13. Alkenes, Alkynes, and Aromatic Compounds

Which of the following compounds are capable of cis–trans isomerism?

a.

b.

c.

Why do you suppose small-ring cycloalkenes like cyclohexene do not exist as cis–trans isomers, whereas large ring cycloalkenes like cyclodecene do show isomerism?

Name all unbranched ether and alcohol isomers with formula C₅H₁₂O and write their structural formulas.

Identify the compounds in each of the following pairs as structural isomers or not structural isomers:

b.

Indicate whether each of the following pairs represent structural isomers or the same molecule:

b.

Identify the following pairs of structures as structural isomers, cis–trans isomers, or the same molecule:

a.

Draw the condensed structural formulas for all the possible haloalkane isomers that have four carbon atoms and a bromine.

Indicate whether each of the following pairs represent structural isomers or the same molecule:

a.

What is the difference between a conformational isomer of a compound and a structural isomer of the same compound?

Determine the relationship between each of the pairs of the following compounds. Are they structural isomers (different molecules), conformational isomers (the same molecule), or not related?

(b)

Determine the relationship between each of the pairs of the following compounds. Are they structural isomers (different molecules), conformational isomers (the same molecule), or not related?

(a)

Determine the relationship between each of the pairs of the following compounds. Are they structural isomers (different molecules), conformational isomers (the same molecule), or not related?

(d)

Determine if each of the following cycloalkanes or alkenes can exist as cis–trans stereoisomers. For those that can, draw the two isomers. Label each of the isomers you drew as the cis stereoisomer or the trans stereoisomer.

(b) CH₃CH₂CH₂CH₂CH=CH₂

Alkanes are also referred to as saturated hydrocarbons. Explain the meaning of the term hydrocarbon. Why are alkanes called saturated hydrocarbons?

Draw skeletal structures for each of the following molecules:

(b) cis-1-chloro-3-methylcyclohexane