Chapter 2 Exercise

From the above reaction:

1. What is the overall type of reaction?
2. What type of intermediate is formed?
3. Draw the electron movement for the second step.
4. If the reaction gives off heat, draw the energy diagram of the reaction.

Answers

1. This is a substitution reaction. In this type of reaction, an atom or group of atoms

is replaced by another atom or group of atoms in a molecule. In addition reactions,
double bonds or triple bonds are usually lost and all parts of the adding reagent
appear in the product, Usually, two molecules become one. For elimination
reactions, double bonds or triple bonds are formed by losing atoms or groups of
atoms. Another type of reaction that is not mentioned in the lecture video is
rearrangement reactions. An example of such reaction is given below. In the said
type of reaction, there is reorganization of the molecule’s constituent parts. No
atoms are lost, gained, nor substituted. This usually involves movements of double
bonds or alkyl groups.

2. The intermediate formed is a carbocation.

3.
+

Remember that the flow of the electron should always be from the electron-rich
to the electron-poor region as indicated by the arrow tail and head.
 4.

B
D
Energy

A C

Reaction Time

A is the initial reactant, 2-bromobutane. As the bromine atom breaks its bond with
carbon, the transition state B is formed. The difference in the energy of A and B
corresponds to the activation energy needed to form (step 1) structure C, which is a
carbocation intermediate. This carbocation C will react and form bond with Cl - to form the
transition state D. The difference between C and D relates to the activation energy needed
to form product E from C and Cl- (2nd step) to form product E, 2-chlorobutane.
Step 1 having a higher activation energy than step 2 implies that the first step is
the rate-determining step or the slowest step.
Comparing the energy of reactant A and product E (i.e. A has a higher energy than
E) means that the reaction gives off energy, and thus is exothermic. Some of the energies
from A were given off as heat.