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

Bicyclic rings possess multi-ring systems within the same molecule

Types of Bicyclic Molecules

Basically there two general categories of bicyclics:

Concept #1: The two types of bicyclic molecules 

Bridged Bicyclic Nomenclature (Three Rings)
  • The bridgehead atom (one of the circled ones) must always be in the “1” position
  • The name is formatted as bicyclo[ringsize1.ringsize2.ringsize3]alkane

Concept #2: How to name a bridged bicyclic 

Fused Bicyclic Nomenclature (Two Rings)

Concept #3: How to name a fused bicyclic 

*Error: The name of this molecule was misstated in the video. Please refer to the name below (pentane)!

Awesome job! These are some of the hardest molecules to name, so if you got them, you’re ahead of the curve. 

Additional Problems
For each of the following structures provide the IUPAC name.
What is the systematic name for each of the following  compounds:
What is the systematic name for each of the following  compounds:
Write a bond-line formula for each of the following compounds: (m) Bicyclo[2.2.2]octane  
Write a bond-line formula for each of the following compounds: (n) Bicyclo[3.1.1]heptane  
For each of the following IUPAC names draw the skeletal structure in the space provided below. [3.2.0]bicycloheptane       cis-1,3-diethylcyclopentane  
Give systematic IUPAC names for each of the following:  
Give systematic IUPAC names for each of the following:  
Give systematic IUPAC names for each of the following:  
Draw each of the following compounds: (c) 2,2,4,4-Tetraethylbicyclo[1.1.0]butane
Write structures for the following bicyclic alkanes: (a) Bicyclo[1.1.0]butane  
Write structures for the following bicyclic alkanes: (b) Bicyclo[2.1.0]pentane  
Using the rules found in this chapter, give systematic names for the following or indicate that more rules need to be provided:  
Using the rules found in this chapter, give systematic names for the following or indicate that more rules need to be provided:  
Provide a systematic IUPAC name for the molecule below. Remember to include the absolute configuration (R/S) of all the chirality centers in the molecule.
For each of the following structures provide the IUPAC name.
Provide the IUPAC name for the following structure.
Draw the structure for the following IUPAC name. bicyclo[4.3.1]decane
What is the IUPAC name of the following compound? (a) 1 - methylbicyclo[2.2.1]heptane  (b) 2 - methylbicyclo[2.2.1]heptane  (c) 3 - methylbicyclo[2.2.1]heptane  (d) 4 - methylbicyclo[2.2.1]heptane 
(a) Write the structure of 2,2-dichlorobicyclo[2.2.1]heptane.