Organic Chemistry

• Longest carbon chain containing the highest-order functional group

  Parent chain
• Numbering the carbon chain

  Carbon numbered 1 is closest to the highest-priority functional group
• Substituents


  Functional groups that are not part of the parent chain
• IUPAC Naming


  1. Identify the longest carbon chain containing the highest-order functional group

  2. Number the chain

  3. Name the substituents

  4. Assign a number to each substituent

  5. Complete the name
• No two distinct compounds have the same IUPAC name
• Hydrocarbons


  • Contain only carbon and hydrogen atoms
• Alkanes


  Simple hydrocarbon molecules with the formula CnH(2n+2)
• Alkyl halides


  Alkanes with halogens as substituents, indicated by prefixes like fluoro-, chloro-, bromo-, or iodo-
• Alkynes


  Hydrocarbons with triple bonds, indicated by the suffix -yne
• Diols


  Alcohols with two hydroxyl groups, indicated with the suffix -diol
• Geminal diols


  Diols with hydroxyl groups on the same carbon
• Vicinal diols

  Diols with hydroxyl groups on adjacent carbons
• Geminal diols spontaneously dehydrate to produce carbonyl compounds
• Alkane naming


  Named according to the number of carbons present followed by the suffix -ane
• First four alkanes


  • Methane (CH4)
  • Ethane (C2H6)
  • Propane (C3H8)
  • Butane (C4H10)
• Larger alkanes


  Use the Greek root for the number (pentane, hexane, heptane, octane, and so on)
• Alkenes


  Contain double bonds, named by substituting -ene for the suffix and numbering the double bond by its lower-numbered carbon
• Alkynes


  Contain triple bonds, substitute -yne with the same numbering
• Alcohols


  Contain a hydroxyl (-OH) group, which substitutes for one or more of the hydrogens in hydrocarbons

  
• Assigning numbers to substituents

  Determine the carbon to which it is bonded
• Completing the name


  1. Alphabetize the substituents

  2. Separate numbers from each other by commas

  3. Separate numbers from words by hyphens
• Naming alkanes


  1. According to the number of carbons present

  2. Followed by the suffix -ane
• Naming larger alkanes


  Use the Greek root for the number (pentane, hexane, heptane, octane, etc.)
• Alkenes


  Contain double bonds
• Alkynes


  Contain triple bonds
• Naming alkenes


  1. Substitute -ene for the suffix

  2. Number the double bond by its lower-numbered carbon
• Naming alkynes


  Substitute -yne with the same numbering
• Alcohols


  Contain a hydroxyl (-OH) group

  
• Naming alcohols

  1. Substitute the suffix -ol

  2. Use the prefix hydroxy- if a higher-priority group is present
• Alcohols have higher priority than double or triple bonds and alkanes
• Common names of alcohols


  Name of the carbon chain followed by the word alcohol (e.g. ethyl alcohol = ethanol)

  
• Diols


  • Contain two hydroxyl groups
  • Geminal if on the same carbon
  • Vicinal if on adjacent carbons
• Aldehydes


  Contain a carbonyl group on a terminal carbon also attached to a hydrogen atom
• Naming aldehydes


  1. Use the suffix -al

  2. Use the prefix oxo- if a higher-priority group is present
• Common names of aldehydes

  • Formaldehyde for methanal
  • Acetaldehyde for ethanal
  • Propionaldehyde for propanal
• Ketones


  Contain a carbonyl group on a nonterminal carbon

  
• Naming ketones


  1. Use the suffix -one

  2. Use the prefix oxo- if a higher-priority group is present

  3. Can also use the prefix keto-
• Common names of ketones

  Name the alkyl groups on either side alphabetically and add "ketone" (e.g. 2-butanone = ethylmethylketone)

  
• Acetone


  The smallest ketone, IUPAC name is propanone
• Carbonyl-containing compounds


  Carbons adjacent to the carbonyl are the α-carbons