School of Physical & Mathematical Sciences

Division of Chemistry & Biological Chemistry

H3 Organic Synthesis and Mechanism - Tutorial 8

Carbonyl Compounds, Carboxylic Acids and Derivatives

1) Identify the structures or the reagents A to N for the following reaction

scheme.
I

A C D F H
B E G NH2
Br CO2H
J K

L O N O
H M

OH
O
HO

2) What you had learnt is applicable in many synthetic sequences for the
syntheses of complex natural products. Below is taken from the synthesis
of the antibiotic Monensin by Still et al. (J. Am. Chem. Soc., 1980, 102,
2117-2121). Identify the structures or the reagents O to Q.

Me Me
O
1. LiAlH4 (excess) /H+ PCC
HO O P O
O
O 2. NH4Cl (aq) H
O O
H

Me Q
HO
Me
O O Me
Me O Me H Et O H Me
H Me O
Me
HO O O H
OMe
Me
Me HO2C
CO2Na HO Me

(+)-monensin sodium salt

School of Physical & Mathematical Sciences
Division of Chemistry & Biological Chemistry

3) The following organic compounds are available in your laboratory:

HO Br CH3Br

HC CH
Using the above compounds (not all of them may be useful), and any other
organic or inorganic reagents, propose a synthetic route each for the
following compounds:

NH2

O O

OH

O
OH

HO

4) Propose mechanisms for the following reactions, showing movement of electrons

using curved arrows and show all intermediates if necessary.

(a) MgBr
1. BrMg
O OH
O 2. H3O+
HO
O
(b) NH2
O
HN
OH + O + 2 HO
O O

(c)
H+
+
OH O O
O