Functional Groups

Organic Chemistry Essentials

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Definitions

alkane alkene alkyne alcohol aldehyde ketone carboxylic acid ether ester amine

consists of only carbon to carbon single bonds consists of at least one carbon to carbon double bond consists of at least one carbon to carbon triple bond contains an -OH group contains a terminal O=C-H group contains an internal C=O group contains a terminal O=C-OH group contains an internal O-O group contains an internal O=C-O- group contains a terminal NH2 group

Alkane

Alkyl, and occasionally aryl (aromatic) functions are represented by the RMethyl: CH3 Ethyl: CH3CH2 Propyl: CH3CH2CH2 Isopropyl: (CH3)2CH Phenyl: C6H5 etc.

Alkyl halide

Alkyl halides [haloalkanes] consist of an alkyl group attached to a halogen: F, Cl, Br, I. Chloro, bromo and iodo alkyl halides are often susceptible to elimination and/or nucleophilic substitution reactions.

Primary alcohol

Primary alcohols have an -OH function attached to an R-CH2- group. Primary alcohols can be oxidised to aldehydes and on to carboxylic acids. (It can be difficult to stop the oxidation at the aldehyde stage.) Primary alcohols can be shown in text as: RCH2OH

Secondary alcohol

Secondary alcohols have an -OH function attached to a R2CH- group. Secondary alcohols can be oxidised to ketones.

Secondary alcohols can be shown in text as: R2CHOH

Tertiary alcohol

Tertiary alcohols have an -OH function attached to a R3C- group. Tertiary alcohols are resistant to oxidation with acidified potassium dichromate(VI), K. Tertiary alcohols can be shown in text as: R3COH

Aldehyde

Aldehydes have a hydrogen and an alkyl (or aromatic) group attached to a carbonyl function. Aldehydes can be shown in text as: RCHO Aldehydes are easily oxidised to carboxylic acids, and they can be reduced to primary alcohols. Aldehydes can be distinguished from ketones by givin positive test results with Fehlings solution (brick red precipitate) or Tollens reagent (silver mirror). Aldehydes give red-orange precipitates with 2,4dinitrophenyl hydrazine.

Ketone

Ketones have a pair of alkyl or aromatic groups attached to a carbonyl function. Ketones can be shown in text as: RCOR Ketones can be distinguished from aldehydes by givin negative test results with Fehlings solution (brick red precipitate) or Tollens reagent (silver mirror). Ketones give red-orange precipitates with 2,4-

dinitrophenyl hydrazine.

Carboxylic acid

Carboxylic acids have an alkyl or aromatic groups attached to a hydroxy-carbonyl function. Carboxylic acids can be shown in text as: RCOOH Carboxylic acids are weak Bronsted acids and they liberate CO2 from carbonates and hydrogen carbonates.

Carbonyl function

The carbonyl group is a super function because many common functional groups are based on a carbonyl, including: aldehydes, ketones, carboxylic acids, esters, amides, acyl (acid) chlorides, acid anhydrides

Ester

Esters have a pair of alkyl or aromatic groups attached to a carbonyl + linking oxygen function. Esters can be shown in text as: RCOOR or (occasionally) ROCOR. carboxylic acid + alcohol -> ester + water This is an acid catalysed equilibrium.

Amide

Primary amides (shown) have an alkyl or aromatic group attached to an amino-carbonyl function. Primary amides can be shown in text as: RCONH2 Secondary amides have an alkyl or aryl group attache to the nitrogen: RCONHR Tertiary amides have two alkyl or aryl group attached to the nitrogen: RCONR2

Primary amine

Primary amines have an alkyl or aromatic group and two hydrogens attached to a nitrogen atom. Primary amines can be shown in text as: RNH2 Primary amines are basic functions that can be protonated to the corresponding ammonium ion. Primary amines are also nucleophilic.

Secondary amine

Secondary amines have a pair of alkyl or aromatic groups, and a hydrogen, attached to a nitrogen atom. Secondary amines can be shown in text as: R2NH Secondary amines are basic functions that can be protonated to the corresponding ammonium ion. Secondary amines are also nucleophilic.

Tertiary amine

Tertiary amines have three alkyl or aromatic groups attached to a nitrogen atom. Tertiary amines can be shown in text as: R3N Tertiary amines are basic functions that can be protonated to the corresponding ammonium ion. Tertiary amines are also nucleophilic.