Organic Chemistry 2 · Naming organic compounds
Naming benzene derivatives: practice problems
24 problems, each with its worked solution. Open one to read every step, or filter by tag.
Classify 10
- Name an aminobenzene with a para halogenName a para-substituted aniline from the retained parent aniline (4-bromoaniline).
- Name a benzoic acid with a meta halogenName a substituted benzoic acid with the COOH carbon at C1 (3-bromobenzoic acid).
- Name an ortho dihalobenzeneName an ortho dihalobenzene with the alphabetical tie-break (1-bromo-2-chlorobenzene).
- Name a benzene with a CH2Cl groupName a benzene carrying a substituted methyl group with parentheses (benzyl chloride).
- Name a phenol with two chlorinesName a trisubstituted phenol with the OH carbon at C1 (2,4-dichlorophenol).
- Name a benzene with two meta chlorinesName a disubstituted benzene with identical substituents using numeric locants (1,3-dichlorobenzene).
- Name a para methyl-nitro benzeneName a disubstituted benzene with the alphabetical tie-break deciding C1 (1-methyl-4-nitrobenzene).
- Name a secondary alcohol bearing a benzene ringName an alcohol whose chain carries a phenyl group (1-phenylethan-1-ol).
- Name a benzene ring with a three-carbon chainName a monosubstituted benzene with an unbranched alkyl group (propylbenzene).
- Name a benzene with Br, Cl and CH3Name a trisubstituted benzene by lowest locants then alphabetical order (1-bromo-2-chloro-4-methylbenzene).
Compare 2
- Rank benzene locant sets by first point of differenceCompare locant sets term by term at the first point of difference.
- Rank retained benzene parents by seniorityRank the retained parents aniline, phenol, benzaldehyde and benzoic acid by principal-group seniority.
Calculate 2
- Count the dibromobenzene isomersCount the positional isomers of a disubstituted benzene with two identical groups (dibromobenzene).
- Count the trichlorobenzene isomersCount the positional isomers of a trisubstituted benzene with three identical groups (trichlorobenzene).
Find the error 4
- Diagnose prefix order in a meta ethyl-nitro areneCorrect a name that cites prefixes out of alphabetical order (1-ethyl-3-nitrobenzene).
- Diagnose o,p letters on a three-group areneCorrect an o/m/p name used for a trisubstituted benzene (1-methyl-2,4-dinitrobenzene).
- Diagnose a hydroxy-prefix name for a methyl areneExplain why a hydroxybenzene is named from the retained parent phenol (4-methylphenol).
- Diagnose a chain-parent name for an arylethyl bromideCorrect a name that makes the chain the parent instead of the ring ((2-bromoethyl)benzene).
Interpret the evidence 4
- Pick the structure of a para diethylareneMatch a disubstituted benzene name to its structure (1,4-diethylbenzene).
- Pick the structure of a para methoxy phenolMatch a substituted phenol name to its structure (4-methoxyphenol).
- Pick the structure of a primary phenyl alcoholMatch a phenyl-substituted alcohol name to its structure (2-phenylethan-1-ol).
- Pick the structure of a tribromo anilineMatch a trisubstituted aniline name to its structure (2,4,6-tribromoaniline).
Explain why 2
- Why o, m and p stop at two substituentsExplain why ortho, meta and para are used only for disubstituted benzenes.
- Why toluene but 1-methyl-4-nitrobenzeneExplain why toluene is a preferred name for C6H5CH3 but substituted toluenes are named as methylbenzenes.
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