Ch. 4 - Alkanes and CycloalkanesSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

In chemistry, every single molecule needs a unique name. We can’t have two molecules with the same name or that would get super confusing! For this, we use IUPAC nomenclature. 

Alkane Nomenclature Overview

Concept #1: The different parts of an IUPAC name 

Basically there are 4 different parts to naming most molecules:

  • The Root or Parent Chain (this tells us about overall chain length)
  • Modifiers (tells us what functional groups are attached to the chain)
  • Substituents (tells us about what is branching off that chain)
  • Numerical Locations (tells us where those branches are)
Alkane Prefixes

Concept #2: Learning Alkane Prefixes up to 12 Carbons in Length 

Memorizing sucks, I get it. But unfortunately this is something you’re just gonna have to remember. Not all professors will make you memorize all 12 so check with your professor to figure out how many you need to know!

IUPAC Alkane Naming Rule #1

Concept #3: Naming the root chain 

Remember, if there is a TIE between two chains of equal length, go with the chain that gives the MOST substituents!

IUPAC Alkane Naming Rule #2

Now we know the length of the root chain, but nothing else! We need to determine which carbon gets the “1” location. 

Concept #4: How to determine the direction of the root chain 

  • Start numbering the root chain starting from the closest substituent
    • If there is a tie between locations, compare the locations of the next substituents
    • If there is STILL a tie between ALL locations, decide using alphabetical order.

The key here is to get the lowest numbers possible for ALL of your locations (at least for now). Now give it a shot by yourself with these examples!

Example #1: Name the longest carbon chain and determine the direction of the root chain 

Example #2: Name the longest carbon chain and determine the direction of the root chain 

If you got this one wrong, don’t worry too much. You’ve got plenty more chances to nail this. 

IUPAC Alkane Naming Rule #3

So we know the length and direction of the root chain, which is great. But if there are ANY branches on this chain, we need to name those too.

 

P.S. The term “substituent” is just a nerdy word for a “branch”. 

Concept #5: How to identify and locate branches (substituents) 

NOTE: Alkane substituents require a “-yl” suffix to indicate that they are a branch! (i.e. ethane becomes ethyl). 

Example #3: Name the root chain, determine the direction of the root chain and then identify & locate all substituents 

Sick job! We’re getting closer to fully naming these guys. 

IUPAC Alkane Naming Rule #4 and #5

Now we have all the pieces we need to name most alkanes, but we need to work on our formatting! Chemists are surprisingly analytical making sure all your commas and numbers are in the right place.

Concept #6: Proper name ordering and punctuation 

In short:

  • Always name your substituents in alphabetical order
  • Commas separate numbers from numbers, and dashes separate numbers from letters (i.e. 1,2-dimethyl)

Example #4: Provide the IUPAC name for the following alkane

Does this make sense? You just learned how to name simple alkanes. Give yourself a pat on the back!

Additional Problems
What is the correct name of the alkane shown? A. 3,6-diethyl-2,2,5-trimethylheptane B. 3-ethyl-2,2,5,6-tetramethyloctane C. 3-tert-butyl-5,6-dimethyloctane D. 5,6-dimethyl-3-tert-butyloctane E. None of the above
Identify the name of the parent for each of the following compounds:
Identify the name of the parent for each of the following compounds:
Identify the name of the parent for each of the following compounds:
Identify the name of the parent for each of the following compounds:
Each of the structures in the previous problem has one or more substituents connected to the parent. (a) Identify the name of each substituent in 4.39a.
Each of the structures in the previous problem has one or more substituents connected to the parent. (c) Identify the name of each substituent in 4.39c.
What is the systematic name for each of the following  compounds:
Give systematic IUPAC names for each of the following:  
Write structural formulas and give the IUPAC names for the nine alkanes that have the molecular formula C7H16 .  
Give systematic IUPAC names for each of the following:  
Each of the following names are incorrect. Provide the correct name and structure. 2-ethylhexane     2-methyl-3-ethyl-octane  
From among the 18 constitutional isomers of C 8H18, write structural formulas, and give the IUPAC names for those that are named as derivatives of (a) Heptane
Give systematic IUPAC names for each of the following:  
From among the 18 constitutional isomers of C 8H18, write structural formulas, and give the IUPAC names for those that are named as derivatives of (b) Hexane
From among the 18 constitutional isomers of C 8H18, write structural formulas, and give the IUPAC names for those that are named as derivatives of (c) Pentane 
Pristane is an alkane that is present to the extent of about 14% in shark liver oil. Its IUPAC name is 2,6,10,14-tetramethylpentadecane. Write its structural formula. 
What is a correct IUPAC name for this compound? A) 1,1,1,6-tetramethylheptane B) 1-tert-butyl-4-isopropylbutane C) 2,2,7-trimethyloctane D) 1-tert-butyl-4-isopropyloctane
All the parts of this problem refer to the alkane having the carbon skeleton shown.   (a) What is the molecular formula of this alkane? 
All the parts of this problem refer to the alkane having the carbon skeleton shown.   (b) What is its IUPAC name? 
All the parts of this problem refer to the alkane having the carbon skeleton shown.   (c) How many methyl groups are present in this alkane? Methylene groups? Methine groups? 
All the parts of this problem refer to the alkane having the carbon skeleton shown.  (d) How many carbon atoms are primary? Secondary? Tertiary? Quaternary? 
Give the IUPAC name for each of the following compounds: (a) CH3(CH2)25CH3 
Give the IUPAC name for each of the following compounds: (b) (CH3)2CHCH2(CH2)14CH3
Give the IUPAC name for each of the following compounds: (c) (CH3CH2)3CCH(CH2CH3)2
Give the IUPAC name for each of the following compounds:  
Write the structure and give the IUPAC systematic name of an alkane or cycloalkane with the formulas (a) C8H18 that has only primary hydrogen atoms.  
Draw each of the following compounds: (a) 2,2,4-Trimethylpentane
Give the IUPAC name for each of the following compounds:
Write the structure and give the IUPAC systematic name of an alkane or cycloalkane with the formulas (b) C6H12 that has only secondary hydrogen atoms.  
Give the IUPAC name for each of the following compounds:
Write the structure(s) of the simplest alkane(s), i.e., one(s) with the fewest number of carbon atoms, wherein each possesses primary, secondary, tertiary, and quaternary carbon atoms. (A quaternary carbon is one that is bonded to four other carbon atoms.) Assign an IUPAC name to each structure.  
Write a structural formula for each of the following compounds:  (b) 4 -tert -Butyl-3-methylheptane
Using the method outlined in Section 2.13, give an IUPAC name for each of the following alkyl groups, and classify each one as primary, secondary, or tertiary:  (a) CH3(CH2)10CH2 —
Using the method outlined in Section 2.13, give an IUPAC name for each of the following alkyl groups, and classify each one as primary, secondary, or tertiary:
Using the method outlined in Section 2.13, give an IUPAC name for each of the following alkyl groups, and classify each one as primary, secondary, or tertiary:  (c) —C(CH2CH3)3 
Using the method outlined in Section 2.13, give an IUPAC name for each of the following alkyl groups, and classify each one as primary, secondary, or tertiary:  
Provide an acceptable IUPAC name for the following three molecules. Do not designate R or S for this but you need to indicate cis or trans if appropriate.
Using the method outlined in Section 2.13, give an IUPAC name for each of the following alkyl groups, and classify each one as primary, secondary, or tertiary:  
The 2004 IUPAC names for alkyl groups are derived from the alkane having the same carbon chain as the alkyl group. The -e ending of that alkane is replaced by - yl, and the chain is numbered from the end that gives the carbon at the point of attachment its lower number. This number immediately precedes the - yl ending and is bracketed by hyphens.    Name the C4H9 alkyl groups according to this system. 
Write the structural formula of a compound of molecular formula C 4H8Cl2 in which (a) All the carbons belong to methylene groups 
Write the structural formula of a compound of molecular formula C 4H8Cl2 in which  (b) None of the carbons belong to methylene groups 
Female tiger moths signify their presence to male moths by giving off a sex attractant (pheromone). The sex attractant has been isolated and found to be a 2-methyl-branched alkane having a molecular weight of 254. What is this material? 
Write the IUPAC name for the following strucutre. Ignore R and S while naming.
Draw a line–angle structure for 3–Ethyl–4–methylhexane.
Draw a line–angle structure for 4,5–dipropyloctane.
Draw the structure described by this name:  2-Ethyl-3-methylpentane    Which statement below is  TRUE? A. The name  2-ethyl-3-methylpentane  is CORRECT B. The correct name of this molecule is  3,4-dimethylhexane C. The correct name of this molecule is  4-ethyl-3-methylpentane D. The correct name of this molecule is  2,4-dimethylhexane E. No statement above is true
Give the IUPAC names of each of the following alkanes. 
Draw the structure described by this name:  5-Neopentyloctane   Which statement below is  TRUE? A. The name  5-neopentyloctane is CORRECT B. The correct name of this molecule is  4-neopentyloctane C. The correct name of this molecule is  2,2-dimethyl-4-butylheptane D. The correct name of this molecule is  2,2-dimethyl-4-propyloctane E. No statement above is true.
Each of the structures in the previous problem has one or more substituents connected to the parent.(b) Identify the common name and the IUPAC name of the complex substituent in 4.39b.
Each of the structures in the previous problem has one or more substituents connected to the parent.(d) Identify the common name and the IUPAC name of the complex  substituent in 4.39d.
What is the IUPAC name of the following molecule? A)        4-secbutyl-4,8-dimethyldecane B)        3,4,8-trimethyl-4-propyldecane C)        3,7,8-trimethyl-7-propyldecane D)        4,8-dimethyl-4(1-methylethyl)-decane
Name the following molecule (using IUPAC nomenclature):
What is the IUPAC name of the following compound?
What is the IUPAC name of the compound shown? 
What is the IUPAC name for the following compound?
What is the IUPAC name for the compound shown below?
Draw the following molecule according to the IUPAC rules: IUPAC Name: 4-isopropyl-2-methyheptane 
Draw the structure of 4-isopropyl-2,6,8-trimethyldecane in the window below.
What is the IUPAC name for the compound shown below?
What is the IUPAC name for the following compound? Enter the name of the molecule. 
Spell out the full name of the compound.
What is the IUPAC name for the compound shown below?
What is the IUPAC name for the compound shown below?
The following names are incorrect. Draw the structure of the compound and provide the correct IUPAC name. Molecule #1: tripropylmethane 
What is the IUPAC name for the compound shown below?
The correct IUPAC name for the compound shown below is _____. a. 2, 2, 4-trimethyl-7-propylnonaneb. 7-ethyl-2, 2, 4-trimethyldecanec. 3-propyl- 6, 8, 8-trimethylnonaned. 4-ethyl-7, 9, 9-trimethylnonanee. 4-ethyl-7, 9, 9-trimethyldecane 
Which of the following is a correct IUPAC name?a. 1-ethylpentaneb. 2-ethylpentanec. 3-ethylpentaned. none, they are all incorrect 
Which of the following is not a correct IUPAC name for an alkene?a. 2-methyl-1-buteneb. 2-methyl-3-butenec. 2-methyl-2-butened. none, these are all correct IUPAC names 
What is the IUPAC name for the following compound? 
What is the IUPAC name for the following alkane? 
What is the IUPAC name for the following alkane? 
What is the IUPAC name for the following alkane? 
What is the IUPAC name for the following alkane? 
Give the IUPAC name for the chemical in the attached image.a. 2,2,5,6-tetraethylhexaneb. 2,2,5-triethyloctanec. 3,6-diethyl-3-methylnonaned. 3-ethyl-3-methyl-6-propyldecane 
Give IUPAC names for the following compound.
What is the IUPAC name of  
What is the IUPAC name for the compound shown below?  Spelling and punctuation count!
What is the IUPAC name for the compound shown below?
The IUPAC name for the compound in the attached picture is _____.a. 3-ethylbutaneb. 2-methylbutanec. 3-methylpentaned. 2-ethylbutane  
Give IUPAC name for the following compound.
Spell out the full name of the compound.
Spell out the full name of the compound.
Give the IUPAC name for the following alkane.
Write the IUPAC name for the compound below. Be sure to use correct punctuation. Keep the information page open for guidance and for use with feedback.Accepted names for branched alkyl groups are isopropyl, isobutyl, sec-butyl, and tert-butyl.Do not use italics. The IUPAC name is
Spell out the full name of the compound.
Spell out the full name of the compound.
Give IUPAC name for the following compound. 
Spell out the full name of the compound.
Write the IUPAC name for the compound below. Be sure to use correct punctuation. Keep the information page open for guidance and for use with feedback. Accepted names for branched alkyl groups are isopropyl, isobutyl, sec- butyl, and tert-butyl.Do not use italics.
Give the IUPAC name for the following compound. Be sure to answer all parts
Branches within branches.The IUPAC name of this compound is _____. (omit italics)
What is the IUPAC name for the compound shown below?
Spell out the full name of the compound.
Spell out the full name of the compound.
What is the IUPAC name of the following compound?
What is the IUPAC name for the compound shown below?
What is the correct IUPAC name of this compound? Select one:a. 4-ethyl-4-methylhexaneb. 3-ethyl-3-methylhexanec. 4-methyl-4-ethylhexaned. 3-methyl-3-ethylhexane 
What is the IUPAC name for the compound shown below? 
What is the IUPAC name for the compound shown below?
Give IUPAC name for the following compound. 
Give the IUPAC name for the following compound.