtained by refinement or hydrogenation of: petroleum shale oil coal Low molecular weight alkanes can be obtained directly from natural gas. CnH2n.used as anesthesia • chloroform 1.paint stripper .2. Named as the parent alkane but add cyclocyclo- 4-methyldecane C-C \ / C C-C | | cyclopropane cyclobutane Cyclic alkanes of the general formula.lighters Gasoline .6-pentamethylheptane Cycloalkanes. Just a couple of examples for now.
!Give the name and carbon number for the halide just like a side branch. !Follow the same system as with alkanes. • Increase with MW and number of halides. I Any alkane chain Structure and naming are similar to the alkanes. General formula Naming alkyl halides The names used for halogens are Halogen ﬂuorine chlorine bromine iodine Name ﬂuoro chloro bromo iodo Symbol -F -Cl -Br -I R-X A halogen F. 1-bromo-3-chloropropane Solubility • Not soluble in water. • Soluble in nonpolar solvents like alkanes other alkyl halides. (chloromethyl)cyclopropane . 1-fluoro fluoroethane Naming alkyl halides Nomenclature examples CH3CHBrCH3 2-bromopropane CH3CH2C(CH3)ClCH2CH2CH3 3-chloro-3-methylhexane CCl2F2 dichlorodiﬂuoromethane CH3C(CH3)ICH3 2-iodo-2-methylpropane 1-bromo bromo-2-methylpentane C-C-F C-C-C | C-C-C-C-C | 2-chloro chloropropane Cl C-Br Examples bromochloromethane Properties of alkyl halides Melting points and Boiling points • Higher than alkanes. Br. Cl.Alkyl halides Theses are alkanes with one or more halogens in place of hydrogen.
.tertiary . Reactions of alkyl halides .quaternary This is true for other functional groups as well Classiﬁcation of alkyl halides R-C-X Primary R | Tertiary R-C-R | X R-C-R Secondary | X R Quaternary | R-C-R | R Principal reaction type is halide exchange.a type of substitution reaction halide exchange CH3-Br + ICH3-Br + OHCH3-I + BrCH3-OH + Br- Note! Does not work with tertiary alkyl halides.secondary .Classiﬁcation of alkyl halides Based on the number of alkyl groups attached to the carbon. Results in four classes .primary .
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