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3.3 Alkyl Groups

🥼Organic Chemistry
Unit 3 Review

3.3 Alkyl Groups

Written by the Fiveable Content Team • Last updated September 2025
Written by the Fiveable Content Team • Last updated September 2025
🥼Organic Chemistry
Unit & Topic Study Guides

Alkyl groups are key players in organic chemistry, serving as building blocks for larger molecules. From simple methyl to complex neopentyl, these carbon-hydrogen structures vary in size and shape, influencing a compound's properties and reactivity.

Understanding alkyl groups is crucial for naming organic compounds and predicting their behavior. Whether straight-chain, branched, or cyclic, these groups form the backbone of many important molecules in chemistry and biology.

Alkyl Groups

Types of carbon atoms

  • Primary ($1°$) carbon atom bonded to one other carbon atom (methyl group, $CH_3-$)
  • Secondary ($2°$) carbon atom connected to two other carbon atoms (isopropyl group, $(CH_3)_2CH-$)
  • Tertiary ($3°$) carbon atom linked to three other carbon atoms (tert-butyl group, $(CH_3)_3C-$)
  • Quaternary ($4°$) carbon atom attached to four other carbon atoms (neopentyl group, $(CH_3)_3CCH_2-$)

Structures of alkyl groups

  • Methyl group ($CH_3-$) simplest alkyl group
  • Ethyl group ($CH_3CH_2-$) two carbon atoms in a straight chain
  • Propyl group ($CH_3CH_2CH_2-$) three carbon atoms in a straight chain
    • Isopropyl group ($(CH_3)_2CH-$) branched propyl with two methyl groups on the first carbon
  • Butyl group ($CH_3CH_2CH_2CH_2-$) four carbon atoms in a straight chain
    • sec-Butyl group ($CH_3CH_2CH(CH_3)-$) methyl group on the second carbon of a propyl chain
    • Isobutyl group ($(CH_3)_2CHCH_2-$) two methyl groups on the first carbon of a propyl chain
    • tert-Butyl group ($(CH_3)_3C-$) three methyl groups attached to a central carbon atom
  • Pentyl group ($CH_3CH_2CH_2CH_2CH_2-$) five carbon atoms in a straight chain
    • Isopentyl group ($(CH_3)_2CHCH_2CH_2-$) two methyl groups on the second carbon of a butyl chain
    • Neopentyl group ($(CH_3)_3CCH_2-$) three methyl groups attached to the first carbon of an ethyl chain
  • Cycloalkyl groups contain carbon atoms arranged in a ring structure
    • Cyclopropyl group ($c-C_3H_5-$) three-membered carbon ring
    • Cyclobutyl group ($c-C_4H_7-$) four-membered carbon ring
    • Cyclopentyl group ($c-C_5H_9-$) five-membered carbon ring
    • Cyclohexyl group ($c-C_6H_{11}-$) six-membered carbon ring

Applications of alkyl groups

  • Substituents are alkyl groups attached to a parent chain or ring named alphabetically before the parent (3-ethyl-2-methylpentane)
  • Longest carbon chain determines the base name of the compound numbered to give substituents lowest possible numbers (4-isopropyloctane vs. 6-methylnonane)
  • Branched alkanes named by identifying longest carbon chain with alkyl group substituents named and numbered based on position (3,4-dimethylhexane)
  • Cycloalkanes are saturated hydrocarbons containing a ring of carbon atoms named by prefixing "cyclo-" to corresponding alkane name (methylcyclohexane)
  • Bicyclic and polycyclic alkanes contain two or more fused rings numbered based on longest possible path through the rings (decahydronaphthalene or bicyclo[4.4.0]decane)

Nomenclature and Classification

  • Alkanes are hydrocarbons containing only single bonds between carbon atoms
  • IUPAC (International Union of Pure and Applied Chemistry) system provides standardized rules for naming organic compounds
  • Nomenclature involves systematically naming compounds based on their structure and functional groups
  • Hydrocarbons are compounds composed only of carbon and hydrogen atoms