Functional Classes II, Reactions - Organic Chemistry Concepts: An EFL Approach - page 135

F The first step of the mechanism is the protonation of the alcohol hydroxyl group.
Depending on the particular alcohol R-group, either an S N 1 or S N 2 type of conversion
follows.

R R Cl

S N 1

H

C l

R OH R OH 2

S N 2

R Cl

C l

The use of an acid catalyst is often used to improve the leaving group of certain strong
conjugate bases (nucleophiles).

Q 7.2 Complete the following nucleophilic substitution reaction equations
by giving either the product or an appropriate reagent. In each case, give
the functional class of both substrate and product.

Q 7.3 The S N 2 reaction of 1-bromobutane with NaOH occurs readily. What
happens to the rate of this reaction if

(a) the concentration of NaOH is doubled.

(b) the concentrations of both NaOH and 1-bromobutane are doubled.

(c) the volume of the reaction solution is doubled.