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

Since double bonds and rings can’t rotate, we need different names for the different arrangements they can create. 

Concept #1: How to name different types of double bonds or rings 

Two groups coming off the same carbon never have a cis/trans relationship. In case you are wondering, they are called geminal (you don’t need to know this yet.) 

E/Z Nomenclature

The cis/trans nomenclature system is awesome, but it breaks down with multisubstituted alkenes. 

Concept #2: Why we need to use the E/Z naming system 

So the E/Z naming system allows us to name tri- and tetra- substituted alkenes.

The difference between E and Z

Concept #3: What does E and Z stand for? 

Using the periodic table to assign priorities, trans = E, and cis = Z

Example #1: Assign an (E) – (Z) designation to the following alkenes if applicable  

Example #2: Assign an (E) – (Z) designation to the following alkenes if applicable

Great! Now let’s combine this with what we’ve learned about functional groups (alkyl halides and alcohols) to name some more complex molecules. 

Practice: Determine the IUPAC name of the following molecule 

This was a great example of how the root chain must always have the functional group within it, even if it is shorter!

Practice: Determine the IUPAC name of the following molecule 

Hope you don’t hate me for throwing two alcohols in there! This is great practice though. 

Additional Problems
Which structure shown below represents ( Z )-3,5-dichloro-3-hexen-1-yne?
Draw the structure of the following molecule. Make sure your strucuture show s the stereochemistry of the alkene.  (2Z,4Z,6Z)-2,4-dimethyl-2,4,6-heptatrien-1-ol
Determine the IUPAC name for the compound given below.  a) ortho-bromocyclohexanol b) endo-2-bromocyclohexanol c) cis-2-bromocyclohexanol d) trans-2-bromocyclohexanol
For the following structure, identify each pair of carbons which share a double bond and designate the alkene moiety as E or Z.
Provide the IUPAC name for the compound given below.  a) (E)-3,5-dimethyl-2-hexene b) (Z)-3,5-dimethyl-2-hexene c) (Z)-1,2-dimethyl-2-isobutylethylene d) (E)-3,5,5-trimethyl-2-pentene
Which of the following is ( E )-1,2-dichloro-2-pentene?
Which of the following is ( Z )-3,5-dimethyl-3-nonene?  
What is the proper IUPAC name for the compound below? a) (Z)-5-ethyl-4-hexen-2-ol b) (Z)-3-methyl-3-hepten-6-ol c) (E)-5-methyl-4-hepten-2-ol d) (Z)-5-methyl-4-hepten-2-ol
Using the rules found in this chapter, give systematic names for the following or indicate that more rules need to be provided:  
Write structural formulas for each of the following: (e) (Z)-3-Methyl-2-hexene
Please draw or name the corresponding molecular structures. Indicate stereochemistry (R/S, E/Z) where applicable.
Write structural formulas for each of the following: (f) (E)-3-Chloro-2-hexene
Please draw or name the corresponding molecular structures.  (Z)-3-methylhept-3-ene
 For each of the following IUPAC names draw the skeletal structure in the space provided below.
(a) The sex attractant of the Mediterranean fruit fly is ( E )-6-nonen-l-ol. Write a structural formula for this compound, showing the stereochemistry of the double bond. 
Write bond-line formulas for each of the following naturally occurring compounds, clearly showing their stereochemistry Geraniol: a hydrocarbon with a rose-like odor present in the fragrant oil of many plants (including geranium flowers). It is the E isomer of
Write bond-line formulas for each of the following naturally occurring compounds, clearly showing their stereochemistry. The worm in apples is the larval stage of the codling moth. The sex attractant of the male  moth is the 2Z,6E stereoisomer of the compound shown.
Draw (E)-5-methyl-5-heptene-1-yne.
The sex pheromone of the honeybee is the  E stereoisomer of the compound shown. Write a structural formula for this compound. 
A growth hormone from the cecropia moth has the structure shown. Express the stereochemistry of the double bonds according to the E – Z system. 
Which of the following are  E alkenes? (maximum of 2) Give the correct IUPAC name of the alkene D (from the answer options below).      
Assign the Cahn-Ingold-Prelog priorities directly on each structure and determine the configuration of the alkenes below.
Indicate if the following double bonds are  entgegen (E), zusammen (Z), or neither (Ne).
Which of the following is the correct configurational prefix for the triene below? List the configurations of the double bonds from left to right. (E,E,E) (Z,Z) (Z,E) (E,Z) (E,E)
Draw the geometric isomer, if any, of the following compounds.
Which structure shown below represents (Z)-4-bromo-4-cyclobutylbut-3-en-2-ol?
Give the IUPAC name for the following compound a) trans-3-chlorobut-2-en-1-ol b) cis-3-chlorobut-2-en-1-ol c) (E)-3-chlorobut-2-en-1-ol d) (Z)-3-chlorobut-2-en-1-ol
Draw the following molecule: (Z)-5-methylhex-2-ene
Draw the following molecule: (E)-4,5-dimethyloct-4-ene
Label the geometry of the following alkene derivative as either E or Z.
For the following molecules determine cis or trans?     a)    Cis; trans; trans; cisb)    Trans; trans; neither; neitherc)    Trans; trans; trans; cisd)    Trans; trans; neither; cis 
Draw the structure that corresponds to the following name:(3E,5Z,7Z)-1,3,5,7,10-undecapentaene
Provide a structural formula for the s-cis conformation of (E)-1,3-pentadiene. Note that any correct form of a structural formula is acceptable. Be sure to identify stereoisomers properly.  
Draw a representation of E-6-butyl-5-ethyl-4-decene
Designate the geometry of the following alkenyl bromide as either E or Z. 
Draw a representation of (Z)-3,4-dimethyl-3-decene
Which of the following alkenes exhibit E-Z isomerism? A) I and II B) I and III C) II and IV D) I, II, and III
Spell out the full name of the compound.
Name the following alkene. Be sure to use hyphens (-), not en-dashes (-). 
Be sure to answer all parts. Give the IUPAC name for the following compound.
Draw the molecule listed below.
The following compound would be named ____ -1,2-dimethylcyclopropane.a. neither cis nor transb. cisc. either cis or transd. trans 
Name the following compound. Do not include stereochemistry.
Draw the skeletal structure of (E)-5-phenylhex-2-en-2-ol. 
Assign the stereochemistry of the following alkene as E or Z
Provide an IUPAC name for each of the compounds shown. (Specify (E)/(Z) stereochemistry, if relevant, for straight chain alkenes only. Pay attention to commas, dashes, etc.) 
Name the following compound. Do not include stereochemistry.
Which of the following compounds exists as cis-trans isomers? (i) 1-pentene (ii) butane (iii) 2-methyl-1-butene (iv) 3-hexene (v) 2, 3-dimethyl-2-butene 
Decide for which of the following compounds cis-trans isomerism is possible and draw the trans isomer for that compound, clearly showing the geometry about the double bond.• 2-butene • 3-ethyl-2-methyl-2-pentene 
Which of the following is considered a Z-alkene?
Draw the structural formula of cis-1, 3-dimethylcyclohexane. Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. Show the appropriate stereochemistry by choosing the dashed or wedged buttons and then clicking a bond on the canvas.
What is the IUPAC name for the molecule shown here?
Click the "draw structure" button to activate the drawing utility. Draw the structure corresponding to the following IUPAC name. (E)-3,5,6-trimethyloct-2-ene
Name the following alkene. Be sure to indicate stereochemistry and use hyphens (-) not endashes (--).