CHEM 22552 – Organic Synthesis – Tutorial

1. Propose starting materials to prepare the following compounds by an aldol reaction.

CHO O

OH

2. Write the desired product/s for the following reaction.

O O

NaOEt A
i.
EtOH

O
NaOH B
O
ii.

O
LDA, -78 OC CH3CH2Br
C D
iii. THF EtOH

O O

NaOH E
+
iv.

v
+ F

O
3. Write the mechanisms for the following synthetic transformations.
O O
CH3

base
+ H3C
i.
O O

O
CH2CH3 CH2CH3

O O

ii.
CF3COOH O

O OH

iii. heat

4. How would you carry out the following transformations? Give reagents/conditions required. If
more than one step is involved give the product(s) of each step.
H C6H5
O

i.

O O O OH

ii. O

O O

iii.

HO
Br

Dr. Medha Gunaratna