Chapter 10Structure and Synthesis of Alcohols.ppt

Chapter 10 Chapter 10Structure and Synthesis of Alcohols Structure of Alcohols Hydroxyl (OH) functional group Oxygen is sp3 hybridized.  = Classification Primary: carbon with –OH is bonded to one other carbon. Secondary: carbon with –OH is bonded to two other carbons. Tertiary: carbon with –OH is bonded to three other carbons. Aromatic (phenol): -OH is bonded to a benzene ring. = Classify these: IUPAC Nomenclature Find the longest carbon chain containing the carbon with the -OH group. Drop the -e from the alkane name, add -ol. Number the chain, starting from the end closest to the -OH group. Number and name all substituents. = Name these: Unsaturated Alcohols Hydroxyl group takes precedence. Assign that carbon the lowest number. Use alkene or alkyne name. Naming Priority Acids Esters Aldehydes Ketones Alcohols Amines Alkenes Alkynes Alkanes Ethers Halides  = Hydroxy Substituent When -OH is part of a higher priority class of compound, it is named as hydroxy. Example: Common Names Alcohol can be named as alkyl alcohol. Useful only for small alkyl groups. Examples: Naming Diols Two numbers are needed to locate the two -OH groups. Use -diol as suffix instead of -ol. Glycols 1, 2 diols (vicinal diols) are called glycols. Common names for glycols use the name of the alkene from which they were made. Naming Phenols -OH group is assumed to be on carbon 1. For common names of disubstituted phenols, use ortho- for 1,2; meta- for 1,3; and para- for 1,4. Methyl phenols are cresols. Physical Properties Unusually high boiling points due to hydrogen bonding between molecules. Small alcohols are miscible in water, but solubility decreases as the size of the alkyl group increases.  = Boiling Points Solubility in Water Methanol “Wood alcoh