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Chemistry · Ch 8 — Aldehydes, Ketones and Carboxylic Acids

Nomenclature

8.1.1

Nomenclature

Aldehydes and ketones are the simplest and most important carbonyl compounds, and each one can be named in two ways: an older common name and a systematic IUPAC name.

(a) Common names

Aldehydes. The common name of most aldehydes is built from the common name of the corresponding carboxylic acid, by dropping the acid's -ic ending and adding aldehyde in its place. Along with borrowing the acid's name, the common name also inherits the acid's Latin or Greek root (the original natural source of the acid or aldehyde) — which is why, for instance, the aldehyde derived from formic acid is formaldehyde, and the one derived from acetic acid is acetaldehyde (CH3CHO\text{CH}_3\text{CHO}).

Substituent positions in a common name are not given numbers — they are given Greek letters: α,β,γ,δ,…\alpha, \beta, \gamma, \delta, \dots starting right next to the carbonyl carbon. The α\alpha-carbon is the one directly bonded to the −CHO-\text{CHO} carbon, the β\beta-carbon is the next one along the chain, and so on. For example, a bromine on the third carbon of a four-carbon aldehyde chain is described as the β\beta-substituent, giving the name β\beta-bromobutyraldehyde.

Common-name examples of aldehydes as printed in the textbook: acetaldehyde written as CH3CHO, benzaldehyde drawn as a benzene ring bearing a CHO group, and beta-bromobutyraldehyde drawn as the chain H3C-CH-CH2-CHO with bromine bonded above the beta-carbon and the Greek position letters gamma, beta and alpha printed under the chain carbons.
Common-name examples of aldehydes as printed in the textbook: acetaldehyde written as CH3CHO, benzaldehyde drawn as a benzene ring bearing a CHO group, and beta-bromobutyraldehyde drawn as the chain H3C-CH-CH2-CHO with bromine bonded above the beta-carbon and the Greek position letters gamma, beta and alpha printed under the chain carbons.

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your textbook's own diagram.

Redrawn from the NCERT page with the structures, printed labels (CHO) and reagent placement exactly as the textbook prints them. Every element of this display was checked against the printed page during the sweep's blind-judge verification pass, so what …

Ketones. The common name of a ketone is built by naming the two alkyl or aryl groups attached to the carbonyl carbon (in alphabetical order), followed by the word ketone. Substituent positions are again marked with Greek letters, but here there are two chains radiating from the carbonyl carbon, so the labelling starts as α,α′\alpha, \alpha' on the two carbons flanking the carbonyl, then β,β′\beta, \beta', and so on outward.

Some ketones simply carry a historical common name instead — the simplest ketone, dimethyl ketone, is universally called acetone. Ketones in which one group is an aryl group and the carbonyl is attached directly to a benzene ring are commonly named by prefixing the name of the acyl group to the word -phenone: an acetyl group on a phenone gives acetophenone, a propionyl group gives propiophenone, and a benzoyl group (a second phenyl ring) gives benzophenone.

Common-name examples of ketones as printed in the textbook: acetone written as CH3-C-CH3 with the C=O drawn above the central carbon, and the three phenyl ketones acetophenone, propiophenone and benzophenone, each drawn with a Kekulé benzene ring bonded to the carbonyl carbon.
Common-name examples of ketones as printed in the textbook: acetone written as CH3-C-CH3 with the C=O drawn above the central carbon, and the three phenyl ketones acetophenone, propiophenone and benzophenone, each drawn with a Kekulé benzene ring bonded to the carbonyl carbon.

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your textbook's own diagram.

Redrawn from the NCERT page with the structures, printed labels (C, CH3, CH2, O) and reagent placement exactly as the textbook prints them. Every element of this display was checked against the printed page during the sweep's blind-judge verification pass, so wha …

(b) IUPAC names

The IUPAC name of an open-chain aliphatic aldehyde or ketone is derived from the name of the corresponding alkane of the same carbon count, by replacing the alkane's final -e with:

  • −al-al for an aldehyde, or
  • −one-one for a ketone.

Numbering the chain. For an aldehyde, the longest carbon chain is numbered starting from the carbonyl carbon itself — the −CHO-\text{CHO} carbon is always C-1. For a ketone, numbering instead begins from whichever end of the chain is nearer to the carbonyl group, so the carbonyl carbon receives the lowest possible locant. In both cases, substituents are cited as prefixes in alphabetical order, each with a numeral marking its position on the chain.

The same lowest-locant rule extends to cyclic ketones: the carbonyl carbon of the ring is always numbered C-1.

Aldehydes on a ring. When the −CHO-\text{CHO} group is attached to (rather than part of) a ring, the suffix -carbaldehyde is added after the full name of the cycloalkane, and the ring numbering starts from the ring carbon that carries the aldehyde group. The simplest aromatic aldehyde — a −CHO-\text{CHO} group directly on benzene — is systematically benzenecarbaldehyde, though IUPAC also accepts its familiar common name, benzaldehyde. Every other aromatic aldehyde is then named as a substituted benzaldehyde, with the ring position of each substituent numbered relative to the carbon bearing the −CHO-\text{CHO} group.

Multiple carbonyl groups. When a molecule carries more than one aldehyde group and the usual −al-al suffix cannot treat every −CHO-\text{CHO} group identically, the -carbaldehyde suffix is used instead, attached to the name of the parent chain — for example, a three-carbon chain bearing a −CHO-\text{CHO} group on every carbon is named propane-1,2,3-tricarbaldehyde rather than being forced into the −al-al pattern. …

Table 8.1Common and IUPAC Names of Some Aldehydes and Ketones
StructureCommon nameIUPAC name
Aldehydes
HCHOHCHOFormaldehydeMethanal
CH3CHOCH_3CHOAcetaldehydeEthanal
(CH3)2CHCHO(CH_3)_2CHCHOIsobutyraldehyde2-Methylpropanal
CH3C6H10CHOCH_3C_6H_{10}CHO (1,3-; the book draws the ring — see the illustration card)γ-Methylcyclohexanecarbaldehyde3-Methylcyclohexanecarbaldehyde
CH3CH(OCH3)CHOCH_3CH(OCH_3)CHOα-Methoxypropionaldehyde2-Methoxypropanal
CH3CH2CH2CH2CHOCH_3CH_2CH_2CH_2CHOValeraldehydePentanal
CH2=CHCHOCH_2{=}CHCHOAcroleinProp-2-enal
C6H4(CHO)2C_6H_4(CHO)_2 (o-; drawn in the book)PhthaldehydeBenzene-1,2-dicarbaldehyde
m-BrC6H4CHOBrC_6H_4CHO (drawn in the book)m-Bromobenzaldehyde3-Bromobenzenecarbaldehyde or 3-Bromobenzaldehyde
Ketones
CH3COCH2CH2CH3CH_3COCH_2CH_2CH_3Methyl n-propyl ketonePentan-2-one
(CH3)2CHCOCH(CH3)2(CH_3)_2CHCOCH(CH_3)_2Diisopropyl ketone2,4-Dimethylpentan-3-one
IUPAC naming examples of aldehydes and ketones as printed across pages 229-230: ethanal, 4-bromo-3-methylheptanal, 3-methylcyclopentanone, cyclohexanecarbaldehyde, pent-2-enal, 1-phenylpropan-1-one, 3-oxopentanal, 2,4-dimethylpentan-3-one, 4-nitrobenzenecarbaldehyde (also 4-nitrobenzaldehyde), and propane-1,2,3-tricarbaldehyde with the textbook's bracketed note on giving identical treatment to all aldehydic groups.
IUPAC naming examples of aldehydes and ketones as printed across pages 229-230: ethanal, 4-bromo-3-methylheptanal, 3-methylcyclopentanone, cyclohexanecarbaldehyde, pent-2-enal, 1-phenylpropan-1-one, 3-oxopentanal, 2,4-dimethylpentan-3-one, 4-nitrobenzenecarbaldehyde (also 4-nitrobenzaldehyde), and propane-1,2,3-tricarbaldehyde with the textbook's bracketed note on giving identical treatment to all aldehydic groups.

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your textbook's own diagram.

Redrawn from the NCERT page with the structures, printed labels (CH3, C, H, CH2, CH, CHO, H3C, NO2, OHC) and reagent placement exactly as the textbook prints them. Every element of this display was checked against the printed page during the sweep's blind-judge verification pass, so …

The four ring structures that Table 8.1 prints as drawings rather than formulas: gamma-methylcyclohexanecarbaldehyde (3-methylcyclohexanecarbaldehyde) with H3C and CHO on the two carbons flanking the top ring carbon, phthaldehyde (benzene-1,2-dicarbaldehyde) with two ortho CHO groups, m-bromobenzaldehyde (3-bromobenzaldehyde) with CHO and a meta bromine, and alpha-methylcyclohexanone (2-methylcyclohexanone) with the ring C=O and an adjacent methyl group.
The four ring structures that Table 8.1 prints as drawings rather than formulas: gamma-methylcyclohexanecarbaldehyde (3-methylcyclohexanecarbaldehyde) with H3C and CHO on the two carbons flanking the top ring carbon, phthaldehyde (benzene-1,2-dicarbaldehyde) with two ortho CHO groups, m-bromobenzaldehyde (3-bromobenzaldehyde) with CHO and a meta bromine, and alpha-methylcyclohexanone (2-methylcyclohexanone) with the ring C=O and an adjacent methyl group.

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your textbook's own diagram.

Redrawn from the NCERT page with the structures, printed labels (H3C, CHO, Br, O, CH3) and reagent placement exactly as the textbook prints them. Every element of this display was checked against the printed page during the sweep's blind-judge verification pass, so wh …