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Experiment 9: Synthesis of cis- and trans- bis Glycinato Copper(II) Monohydrates

Page 1

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 glycinato ion in which the central copper ion is coordinated to two glycinato 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

Glycine

Note:

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) involves 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. 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 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.

Page 2

B.    Preparation of cis-Cu(NH2CH2CO2)2·H2O

Chemicals required

Copper (II) acetate monohydrate

Glycine

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 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.    Melting Points and Microscope Use

i) Melting Points

Determine the melting points of both synthesized products using an Optimelt melting point apparatus. Consult with a lab instructor to determine the procedure to use to determine the melting points. Measure and record the melting points.

ii) Microscope

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. List three physical properties that should differ for these two compounds using evidence from the lab.

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

Page 3

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), 1052–1053, 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.

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What the Untitled Document Is and when it’s used

The Untitled Document is a general-purpose written agreement template used to record commitments, terms, or disclosures between parties in the United States. It can function as a contract skeleton, cover letter, or form-based record where signatures, dates, and key fields are required to establish rights and obligations. When completed with the required information and proper signatures, it creates an enforceable record under U.S. electronic-signature law provided statutory exceptions do not apply and retention and authentication requirements are met.

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Frequently asked questions and quick resolutions

Answers to common questions about completing, signing, and storing the Untitled Document in U.S. contexts.


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