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Advanced level organic chemistry PART 14.7: Aromatic structural isomers of molecular formula C8H8O2

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Doc Brown's Advanced Chemistry: Part 14.7

Aromatic structural isomers of molecular formula C8H8O2

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See also Examples of the effects of isomerism on the similarity or difference in the physical and chemical properties of structural isomers

Selected aromatic structural isomers of molecular formula C8H8O2 (Mr = 136)

There are at least 18 (more?) aromatic ring molecules with the molecular formula C8H8O2

(1) to (3) 2-methylbenzoic acid  isomers of C8H8O2 structural formula 2-methylbenzoic acid molecular structure advanced organic chemistry ,  3-methylbenzoic acid  isomers of C8H8O2 structural formula 3-methylbenzoic acid molecular structure advanced organic chemistry , 4-methybenzoic acid  isomers of C8H8O2 structural formula 4-methylbenzoic acid molecular structure advanced organic chemistry

(4) isomers of molecular formula C8H8O2 molecular mass 136 , isomers of molecular formula C8H8O2 molecular mass 136 , isomers of molecular formula C8H8O2 molecular mass 136 , isomers of molecular formula C8H8O2 molecular mass 136 , methyl benzoate, an ester of benzoic acid

(5) to (7) Three isomeric bifunctional aromatic molecules with a ketone and phenol functional groups.

The very abbreviated structural formula is: HO-C6H4-CO-CH3

e.g.  isomers of molecular formula C8H8O2 molecular mass 136 IUPAC preferred name is 1-(2-hydroxyphenyl)ethanone

(8) the ester phenyl ethanoate , CH3COOC6H5isomers of molecular formula C8H8O2 molecular mass 136

(9) C6H5-CO-CH2OH, has a ketone and an aliphatic primary alcohol functional groups.

(10) C6H5-CH2-COOH, phenylethanoic acid, has an aliphatic carboxylic acid functional group.

(11) to (13) Three isomeric bifunctional aromatic molecules with an aromatic aldehyde and aliphatic primary alcohol functional group.

The very abbreviated structural formula is: HO-CH2-C6H4-CHO  and these would be named

(14) to (16) Three isomeric bifunctional aromatic molecules with an aldehyde and an ether functional groups.

The very abbreviated structural formula is: CH3-O-C6H4-CHO

2-methoxybenzaldehyde, 3-methoxybenzaldehyde and 4-methoxybenzaldehyde

(17) C6H5-CH(OH)-CHO, 2-hydroxy-2-phenylethanal,

a bifunctional aromatic molecule with an aliphatic aldehyde and aliphatic secondary alcohol functional groups.

This has a chiral (asymmetric) carbon atom and will exhibit R/S stereoisomerism - R/S optical isomers (enantiomers)

(18) C6H5-C(OH)=CH-OH, 1-phenylethene-1,2-diol

a bifunctional aromatic molecule with an aliphatic alkene and alcohol functional groups.

This has a C=C double bond attached to four different groups and will exhibit E/Z stereoisomerism - a pair E/Z isomers (cis/trans in old notation).


Associated links

Index of sets of isomers for a given molecular formula

The molecular structure & Naming of AROMATIC Compounds, including isomers

INDEX of ALL revision notes on the chemistry of AROMATIC COMPOUNDS

Isomerism: introduction, structural isomerism - chain, positional, functional group, tautomerism

Stereoisomerism: introduction, definition, priority rules, E/Z isomerism (cis/trans isomerism)

Stereoisomerism - R/S isomerism (optical isomerism) - definition - examples explained

index for all isomerism pages

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