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IUPAC Nomenclature Practice Problems

The following questions are organized somewhat by functional group (as many organic courses introduce nomenclature one functional group at a time). The index below will take you to the beginning of questions that focus on a particular functional group, or you may page through the document as you like.

Question 1:Basic Hydrocarbon NomenclatureQuestion 2:Unsaturated Hydrocarbon NomenclatureQuestion 3:Nomenclature from Condensed FormulasQuestion 4:Nomenclature of Aromatic HydrocarbonsQuestion 5:Nomenclature of Halogen CompoundsQuestion 6:Nomenclature of AlcoholsQuestion 7:Nomenclature of Aldehydes & KetonesQuestion 8:Nomenclature of Carboxylic Acids

If you are asked to write a IUPAC name for a compound, pay careful attention to the syntax of this nomenclature system. For example, commas and dashes must be used in precisely the correct manner, and extra spaces must be avoided. Spelling must also be absolutely correct. Computers (and some instructors) are unforgiving when it comes to judging the names you submit.

Question 1: Basic Hydrocarbon Nomenclature

Part A: Enter the number of carbons indicated by each of the following root names in the designated answer box.

Root Number of Carbons Root Number of Carbons
Hexane Propane
Butane Pentane
Nonane Heptane
Decane Ethane

Part B: The line formula for a branched alkane is shown below.

Line structure of a branched alkane, C10H22, with a seven-carbon main chain bearing two alkyl substituents What is the molecular formula of this compound? CH
How many carbon atoms are in the longest chain?
How many alkyl substituents are attached to this chain?

Part C: The line formula for another branched alkane is shown below.

Line structure of 3,4-diethyl-2-methylhexane, a branched alkane In the IUPAC system what is the root or base name of this compound?
How many alkyl substituents are attached to the longest chain?
Give the IUPAC name for this compound.

Part D: The formula for a substituted cycloalkane is shown below.

Substituted cyclohexane ring with two methyls and an ethyl group; ring carbons labeled a through f In the IUPAC system what is the root or base name of this compound?
How many alkyl substituents are attached to the ring?
In numbering the ring, which carbon (a-f) is #1?
In numbering the ring, which carbon (a-f) is #2?
Give the IUPAC name for this compound.

Part E: The formula for another cycloalkane derivative is shown below.

Cyclopentane ring bearing a cyclopropyl group and a propyl group on the same carbon Give the IUPAC name for this compound.




Question 2: Unsaturated Hydrocarbon Nomenclature

Part A: The line formula for a branched alkene is shown below.

Line structure of a branched alkene, 2,5-dimethyl-3-propyl-2-hexene What is the molecular formula of this compound? CH
How many carbon atoms are in the longest chain, ignoring the double bond?
What is the longest chain incorporating both carbons of the double bond?
How many substituents are on this chain?
Give the IUPAC name for this compound.

Part B: The line formula for a cyclic alkene is shown below.

Cycloheptene ring with an ethyl and two methyl substituents; ring carbons labeled a through g In numbering the ring, which carbon (a-g) is #1?
Give the IUPAC name for this compound.

Part C: Name the following compounds according to the IUPAC system:

(1) Cyclopentene ring bearing a methyl group and a vinyl group Enter the IUPAC name
(2) Conjugated diene, 2,3-diethyl-4-methyl-1,3-pentadiene Enter the IUPAC name
(3) Line structure of 6,6-dimethyl-2-heptyne, an internal alkyne Enter the IUPAC name
(4) Cyclohexane ring with a pent-1-en-3-ynyl chain, 5-cyclohexyl-1-penten-3-yne Enter the IUPAC name
(5) Cyclooctadiene ring bearing an allyl group, 6-allyl-1,4-cyclooctadiene Enter the IUPAC name
(6) Cyclopentene ring with phenyl groups at positions 1 and 4, 1,4-diphenylcyclopentene Enter the IUPAC name




Question 3: Hydrocarbon Nomenclature from Condensed Formulas

Part A: (CH3)2CHCH(C2H5)CH2CH2CH3

Give the IUPAC name for this compound.

Part B: CH2=C(C2H5)CH2CH2CH3

Give the IUPAC name for this compound.

Part C: (CH3)2C=CHC(C2H5)=CH2

Give the IUPAC name for this compound.

Part D: CH3C≡CCH(C2H5)2

Give the IUPAC name for this compound.

Part E: (CH3)3CC≡CCH2CH=C(CH3)2

Give the IUPAC name for this compound.




Question 4: Aromatic Hydrocarbons

Name the following compounds according to the IUPAC system:

(1) Benzene ring with an ethyl group and an allyl group on adjacent carbons, 1-allyl-2-ethylbenzene Enter the IUPAC name
(2) Naphthalene, two fused benzene rings Enter the IUPAC name
(3) Benzene ring with two adjacent methyl groups, ortho-xylene (1,2-dimethylbenzene) Enter the IUPAC name
(4) Benzene ring with a vinyl group, styrene (vinylbenzene) Enter the IUPAC name
(5) Benzene ring with three methyl groups at the 1,3,5 positions, mesitylene Enter the IUPAC name




Question 5: Halogen Substituted Compounds

Name the following compounds according to the IUPAC system:

(1) Branched bromoalkane, 3-bromo-2,5-dimethylhexane Enter the IUPAC name
(2) Highly branched dichlorodecane, 7,7-dichloro-4-ethyl-3,3,8-trimethyl-4-propyldecane Enter the IUPAC name
(3) Cyclohexadiene ring with a bromine and a methyl group, 1-bromo-5-methyl-1,4-cyclohexadiene Enter the IUPAC name
(4) Chlorinated enyne, 2-chloro-1-penten-4-yne Enter the IUPAC name
(5) Benzene ring with bromo, ethyl, and methyl substituents, 1-bromo-3-ethyl-5-methylbenzene Enter the IUPAC name




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