5 Reactions of Alkanes, Alkenes, and Alkynes

5.1 Introduction

In the preceding four chapters you have been introduced to a wide range of basic prin-
ciples that govern the structure, shape, and reactivity of organic molecules. We are fi-
nally ready to start applying these principles to actual molecules and their reactions.
In this chapter, we will look at some reactions of hydrocarbons, and particular atten-
tion will be paid to alkenes. Some of the reactions we will see do not fit the general
mechanistic types we will be developing and therefore must be learned separately.
However, most will be considered from the viewpoint of what is actually happening
as the molecules react: i.e., the mechanism.

5.2 Reactions of Alkanes

This section will be quite brief simply because, on the usual scale of reactivities, alka-
nes (saturated hydrocarbons) are quite unreactive. Furthermore, those reactions they
do undergo do not fit the type of mechanistic pathways we will be considering.

5.2.1 Oxidation

The most general reaction undergone by alkanes is combustion: i.e., their oxidation
in air. For example
CH4 + 2O2 󳨀→ CO2 + 2H2 O + heat

This, of course is the reaction that heats houses and powers internal combustion en-
gines. It is also useful for determining the molecular formula of organic molecules (see
Problem 2.4).

The ultimate goal of any organic chemistry course is to be able to predict, from a knowledge of
mechanism and/or by analogy with similar molecules, how a particular molecule will react under
given conditions. It is strongly suggested that you start a list of the reactions we have discussed
and keep it up-to-date, lecture by lecture. This will greatly simplify review. It is also important to
realize that the reactions must be learned frontwards and backwards. That is – we will see a reac-
tion where A gives B under certain conditions. You should remember this in terms of how A reacts
and also how to prepare B.

https://doi.org/10.1515/9783110565140-005