Organic Functional Groups and Nomenclature

1
Organic Functional Groups and Nomenclature

• CHEM 223
• Fall 2008

2
Hydrocarbon Nomenclature

• Find the longest continuous chain of carbons
• Count the number of carbons and assign a parent
  name
• Find the substituent groups and assign names
  (-yl) and numerical positions
• Assemble the name with correct punctuation and
  spelling

3
Basic IUPAC Nomenclature Rules

• Number of carbons in continuous chain or ring
  parent chain
• Identify functional group(s)
• Identify pendant groups
• Number the chain or ring
• Name the compound following basic rules of syntax
  (3-bromo-2-methylpentane)
• http//faculty.maryvillecollege.edu/bunde/nomencla
  ture.html

4
Nomenclature of Alkenes

• Follow the same rules for alkanes and find the
  longest continuous chain containing the double
  bond.
• Number the chain so that the double bond is found
  at the smallest numbered carbons
• Locate and name the substituent groups
• Assemble the name with the ene suffix

5
Cycloalkane Nomenclature

• Count the number of carbons in the ring and
  number around the ring so that the pendant groups
  are at the smallest number positions
• If the ring contains a double bond, the ring is
  numbered so that the double bond is in the
  C-1-C-2 position.
• Assign the names and positions of all pendant
  groups
• Assemble the name

6
Examples
7
Organic Functional Groups

• R-OH alcohols
• R-O-R ethers
• R-SH thioalcohols
• R-CHO aldehydes
• R-CO-R ketones
• R-COOH acids
• R-CC-R alkenes
• R-CO-O-R esters

• R-X alkyl halides
• R-CO-NHR amides
• R-NH2 amines
• Alkynes
• Cycloalkanes
• Aromatic Hydrocarbons

8
Organic Functional Groups
9
Nomenclature of Functional Groups

• Alkenes change parent chain to add ene
• Alkynes change parent chain to add yne
• Aromatic hydrocarbons derivatives of benzene and
  polyaromatic and heteroatomic aromatic compounds
• ortho, meta, para 1,2, 1,3, 1,4 disubstituted
• Common names of aromatic derivatives of benzene

10
Examples of Hydrocarbons
Geometric Isomers
11
Other Heteroatom Functional Group Nomenclature

• Alcohols change the parent alkane name by adding
  ol (alkyl alcohol contraction)
• Ethers name the two groups on either side of the
  O-
• Aldehydes change the parent name by adding al
  (for alkyl aldehyde)
• Ketones change the parent name by adding one
  (for alkyl ketone)

12
Capsaicin - Peppers