Problems 133

When you have read through all the different types of reaction mechanism, practise drawing them
out with and without the help of the book. Complete the exercises at the end of the chapter and then
try to devise mechanisms for other reactions that you may know. You now have the tools to draw out
in the universal pictorial language of organic chemists virtually all the mechanisms for the reactions
you will meet in this book and more besides!
Problems
1. Each of these molecules is electrophilic. Identify the elec- 3. Complete these mechanisms by drawing the structure of the
trophilic atom and draw a mechanism for reaction with a general- products in each case.
ized nucleophile Nu–, giving the product in each case.
O O O (a) H ?
O HO O Cl
O
H
Br
H (b) NH2 ?
S
Cl Cl Me Cl MeO OMe
4. Each of these electrophiles could react with a nucleophile at (at
2. Each of these molecules is nucleophilic. Identify the elec- least) two different atoms. Identify these atoms and draw a mech-
trophilic atom and draw a mechanism for reaction with a general- anism for each reaction together with the products from each.
ized electrophile E+, giving the product in each case.
H H H Ph Ph
H H N HO P OH
R Al H2N NH2 Ph
MeO OMe O
Me Me
O
R OMe NH
P
S S MeO OMe Me Me

5. Put in the arrows on these structures (which have been drawn with all the atoms in the right places!) to give the products shown.
O OH O O H O

(a) H + H OH + H

O O
(b)

Br

6. Draw mechanisms for these reactions. The starting materials 7. Draw a mechanism for this reaction.
have not necessarily been drawn in a helpful way. PhCHBr.CHBr.CO2H + NaHCO3 PhCH=CHBr
NaOH
(a) Br OH Hints. First draw good diagrams of the reagents. NaHCO3 is a salt
H2O and a weak base—strong enough only to remove which proton?
Then work out which bonds are formed and which broken, decide
EtCH2SH
Br S whether to push or pull, and draw the arrows. What are the other
(b)
NaOH, H2O products?
O OH
CH3 HBr
(c)