Functional Groups

Alkane (Substituent: alkyl)

* a hydrocarbon with no multiple bonds


* nonpolar
* tetrahedral (sp3 hybridized)
* free radical reactions

Alkene (Substituent: alkenyl)

* a hydrocarbon with at least 1 C-C double bond
* nonpolar
* trigonal planar (sp2 hybridized)
* addition reactions, oxidative cleavage
* stability increases with # carbons attached

Alkyne (Substituent: alkynyl)

* a hydrocarbon with at least 1 C-C triple bond
* nonpolar
* linear (sp hybridized)
* addition reactions, oxidative cleavage, acid-base reactions

Benzene Ring (Substituent: phenyl)

* a 6-membered ring containing 3 alternating double bonds
* substitution reactions (less reactive than normal alkenes bc aromaticity)

Alcohol (Substituent: hydroxy)

* OH group attached to C (unless attached to C=O)
* polar (OH does hydrogen bonding)
* acid-base reactions, substitution reactions, oxidation reactions

ether (Substituent: alkoxy)

* an oxygen flanked by two carbons
* borderline between polar and nonpolar (dipole-dipole)
* acid-base reactions

alkyl halide (Substituent: haloalkyl)

* an alkyl group attached to a halogen
* considered nonpolar but more polar than alkanes
* substitution and elimination reactions

amine (Substituent: amino)

* a nitrogen attached to a simple carbon or hydrogen atoms
* polar (N-H does hydrogen bonding)
* acid-base, substitution reactions

aldehyde (Substituent: oxo)

* a carbonyl (C=O) attached to hydrogen and another carbon
* C=O bond is somewhat polar
* addition reactions

ketone (Substituent: oxo)

* a carbonyl (C=O) flanked by two carbons
* C=O bond is somewhat polar
* addition, acid-base reactions

carboxylic acid (suffix: -oic acid)

* a carbonyl (C=O) adjacent to a hydroxyl (OH) and an R group
* acid-base, acyl substitution reactions

ester

* a carbonyl group adjacent to an alkoxy (OR) and an R group
* acyl substitution reactions and addition reactions

thiol (Substituent: mercapto)

* sulfur-containing analogs of alcohols
* acid-base reactions, substitution reactions

sulfide (suffix: sulfide)

* a sulfur flanked by two carbon atoms
* reduction reactions

epoxide (suffix: oxide)

* cyclic ethers consisting of a 3-membered ring containing 1 oxygen and two carbons
* ring opening when treated with nucleophiles

nitrile (suffix: nitrile)

* a molecule containing the CN group
* reduction reactions, hydrolysis reactions

imine (suffix: imine)

* nitrogen-containing analogues of ketones and aldehydes
* reduction reactions, hydrolysis

acyl halide (suffix: -oyl halide)

* Carboxylic acid derivatives where OH has been replaced by a halogen
* acyl substitution reactions

amide (suffix: amide)

* nitrogen-containing analogues of esters
* reduction reactions, hydrolysis reactions

anhydride (suffix: anhydride)

* oxygen atoms flanked by two acyl groups
* acyl substitution reactions, reduction reactions

Nitro

* a molecule containing the NO2 group
* reduction reactions, acid-base reactions

Enol

* alkenes attached to a hydroxyl substituent
* good nucleophiles, will perform addition reactions to aldehydes and ketones
* also will tautomerize to aldehydes and ketones

Enolate

* the conjugate bases of enols
* excellent nucleophiles
* addition reactions to aldehydes and ketones
* substitution reactions with alkyl halides

Enamine

* alkenes attached to an amino substituent
* excellent nucleophiles
* addition reactions to aldehydes and ketones
* substitution reactions with alkyl halides

tert-butyl

isopropyl

isobutyl

sec-butyl