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Synth Cis and Trans Cu (Ii) Aen Student

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12 views2 pages

Synth Cis and Trans Cu (Ii) Aen Student

practical

Uploaded by

laxeg75876
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Synthesis of cis- and trans-copper(II) aminoethanoate

Student worksheet

Soluble copper(II) salts dissolve in water to give a solution of


Glycine hexaaquacopper(II) ions, [Cu(H2O)6]2+.
(aminoethanoic
Glycine (systematic name: aminoethanoic acid) has the
acid)
molecular formula C2H5O2 and structural formula H2CH2COO.
When dissolved in an alkali such as sodium hydroxide, the
Glycinate ion carboxylic acid group ionises to give an ion with a single
(aminoethanoate negative charge. It is called a glycinate ion (systematic name:
ion aminoethanoate, H2CH2COO−).

ic acid)
The copper(II) complex of glycine can be made by adding a hot aqueous glycine solution to a hot
solution of copper ethanoate in a water-ethanol mixture.

Equipment and materials for both preparations


 Hot water bath or electric heating  50 cm3 round-bottom flask (Quickfit)
mantle
 Condenser (Quickfit) to fit the 50 cm3 round-
3
 25 cm measuring cylinder bottom flask
 2 x 100 cm3 conical flasks  Bunsen Burner, tripod and gauze
 2 x 250 cm3 conical flasks  Sample tube (2)
 Water bath  Ethanol
 −10 – 110 °C thermometer  Copper(II) ethanoate-1-water
 Filter funnel and fluted filter paper  Glycine
 Watch glass (2)  Ice

Synthesis of cis-Cu(H2CH2COO)2.H2O
Method
Care: Wear eye protection. Copper(II) ethanoate-1-water is harmful and an irritant. Ethanol is
flammable. Work away from naked flames. As industrial denatured alcohol or ethanol formulated
with methanol (IDA/IMS – industrial methylated spirits) is being used, there may be toxicity issues
from methanol (or other adulterants) so work in a well-ventilated lab.
1. Using a measuring cylinder, measure out 25 cm3 of ethanol into a 100 cm3 conical flask and
place the flask in a hot water bath at 65 °C.
2. Using a measuring cylinder, measure 25 cm3 of water into a 250 cm3 conical flask. Weigh out
2.0 g (0.01 mol) of copper(II) ethanoate-1-water and add to the flask. Place the flask in the
water bath and stir the mixture until the solid dissolves. When the solution reaches 65 °C pour
the warm ethanol into the copper(II) ethanoate solution.
3. Using a measuring cylinder, measure 25 cm3 of water into a 100 cm3 conical flask. Weigh out
1.5 g (0.02 mol) of glycine and add to the flask. Place the flask in the water bath. Stir the
mixture until the solid dissolves. When the solution reaches 65 °C pour it into the flask
containing the copper(II) ethanoate solution.

1
4. Cool the mixture in an ice bath. Light blue needles should crystallise. Filter the cold mixture
through a fluted filter paper. Collect the filtrate in clean 250 cm3 conical flask and keep it for the
synthesis of trans-Cu(H2NCH2COO)2.H2O.
5. Open up the filter paper and lay it on a watch glass. Cover the crystals with a piece of clean
filter paper and leave it to dry in a fume cupboard at room temperature.
6. Label a sample tube with the name of the product, your name and the date. Weigh the labelled
sample tube and record its mass.
7. Scrape the dried crystals into the weighed sample tube. Weigh the tube again. Record its
mass.

Calculations
Calculate the theoretical yield and the percentage yield.

Synthesis of trans-Cu(H2CH2COO)2.H2O
Method
1. Weigh about 1.5 g of cis-Cu(H2NCH2COO)2.H2O and 1 g of glycine into a 50 cm3 round-bottom
flask.
2. Use a measuring cylinder to pour 10 cm3 of the filtrate from the synthesis of cis-
Cu(H2NCH2COO)2.H2O into the flask, fit a condenser and reflux the mixture for one hour (use a
hot water bath or electric heating mantle).
3. Filter the hot mixture through a fluted filter paper to obtain blue-violet platelets of trans-
Cu(H2NCH2COO)2.H2O.
Note that if the mixture all dissolves during the reflux, then the cis-product will re-precipitate not
the trans isomer.
4. Open up the filter paper and lay it on a watch glass. Cover the crystals with a piece of clean
filter paper and leave it to dry in a fume cupboard at room temperature.
5. Label a sample tube with the name of the product, your name and the date.
6. Scrape the dried crystals into the weighed sample tube.
It is not possible to get a meaningful value for the percentage yield as the exact quantity of cis-
Cu(H2NCH2COO)2.H2O is not known.

Finally
Why does the structure change from the cis isomer to the trans isomer? The initial reaction mixture
contains both cis and trans isomers in equilibrium, but the cis isomer crystallises faster. However
the trans isomer is thermodynamically more stable and less soluble, so on continued heating, the
only product is the trans isomer.
 Make molecular models and draw structures for the two geometrical isomers of copper(I)
aminoethanoate.
 Do you think there are any benefits of using one isomer rather than the other as a source of the
micronutrient copper?

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