Chemistry Labs

Organic chemistry

IUPAC nomenclature, functional groups

Recognize common functional groups and build systematic names by choosing a parent chain, numbering it, and applying prefixes and suffixes.

IntuitionIntuition: a molecule’s name is a map

A systematic name encodes a structure: the parent tells the main carbon framework, locants show where features occur, and endings identify the highest-priority functional group. Learn to read the map in either direction.

Use the displayed structure to identify its characteristic group and connect it to the naming pattern.

SchoolSchool level: naming the parent

Definition:

Choose the longest chain containing the principal characteristic group (and as many multiple bonds as possible). Number it to give the principal suffix the lowest locant; then consider multiple bonds and substituents according to the applicable IUPAC rules.

Common groups and naming forms
ClassCharacteristic groupTypical name form
Alcoholhydroxy, –OHalkan-ol
Aldehyde–CHOalkan-al
Ketone>C=Oalkan-one
Carboxylic acid–COOHalkanoic acid

Example

Solution

The longest chain containing –OH has three carbons, so the parent is propane. Number from the nearer end: –OH is at C-2. The name is propan-2-ol.

UndergraduateUniversity level: priority and construction

When several characteristic groups occur, one is selected as the principal group and expressed as a suffix; other groups are usually named as prefixes. Functional-group seniority is not the same as the order in which groups are encountered while reading a formula. Apply the current IUPAC Blue Book rules for parent selection and tie-breaking.

Definition:

For an unsaturated alcohol, preserve the positions of both the double bond and –OH in the name: for example, but-3-en-2-ol has a four-carbon chain, a double bond beginning at C-3, and an –OH group on C-2. Modern placement of the terminal “e” follows the suffix-joining rules.

Example

Solution

The carboxyl carbon is part of the parent and is C-1. The four-carbon parent is butanoic acid; chlorine is on C-3. The name is 3-chlorobutanoic acid.

AdvancedAdvanced perspective: names as algorithms

Systematic naming can be viewed as a constrained optimization: identify admissible parent structures, rank them using ordered criteria, assign locants, then serialize the selected structure using prescribed nomenclature grammar. A name should map to one unambiguous molecular graph; retained and preferred IUPAC names remain useful exceptions in real chemical communication.

References

  • Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 · Henri A. Favre and Warren H. Powell, eds., 2014
  • Organic Chemistry · Jonathan Clayden, Nick Greeves, and Stuart Warren, 2012