2

Question 1 (6 marks)
a) 4-Pyrone (below) is protonated by acid to give a stable cationic product. Propose a structure for
this product and explain why it is relatively stable.
O
O
H
+


b) Draw the product of the reaction in (ii).
(i)




(ii)





c) Why does reaction (ii) proceed but not reaction (i)?




OH
H
+
no reaction
H
+
faster reaction
OH
3

Question 2 (7 marks)
Write the reagents required to perform the following transformations in the boxes below. There may
be more than one reaction in each box. Where necessary, separate these with reaction numbers 1,2,
etc. Pay attention to the direction of the reaction arrows!
a)
OH
H
O
H
O
OH
Cl
O
O

b)
Cl
O
O
O
O
O
O
O O
CH
3
CH
3

4

Question 3 (8 marks)
a) Label the following reactions by writing (A) reduction (B) oxidation or (C) neither above the
reaction arrows.
H
H
H H



O
O
OH
2



H CH
3
O
H CH
3
O O H
3
C CH
3




b) Label the following molecules as (A) aromatic (B) anti-aromatic or (C) non-aromatic.

O
O
N
H
H

5

Question 4 (10 marks)

Predict the major product(s) of the following reactions.
a)






b)



c)




d)



e)

O
O
1. LiAlH
4
2. H
+
workup
O
O
O
H
2
O
H Cl
O
1. 2 CH
3
CH
2
MgBr
2. H
+
workup
OCH
2
CH
3
O
O
2
N
H
N
+
NH
2
O
O
H
2
O, H
+
6

Question 5 (8 marks)
a) Using methylbromide as your only other carbon source, show how you would carry out the
following multi-step synthesis. Show all reagents and products for each step. You DO NOT need to
show a detailed mechanism or stereochemistry.

H
3
C
OH
H
3
C CH
3
CH
3
Br
C C H
3
C H



















7

Question 6 (11 marks)
Propose a detailed step-by-step mechanism for the following reaction. Draw the hemi-acetal
intermediate in the box below, and show all electron movement arrows, formal charges, and
intermediates.
O
H
2
O, H
+
HO
H
O
H
2
O, H
+