Chapter 3Structure and Stereochemistryof Alkanes.ppt

Chapter 3 Chapter 3Structure and Stereochemistryof Alkanes Lower Membered Alkanestrivial (common) names METHANE BUTANES Pentanes Writing Isomers -Heptanes Common Names Isobutane, “isomer of butane” Isopentane, isohexane, etc., methyl branch on next-to-last carbon in chain. Neopentane, most highly branched Five possible isomers of hexane,18 isomers of octane and 75 for decane!  = IUPAC Names Find the longest continuous carbon chain. Number the carbons, starting closest to the first branch. Name the groups attached to the chain, using the carbon number as the locator. Alphabetize substituents. Use di-, tri-, etc., for multiples of same substituent. = Longest Chain The number of carbons in the longest chain determines the base name: ethane, hexane. (Listed in Table 3.2, page 81.) If there are two possible chains with the same number of carbons, use the chain with the most substituents. Number the Carbons Start at the end closest to the first attached group. If two substituents are equidistant, look for the next closest group. Name Alkyl Groups CH3-, methyl CH3CH2-, ethyl CH3CH2CH2-, n-propyl CH3CH2CH2CH2-, n-butyl Propyl Groups Butyl Groups Isobutyl Groups Alphabetize Alphabetize substituents by name. Ignore di-, tri-, etc. for alphabetizing. Complex Substituents If the branch has a branch, number the carbons from the point of attachment. Name the branch off the branch using a locator number. Parentheses are used around the complex branch name. Physical Properties Solubility: hydrophobic Density: less than 1 g/mL Boiling points increase with increasing carbons (little less for branched chains). Boiling Points of Alkanes Melting Points of Alkanes Branched Alkanes Lower b.p. with increased branching Higher m.p. with increased branching Examples: Major Uses of Alkanes C1-C2: gases (natural gas) C3-C4: liquified petroleum (LPG) C5-C8: gasoline C9-C16: diesel,