UDEC 1134 (Chemistry Laboratory I)

Name: Ooi Jiaxin

ID: 1500257
Name of Partners: Tan Jia Ying, Rita Sharmila Dewi, Chung Li Ping
Practical Group: 5
Experiment No.: 6
Experiment Title: Preparation of Bis(acetylacetonato)copper(II)
Experiment Date: 21/01/2015
Submission Date: 04/02/2015
Lecturers Name: Dr. Sim Yoke Leng
D115M

Title: Preparation of Bis(acetylacetonato)copper(II)

Objective: To synthesise the bis(acetylacetonato)copper(II) complex
Introduction:
Transition elements can form coordination compounds. In coordination compounds, a
transition element acts as the central metal atom which shares and bonds to ligands which are
non-metallic ions or molecules via dative covalent bonds. In this phenomenon, the metal
atoms are actually the ones accepting or sharing donor pair electrons from the non-metallic
ions or molecules. The metal atoms act as Lewis acid (electron acceptor), whereas the nonmetallic ions or molecules act as Lewis base (electron donor). This occurs because transition
elements which are metals happen to have empty orbitals which are vacant to receive electron
pairs from ligands.
Coordination complexes happen to have physical and chemical properties which
differ from their respective metal ions or ligands which undergo bonded to form these
coordination compounds. One of the obvious differences that can be observed is the colour of
the coordination compounds. In this experiment, hexaaquacopper (II) ion, which is a complex
ion, is pale blue in colour; copper (II) hydroxide, which is a complex compound, is blue in
colour; whereas tetraaminediaqua copper (II) is dark blue in colour. The colour of the
coordination complexes depends solely on the portions of lights of the visible light is being
reflected, absorbed, or transmitted.
When the substance absorbs light, the electrons within the atoms of the substances are
excited and the five 3d orbitals split into 2 groups with different energy. The electrons that are
lying in the lower level of the 3d orbitals can absorb light to become excited and get
promoted to the higher level 3d orbitals. The colour of the compounds or substances shows
the light being reflected.
Apparatus: Beaker, glass rod, dropper, measuring cylinder, Bchner funnel, Bchner flask.
Materials: Copper(II) nitrate, ammonia, acetyl acetone.
Procedure:
6g of copper (II) nitrate (Cu(NO)3H2O) was dissolved in 60cm of distilled water.
The solution of 1:1 ammonia was slowly added with stirring until the precipitate first formed
has just redissolved. The solution was stirred continuously and 6 cm of acetyl acetone was
then added drop wise. The crude product was filtered off by using suction filtration. The
crude product was washed well with water and drained thoroughly. The percentage (%) yield
was calculated.

Results:
The mass of the empty beaker is 34.20g
The mass of the beaker with the product is 42.36g
The mass of the product is = 42.36g 34.20g = 8.16g
1 mole of Cu(NO) produced 1 mole of Cu(C5H7O2)2
Copper(II) nitrate

copper(II) acetylacetone

Let the number of moles of Cu(NO).3H2O be n1

Let the number of moles of Cu(C5H7O2)2 be n2
n1 = n2
mass of Cu(NO3)2.3H2O
relative molecular
mass of Cu(NO3)2.3H2O
6g
63.5+2(14+16(3))+
3(1(2)+16)
6g
241.5g mol-1

=
=

mass of Cu(C5H7O2)2 =
=

mass of Cu(C5H7O2)2
relative molecular
mass of Cu(C5H7O2)2
mass of Cu(C5H7O2)2
63.5+2(12(5)+1(7)
16(2))
mass of Cu(C5H7O2)2
261.5g mol-1

6g x 261.5 g mol-1
241.5g mol-1
6.497g theoretical mass of product

Given that percentage yield = actual mass of product

theoretical mass of
product
and the actual mass of product = 8.16g;
% yield = 8.16g
6.497g

100%

= 125.60%
Question:
1. Draw the structure of the complex.

100% ;

2. Describe the structure by mentioning the ligating atoms of the ligand and its
geometry.
The ligands for this complex are acetyl acetone. The two acetyl acetone(s) arranged
themselves neatly beside both sides of the copper (II) ion. With that, the two acetyl
acetone(s) can share their electrons with the copper (II) ion. The two oxygen atoms
each from the two acetyl acetone(s) donate their lone pairs of electrons to the copper
(II) ion which facilitates the pairs of electrons in its empty 3d orbital shells.
Discussion:
Note that copper is a transition element and it forms complex ions by acting as the
central metal atom which accepts pairs of electrons donated by ligands which are nonmetallic ions or molecules (Tan 2013) to form dative covalent bonds. Copper(II) nitrate is a
coordination compound that can still undergo certain reactions to form new coordination
compound. In this experiment, copper (II) acetylacetonato was synthesised from copper (II)
nitrate by exchanging the ligands through several steps.
A mass of approximately 6g of solid copper (II) nitrate was measured using the
weighing balance. When the copper (II) nitrate (Cu(NO 3)2.3H2O) was added into 60cm3 of
distilled water, copper (II) hexaaqua complex was formed as a pale blue solution.
Cu(NO ) (aq) + 3H2O (l) [Cu(H2O)6]2+ (aq) + 2NO3- (aq)

3 2
copper (II) nitrate

hexaaquacopper (II) complex

1:1 ammonia was then added into the hexaaquacopper (II) complex (pale blue
solution) to form copper (II) hydroxide solution. In this reaction, the insufficient amount of
ammonia was not able to displace the high concentration of water molecules which were
bonded to copper (II). Instead, the ammonia acted as a base which helped to pull hydrogen
ions off of the hexaaquacopper (II) complex (Clark 2003) to form copper (II) hydroxide
which was also a pale blue solution.
[Cu(H2O)6]2+ (aq) + NH3 (aq) [Cu(H2O)5(OH)]+ (aq) + NH4+ (aq)
As shown in the equation above, the equilibrium shifted to the right to produce more
complex ions (according to Le Chateliers principle). It was much easier for ammonia to react
against the hexaaqua ions than hydrogen ions as there are more hexaaqua ions present (Jim
Clark, 2003).
[Cu(H2O)5(OH)]+ (aq) + NH3 (aq) [Cu(H2O)4(OH)2] (s) + NH4+ (aq)
As more ammonia was added, precipitate was formed ([Cu(H 2O)4(OH)2]). The
equilibrium again shifted to the right as ammonia reacted with hydrogen ions or reacted with
the complex ([Cu(H2O)5(OH)]+).
The precipitate formed dissolved if excess ammonia was added. From here, we can
see that hexaaquacopper (II) complex is actually acidic as it dissociated to give away
hydrogen ions which might have formed ammonium ions with ammonia.
2+
2
6
hexaaquacopper (II) complex

[Cu(H O) ] (aq) + NH3 (aq) Cu(OH)2 (aq) + NH3 (aq) + 4H2O (l) + 2H+ (aq)
copper (II) hydroxide

or
[Cu(H2O)6] (aq) + NH3 (aq) Cu(OH)2 (aq) + NH4+ (aq) + 4H2O (l)
2+

hexaaquacopper (II) complex

copper (II) hydroxide

As more ammonia was added into the solution, there were enough amount of
ammonia to displace hydroxide ions to form tetraaminediaqua copper (II) complex. The
solution then turned dark blue.
[Cu(H2O)6]2+ (aq) + 4NH3 (aq) Cu[(NH3)4(H2O)2]2+ (aq) + 4H2O (l)
hexaaquacopper (II) complex

tetraaminediaqua copper (II) complex

When acetyl acetone was added into the solution, copper (II) acetylacetonato was
formed.
Cu[(NH3)4(H2O)2]2+ (aq) + 2C5H8O2 (aq) Cu(C5H7O2)2 (aq) + 4NH3 (aq) + 2H2O (l) + 2H+
acetylacetonato copper (II)

(aq)
The dry mass of the product needed to be obtained for the calculation of the
percentage yield. But first, the solution must be filtered while being washed with water (using
suction filtration). Hence, it was filtered using Bchner funnel and Bchner flask where
liquid was contained. As liquid was filtered off from the product, the product was collected
into a beaker and sent into the oven to dry. After drying, the product was weighed once again
and an actual mass of the product was obtained (8.16g).
In order to calculate the theoretical mass of the product, we assumed that 1 mole of
copper (II) nitrate reacted to produce 1 mole of acetylacetonato copper (II). A theoretical
mass of 6.497g was calculated, and the percentage yield of acetylacetonato copper (II) is
125.60%. This may be due to the product still having certain amount of fluid contained
within it, and hence the mass of the product was accumulated to 8.16g.
When handling hexaaqua copper (II) and copper (II) hydroxide solutions, direct
contact was avoided as they are acidic. When suction filtration was being conducted, the
layer of filter paper place inside the Bchner funnel was drenched with distilled water to
prevent the solution that is to be filtered from being filtered through the funnel into the
Bchner flask. Moreover, the filtered product was washed with water to remove impurities. It
should also be dried to obtain the accurate actual dry mass of the product itself, but for this
experiment we might not have completely dried the product in the oven even though it was in
powdery form.
Conclusion: The percentage yield of acetylacetonato copper (II) complex is 125.5%.
Reference:
1. Clark, 2003. Copper. [Online]. Available at:
http://www.chemguide.co.uk/inorganic/transition/copper.html [Accessed 3 February
2015]
2. Tan, L., L., H., 2013. Ace Ahead STPM Text Chemistry Second Term. Selangor Darul
Ehsan: Oxford Fajar.
3. Yip., 2013. Pre-U STPM Text Chemistry Term 2. Selangor Darul Ehsan: Pelangi.