Question 26.10: Determining the Degree of Unsaturation and Suggesting Possib......
Determining the Degree of Unsaturation and Suggesting Possible Structures for a Molecule
What different types of compounds are possible for a compound with the molecular formula C_{6}H_{10}O?
Analyze
We need to establish the degree of unsaturation in the molecule and then construct one example of each type of molecule that can be formed.
Solve
As we described above, we can ignore the oxygen atom in determining the degree of unsaturation. The maximum number of hydrogen atoms is 2 × 6 + 2 = 14. The molecular formula has only 10 hydrogen atoms, so we know the degree of unsaturation is two. What types of molecules can be formed? We might start by considering dienes (alkenes with two double bonds) with either an alcohol or an ether functional group.
Alternatively, we can have a cyclic alkane with a carbonyl group or a cyclic alkene with an alcohol functional group. Two possible structures are shown here.
Two other possibilities are a ketone with an alkene side chain or an aldehyde with an alkene side chain. Two possible structures are shown here.
Assess
We have provided an example of an ether (with two degrees of unsaturation in the alkane chain), an aldehyde (with one degree of unsaturation in a side chain), a ketone, and some alcohols. This list is not exhaustive and you should be able to find other isomers.