7. Naming (& Drawing) Hydrocarbon Derivatives Part 2

• Top 5 hydrocarbon derivatives in terms of functional group priority

  • carboxylic acids
  • esters
  • amides
  • aldehydes
  • ketones
• Alcohols

  Hydrocarbons that contain a hydroxyl group (oxygen single bonded to a hydrogen)
• Alcohols

  • Alcohols are named by adding the suffix -ol to the name of the parent chain
  • If there is more than one possibility for the location of the hydroxyl group (-OH), the location is indicated by a number in front of the -ol
• Polyalcohols

  Contain more than one hydroxyl group (-OH)
• Polyalcohols

  • pentane-1,3,5-triol
• Alcohols

  • If there are side groups on the main chain, they are named and numbered in the same way as for hydrocarbons
  • The parent chain must contain the hydroxyl groups
• Alcohols

  • 4-ethylheptane-2,3-diol
• Alcohols

  • If a higher priority functional group is present, the hydroxyl groups may be named and numbered as the side group hydroxy-
• Alcohols

  • 3-hydroxypentanoic acid
• Alcohols

  • 2,3-dimethylbutan-2-ol
  • cyclooctane-1,2,5-triol
• Amines

  Contain a nitrogen that is attached to a hydrocarbon chain
• Amines

  • The longest hydrocarbon chain bonded to the nitrogen atom is considered the parent chain
  • The ending of the parent alkane is changed to -amine
  • If the parent chain has 3 or more carbons, the location of the nitrogen atom is added in front of the -amine
• Amines

  • pentan-2-amine
• Amines

  • For secondary and tertiary amines, the smaller hydrocarbon chains bonded to the N are named as alkyl groups
  • Instead of a number, N- is added to the alkyl group names to indicate that they are attached to the nitrogen
  • If there are two of the same group, N,N-di- is added to the alkyl group name
• Amines

  • N-isopropyl-N-methylbutan-1-amine
• Amines

  • If there are side groups on the parent chain, they are named and numbered in the same way as for other organic compounds
• Amines

  • N-t-butyl-6-cyclopropyl-5-methyl-N-propylheptan-3-amine
• Amines

  • If a higher priority functional group is present, the -NH2 group can be named as an amino side group
• Amines

  • 5-aminoheptanal
• Amines

  • N-ethyl-2-methylpentan-3-amine
• Ethers

  Organic compounds that contain an oxygen atom bonded between 2 alkyl groups
• Ethers

  • Ethers are not named by changing the suffix of the parent chain
  • The longest carbon chain that is bonded to the oxygen atom determines the root and suffix
  • The shorter alkyl group that is bonded to the oxygen atom is treated as a side group, called an alkoxy group
• Ethers

  • 1-ethoxypropane
  • 2-methyl-4-propoxyhexane
• Ethers

  • 3-isopropoxy-2-methylpent-1-ene
• Functional group priorities

  • Carboxylic acids
  • Esters
  • Amides
  • Aldehydes
  • Ketones
  • Benzene
  • Alkene
  • Alkyne
  • Alkane
  • Haloalkanes
• Haloalkanes

  Hydrocarbons that contain at least one halogen atom
• Haloalkanes

  • Haloalkanes are named in the same way as alkanes
  • The halogens are named and numbered as side groups
• Haloalkanes

  • 6-bromo-2,2-dichloro-4-ethylheptane
  • 1-fluoro-3,4-diiodocyclopentane
• Putting it all together

  • 2-amino-3,4,5,6-tetrahydroxyhexanal
  • 1-amino-3-chlorohex-4-ene-2-ol
  • N-butyl-7-ethoxy-2-isopropyl-N-methyl-4-phenyloctanamide