You are on page 1of 4

Once you get a handle on oxidations and reductions, you might start to notice that with

some molecules these reactions can proceed in sequences.


For example, if you start with an alkane with a CH3 group,

the alkane can be oxidized to a primary alcohol.


The alcohol can be oxidized to an aldehyde
The aldehyde can be oxidized to a carboxylic acid.
(The reverse reactions would all be reductions, of course)
Each of these reactions involves the gradual increase in oxidation state at carbon. If you
arrange these reactions with increasing oxidation state on the y axis, you get patterns
which are often called oxidation ladders, and they are extremely useful way of
organizing reactions. (We could do the reverse reactions and call it a reduction ladder
for some reason the name oxidation ladder has stuck).
Thats why we often say that we oxidize the alcohol up to an aldehyde, and reduce an
aldehyde down to an alcohol.

Similarly, if you start with an alkane with a secondary carbon:

the secondary carbon can be oxidized to a secondary alcohol


the secondary alcohol can be oxidized to a ketone
The ketone can even be oxidized to an ester
Heres the oxidation ladder for that sequence.

Finally, you can also think about oxidation ladders involving double bonds.

Alkanes can be oxidized to alkenes.


Alkenes can be oxidized to alkynes
Some alkynes can even be oxidized further into ynols, an interesting but
somewhat exotic species I wont get into.
Its also a useful concept for organizing reactions that dont involve climbing or
descending the oxidation ladder. For instance, alkenes can be converted into either
primary or secondary alcohols, depending on the choice of reagent and either of these
can be converted back into alkenes. Similarly, alkynes can be converted into either
aldehydes or ketones, depending on the choice of reagent, and neither of these
transformations are considered to be oxidations nor reductions.
In the big picture, you can think of two types of reactions: vertical reactions, in which
the oxidation state of a molecule is changed, and horizontal reactions, in which
functional groups are interconverted.

One final note. In general, oxidation is a thermodynamically more favorable process than
reduction (due to the higher bond strength of C-O vs. C-H). At this very second, sugars
(alcohols) in your body are ascending the oxidation ladder to become carbon dioxide,
releasing energy in the process. Conversely, photosynthetic bacteria and plants are
employing sunlight (an external source of energy) to assist in the conversion of carbon
dioxide down the oxidation ladder to become aldehydes, alcohols, and alkanes.