Here is some discussion, to aim you a little.

1. a. The simplest 5-C alcohol might be 1-pentanol. That is a primary alcohol, but its formula is C₅H₁₂O. So it has too many hydrogens. To remove two H, you need to include either one double bond or one ring.

Putting a double bond right next to the -OH group is not good; this gives an ene-ol (enol), which is not stable (Ouellette 2/e Sect 4.10).

2. Since all the compounds being considered are isomers, mass is not an issue. Thus the main consideration is the general behavior of each functional group.

3. a. "Reacts with sodium" means it is an alcohol. "Not with KMnO₄" tells you that it does not have a C=C double bond, nor any other group that is easily oxidized, such as primary or secondary alcohol. Thus you know that it is an alcohol, but not a primary or secondary alcohol. Thus you conclude???

You also know that it is short 2 H of the maximum, but does not have any C=C double bonds. So you conclude?

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Last update: August 16, 2011