IUPAC Nomenclature Practice Problems

This is a set of practice problems on naming organic compounds. The examples cover the nomenclature of alkanes, bicyclic compounds, alkenes, alkynes, alcohols, alkyl halides, aromatic compounds, aldehydes and ketones, amines, ethers, and carboxylic acid derivatives such as nitriles, esters, and amides. Some of the examples are also compounds with multiple functional groups, in which case you need to know the priority of the functional groups. This allows us to determine whether the functional groups are named using a prefix or a suffix. 

 

Check this 69-question, Multiple-Choice Quiz with a 2-hour Video Solution on naming alkanes, alkyl halides, alkenes, alkynes, aromatic compounds, alcohols, aldehydes, ketones, and compounds containing multiple functional groups. 

 

 

The Nomenclature of Alkanes

  1. Provide a systematic name for each of the following compounds:

 

 

2. Draw the bond-line structure for each of the following molecules:

a) 4-ethyl-5-isopropyl-3-methyloctane

b) 1-ethyl-4-methyl-2-propylcyclopentane

c) 5-(sec-butyl)-8-isopropyl-3,4,9-trimethylundecane

d) 6-(sec-butyl)-7-ethyl-3,4-dimethyldecane

e) 3-ethyl-4,5-dimethylheptane

f) 4-ethyl-3-isopropyl-1,1-dimethylcyclohexane

g) 6,6-diethyl-3,5,5-trimethylnonane

h) 4-(sec-butyl)-3,3,5,5-tetramethylheptane

Answers

 

The Nomenclature of Bicyclic Compounds

Name each of the following bicyclic compounds:

 Answers

 

The Nomenclature of Alkyl Halides

Give a systematic name for each of the following compounds:

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The Nomenclature of Alkenes

Name the following alkenes according to the IUPAC nomenclature rules. Determine if the configuration of the double bond is E or Z and include it in the name:

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The Nomenclature of Alkynes

Provide a systematic name for each of the following alkynes:

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The Nomenclature of Alcohols

Provide an IUPAC name for each of the following alcohols: Indicate the stereochemistry where needed.

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The Nomenclature of Aromatic Compounds

Give an acceptable IUPAC name for each molecule according to the nomenclature of aromatic compounds. For some compounds, there may be more than one acceptable name.

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The Nomenclature of Aldehydes and Ketones

Assign a systematic IUPAC name to each of the following aldehydes and ketones:

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The Nomenclature of Carboxylic Acid Derivatives Containing Other Functional Groups

Using the priority of functional groups, name each of the following compounds containing a carboxylic acid derivative:

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