Alkanes. ! An alkane is a hydrocarbon with only single bonds. ! Alkanes have the general formula: C n H 2n+2
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1 ALKANES Chapter 4
2 Alkanes! An alkane is a hydrocarbon with only single bonds.! Alkanes have the general formula: C n 2n+2! Alkanes can be straight-chain or branched.
3 Properties of isomers! Constitutional (structural) isomers have the same molecular formula but different connectivity of atoms.! Constitutional isomers have different physical properties.
4 Constitutional Isomers
5 IUPAC and Nomenclature
6 Naming straight-chain or unbranched alkanes Simple straightchain alkanes are named using a prefix relating to the number of carbons, followed by the suffix -ane.
7 Nomenclature of Unbranched Alkanes
8 Nomenclature of Unbranched Alkyl groups! The unbranched alkyl groups are obtained by removing one hydrogen from the alkane and named by replacing the -ane of the corresponding alkane with -yl
9 Nomenclature of Branched-Chain Alkanes (IUPAC) 1) Locate the longest continuous chain of carbons; this is the parent chain and determines the parent name.! When two chains of equal length compete to be parent, choose the chain with the greatest number of substituents. 2) Number the longest chain beginning with the end of the chain nearer the substituent so that the substituent gets the lowest number possible.! If two substituents are present, number from the end to give the lowest number possible to the first substituent.! If two substituents are the same number of carbons from either end, number the compound to give the second substituent the lowest number (or third substituent, etc.)
10 Nomenclature of Branched-Chain Alkanes (IUPAC) 3) Identify each substituent and note the location (number of carbon) it is attached to on the parent compound (longest C chain). 4) When two or more substituents are identical, indicate which carbons the substituents are attached to with a numeral, and use the prefixes di-, tri-, tetra- etc.! Commas are used to separate numbers from each other. 5) Substituents are listed alphabetically.! Ignore prefixes like di-, tri, tetra, etc.! Ignore hyphenated prefixes like tert- and sec-, etc.. 6) In writing the name of the compound, designate the location and name of each substituent, followed by the name of the parent compound.
11 Nomenclature of Branched Alkyl Chains! Two alkyl groups can be derived from propane.! Four groups can be derived from the butane isomers.! Another common group is the neopentyl group.
12 Cycloalkanes! The prefix cyclo- is added to the name of the alkane with the same number of carbons.! When one substituent is present it is assumed to be at position one and is not numbered.! When two alkyl substituents are present the one with alphabetical priority is given position 1.! Numbering continues to give the other substituent the lowest number.! ydroxyl has higher priority than alkyl and is given position 1.! If a long chain is attached to a ring with fewer carbons, the cycloalkane is considered the substituent.
13 Sigma Bonds & Rotation! Sigma bonds allow for rotation around the bond.! The molecule ethane, C 2 6, has relatively free rotation around its sigma bonds.! owever, as rotation occurs around the sigma bonds, the attached hydrogens change their relative positions in space.! These temporary shapes are called conformations.! Each possible shape is called a conformer.
14 Representing Confomers! A sawhorse formula gives a 3-dimensional view of ethane using a standard bond-line structure. Eclipsed Staggered
15 ! A Newman projection is another means of representing and analyzing confomers.! To draw a Newman projection, imagine looking at one of the carbons of the bond being examined head on.! The dihedral angle is the angle between two hydrogens on adjacent carbons, as viewed in a Newman projection. Newman Projections
16 Barrier to Rotation & Stability of Confomers
17 ! Build a model of butane. Butane! Draw all possible eclipsed and staggered conformations.! Consider the relative energies of the various confomers.
18 Butane
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