Ch. 4 - Alkanes and CycloalkanesWorksheetSee 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

IUPAC naming is awesome because it’s pretty easy to master. But unfortunately there are some non-IUPAC names we need to know for this course. These apply mostly to weird looking substituents. Let's take a look.

Concept #1: Understanding Non-IUPAC Substituents 

Quick note: "n" stands for normal :)

Pro Tip: For the butyl groups, you can use the number of substituent carbons attached to it to determine the prefix on the name. (i.e. Butyl with 2 carbons branching off of it is a secondary, or sec-butyl)

Example #1: Name the following alkane

Remember to always apply IUPAC rules 1-5 before deciding if a substituent is common or not! Let’s try another. 

Example #2: Name the following alkane

Iso, just like cylo and neo should be considered when alphabetizing. However, prefixes such as tert-, tetra-, sec-, tri-, di- and so forth can be ignored

Awesome. Now you know how to name pretty much any branched alkane. Party time!

Additional Problems
What is the correct name of the alkane shown below? A. 2-Ethyl-3-isopentyl-3-propylhexane B. 5-sec-Butyl-6-ethyl-2-methylnonane C. 2-Methyl-5-sec-butyl-6-ethylnonane D. 5-Ethyl-4-isopentyl-3-methyloctane E. None of the above
Give systematic IUPAC names for each of the following:  
The name sec-butyl alcohol defines a specific structure but the name sec-pentyl alcohol is ambiguous. Explain.  
Write a structural formula for each of the following compounds: (a) 6-Isopropyl-2,3-dimethylnonane
Provide a structural formula for  5-(sec-butyl)-8-ethyl-3-methyldecane. Please show a complete structural formula showing all atoms and all bonding valence electrons.
Grandisol is one component of the sex attractant of the boll weevil. Write a structural formula for grandisol given that R in the structure shown is an isopropenyl group.
For the two questions below, an incorrect name has been given for an alkane. To answer these questions, you will need to draw the structure described by the incorrect name. Once you have drawn the structure, use the nomenclature rules to assign the correct name to the alkane.   The incorrect name is: 2-Methyl-5-tert-butylheptane What is the correct name of this alkane? A. 5-Ethyl-2,6,6-trimethylheptane B. 3-Ethyl-2,2,6-trimethylheptane C. 5-tert-Butyl-2-methylheptane D. 4-tert-Butylisooctane E. None of the above   The incorrect name is: 4-Butyl-2,2-dimethyloctane What is the correct name of this alkane? A. 5-Butyl-7,7-dimethyloctane B. 2,2-Dimethyl-4-butyloctane C. 5-Neopentylnonane D. 5-tert-Butylnonane E. None of the above
Draw a line–angle structure for 5–tert–butyl–8–isobutyldodecane.
Draw the line structure of the following compound. 6-Isopropyl-2,3-dimethylnonane
Draw a line–angle structure for 5–sec–butyl–3,3–diethyl–4–isopropylnonane.
Give the IUPAC name for the following hydrocarbon.
Alkyl isothiocyanates are compounds of the type RN=C=S. Write a structural formula for allyl isothiocyanate, a pungent-smelling compound isolated from mustard.
Name the following alkane. 
What is the IUPAC name for the compound shown below? Spelling and punctuation count!
What is the IUPAC name for this alkane? (a) 2-ethyl-3-methylpentane (b) 4-ethyl-3-methylpentane (c) 3, 4-dimethylhexane (d) 2, 3-diethylbutane (e) octane
What is the IUPAC name for the compound shown below? 
Branches within branches.The IUPAC name of this compound is _____________. (omit italics)
What is the IUPAC name for (a) 1-methylbutane. (b) 4-methylbutane. (c) pentane. (d) butane. (e) hexane. 
Give the IUPAC name for the following compound.
Give the IUPAC name for the following compound.
What is the name of 3, 3-dimethylbutane 2, 2-dimethylbutane dimethylbutane 2-dimethylbutane, hexane
Select the correct name for the following compound. 1, 1, 3-triethyl-2-methylbutane 3-ethyl-4, 5-dimethylheptane 2, 4-diethyl-3-methylhexane 1, 1 -diethyl-2, 3-dimethylpentane none of the above