Structure and Synthesis of Alcohols. Structure of Alcohols Hydroxyl (OH) functional group Oxygen is sp 3 hybridized. =>

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Presentation transcript:

Structure and Synthesis of Alcohols

Structure of Alcohols Hydroxyl (OH) functional group Oxygen is sp 3 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: 2-methyl-1-propanol 2-methyl-2-propanol 2-butanol 3-bromo-3-methylcyclohexanol =>

Unsaturated Alcohols Hydroxyl group takes precedence. Assign that carbon the lowest number. Use alkene or alkyne name. 4-penten-2-ol (old) pent-4-ene-2-ol (1997 revision of IUPAC rules) =>

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: 4-hydroxybutanoic acid also known as GHB =>

Common Names Alcohol can be named as alkyl alcohol. Useful only for small alkyl groups. Examples: isobutyl alcohol sec-butyl alcohol =>

Naming Diols Two numbers are needed to locate the two -OH groups. Use -diol as suffix instead of -ol. 1,6-hexanediol =>

Glycols 1, 2 diols (vicinal diols) are called glycols. Common names for glycols use the name of the alkene from which they were made. 1,2-ethanediol ethylene glycol 1,2-propanediol propylene glycol =>

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. 3-chlorophenol meta-chlorophenol 4-methylphenol para-cresol =>

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. =>