Organic Nomenclature 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.

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.

RootNumber of Carbons RootNumber of Carbons
Hexane Propane
Butane Pentane
Nonane Heptane
Decane Ethane

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

  What is the molecular formula of this compound? C H
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.

  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.

  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.

  Give the IUPAC name for this compound.





 

 

Question 2: Unsaturated Hydrocarbon Nomenclature

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

  What is the molecular formula of this compound? C H
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.

  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)   Enter the IUPAC name
(2) Enter the IUPAC name
(3) Enter the IUPAC name
(4) Enter the IUPAC name
(5) Enter the IUPAC name
(6) 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)   Enter the IUPAC name
(2) Enter the IUPAC name
(3) Enter the IUPAC name
(4) Enter the IUPAC name
(5) Enter the IUPAC name





 

 

Question 5: Halogen Substituted Compounds

Name the following compounds according to the IUPAC system:

(1)   Enter the IUPAC name
(2) Enter the IUPAC name
(3) Enter the IUPAC name
(4) Enter the IUPAC name
(5) Enter the IUPAC name





 

This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.