Experiment 5

86

Experiment 5:

Winter 2013

Synthesis of cis- and trans- bis Glycinato

Copper(II) Monohydrates

Introduction
In this experiment you will prepare a pair of geometric isomers of a coordination complex. The glycinate ion, NH2CH2CO2-, is a bidentate ligand which can form coordinate bonds to
metal ions via both nitrogen and oxygen atoms. Copper forms a square planar complex with the
glycinate ion in which the central copper ion is coordinated to two glycinate ions. When prepared at room temperature, the kinetically stable cis isomer forms. The same reaction done under reflux conditions will initially form the cis isomer, but on heating the cis compound is converted to the thermodynamically more stable trans isomer.

A.

Preparation of trans-Cu(NH2CH2CO2)2.H2O

Chemicals required
Copper (II) acetate monohydrate

2.0 g

Glycine

1.5 g

Equipment required
a) ring stand

b) ring clamp

e) 100 mL round bottom flask

c) heating mantle
f) paddle clamp

h) thin-walled rubber tubing, two pieces

j) stirring bar
Note:

d) Variac
g) condenser

i) adjustable clamp

k) magnetic stirrer

This preparation is done under reflux conditions using a heating mantle. You will be
shown how to set up the necessary apparatus. This preparation (trans isomer) in-

volves refluxing for 1 hour. During this time period, you should proceed with the preparation of
cis-Cu(NH2CH2CO2)2.H2O (part B of this experiment).
Procedure
Dissolve the glycine in 25 mL of hot deionized water in a 150 mL or 250 mL beaker.
Now place the copper (II) acetate in a 100 mL round bottom flask and to it add 25 mL of hot deionized water. Place a stir bar in the flask and ensure that the copper (II) acetate is completely
dissolved. Add 25 mL of 95% ethanol to the hot copper(II) solution. Add the hot (~70 C) glycine solution to the hot copper solution. Equip the flask with a reflux condenser and heat the
mixture using a heating mantle controlled by a Variac. The mixture should be continuously and
vigorously stirred using a stirring bar and a magnetic stirrer while refluxing for one hour. After
refluxing is complete, collect the product from the hot solution using suction filtration with a

Experiment 5
A.

87

Winter 2013

Preparation of trans-Cu(NH2CH2CO2)2.H2O

Procedure (continued)
Buchner funnel. Spread the partially dry solid onto a watch glass and allow it to dry over the
week in your locker. Determine a mass yield and calculate a percent yield for this product.
Submit your product with your lab report.

B.

Preparation of cis-Cu(NH2CH2CO2)2.H2O

Chemicals required
Copper (II) acetate monohydrate

2.0 g

Glycine

1.5 g

Procedure
Dissolve the glycine in 25 mL of hot deionized water in a beaker. Now dissolve the copper (II) acetate in 25 mL of hot deionized water in a second beaker and to it add 25 mL of 95%
ethanol. Add the hot (~70 C) glycine solution to the hot copper solution. Allow the resulting
solution to cool for a few minutes and then cool it in an ice bath. Collect the precipitate using
suction filtration with a Buchner funnel. Wash the crystals once with a small volume of cold 95%
ethanol and allow the product to air dry on suction. Spread the relatively dry product out on a
watch glass and allow it to dry in your locker over the week. Record the yield of dry product and
store it in a labelled sample vial. Calculate a percent yield for this product and submit it for
grading.

C.

Microscope Use
View both of the synthesized products using a microscope. Draw a sketch of each

product and record a description of what you see using the microscope.

Questions
1.

The two products synthesized in this experiment are a pair of cis and trans isomers. Provide a definition of a physical property. List three physical properties
that should differ for these two compounds

2.

Draw diagrams of the structures of the two isomers showing three dimensions.
Show all of the atoms in each structure.

Experiment 5

88

Winter 2013

References
N.N. Greenwood and A. Earnshaw, Chemistry of the Elements.
C.E. Housecroft and A.G. Sharpe, Inorganic Chemistry, second edition.
P. O'Brien. J. Chem. Ed. 59 (12), 10521053, 1982.
R.H. Petrucci, W.S. Harwood et al., General Chemistry: Principles and Modern
Applications, 9th edition.
R.H. Petrucci, F.G Herring et al., General Chemistry: Principles and Modern
Applications, tenth edition.
G. Rayner-Canham and T. Overton. Descriptive Inorganic Chemistry, third edition.
N.J. Tro, Principles of Chemistry A Molecular Approach.