Catherine Wrzesien

11-4-2015
Estimating Molecular Size and Bond Length
Introduction
Oleic acid stands when on the surface of water because of its opposite ends. One end of
the molecule is hydrophilic, attracts water, and the opposite end is hydrophobic, repels water.
The hydrophilic end of the molecule touches the surface of the water; but, the hydrophobic end
causes the standing by dramatically running away from the water. The standing of oleic acid
produces a flat cylinder. In this experiment we used two different models of oleic acid to predict
bond lengths. The first of these models is the stacked model in which the 18 carbons of the
molecules chain are bonded on top of each other in a straight line with a bond angle of 180.
The second type of model is the non-stacked model in which the 18 carbons of the chain are
bonded in a zig-zag line with a bond angle close to 109.
The goals of this experiment were to determine 3 main components of the cylinder
produced when oleic acid stands on the surface of watervolume, diameter, and height. These
3 components as well as the two different models previously mentioned were used to estimate
the C-C bond length of 1.305 and the C covalent radius of .6526 in the oleic acid molecule.
The model of a zig-zag line and bond angle close to 109 showed a more accurate view of the
molecule versus the not very accurate straight line model with a bond angle of 180.
Procedure
Volume of the Cylinder: Obtained, cleaned and dried graduated cylinder and added oleic acid
drop by drop until there was 2.0 mL of the solution counting each single drop. Repeated the
same process several times until a reproducible number of drops was reached. Used the
number of drops and the 0.2% by volume of oleic acid amount to calculate the volume of a
single drop of oleic acid. The solution is part ethanol and part oleic acid; so, the volume of only
the oleic acid in one drop of solution was calculated.
Diameter of the Cylinder: Filled a cleaned pie pan with water, sprinkled a relatively small amount
of talc on the surface of the water to be able to see any and all results. Added drop of oleic acid
solution and, with the cm side of a ruler, measured the diameter of the somewhat jagged circle
that formed from the talc being pushed away. Repeated this process 3 times or until
reproducible trials were achieved. Noted that the formula to be used later requires the radius,
not the diameter.
Height of the Cylinder: Calculated the height of the cylinder created by oleic acid on the surface
of water. Noted that this height is the length of one oleic acid molecule and that molecules
usually have lengths measured in not cm. Stated whether or not the number calculated was
reasonable or not.
Estimating C-C bond length and C covalent radius in oleic acid: Looked at the oleic acid
molecule three different ways and mathematically explored each.
1. Assumed that each of the 17 C-C bonds were stacked up in a straight line with bond
angles of 180. Drew a stick model of this idea and marked the height of the cylinder on

the drawing. Used the picture to calculate the C-C bond length in the oleic acid and the
covalent radius of carbon.
2. Noted that in reality the C-C-C bond angle is not 180, it is actually about 109. Used this
information to draw a stick model of the new angle idea and again marked the height of
the cylinder on the drawing. Used the drawing, the new bond angle, and the cylinder
height to calculate the C-C bond length and covalent radius of carbon. Noted if this
method estimated a longer or a shorter C-C bond versus the first method.
3. Noted that oleic acid has a cis double bond in the middle of the molecule that kinks or
bends the molecule shape. Copied the provided stick model that includes this kink/bend
and marked the height of the cylinder next to the drawing. Predicted (did not calculate!) if
the cis bond would make the bond length determined in the previous question too long
or too short.
Used the 92nd edition of CRC handbook of Chemistry and Physics to look up the actual length of
a C-C bond and then used this value to determine the actual covalent radius of carbon.
Compared the actual values to previously calculated values and noted which method (straight
line vs zig-zag) best predicted bond length and whether or not a bond length calculation
involving the cis double bond would improve or worsen the best previously determined
calculations.
Results
Volume of the Cylinder: Found the volume of the cylinder, created by oleic acid, with four
different trials (Table 1).
Table 1. Four trials of adding drop by drop of oleic acid solution to graduated cylinder (final
amount of 2 mL each trial) with the corresponding volume of one drop of solution and volume of
oleic acid per drop.

Trial 1
Trial 2
Trial 3
Trial 4
Average of all trials

Drops of oleic acid

solution in 2mL
123
92
62
64
85.25

Volume of one drop

of solution (mL)
0.0162
0.0217
0.0322
0.0312
0.0234

Volume of oleic acid

in one drop (mL)
3.24x10-5
4.34x10-5
6.44x10-5
6.24x10-5
4.68x10-5

The volume of a single drop of solution was determined by the following calculation: 2.0 mL/
85.25 (the average was used here as well as in other calculations to accurately represent the
entire experiments data). The volume of oleic acid in one drop was determined by the following
calculation: (0.2% pure oleic acid in solution/100) x 0.0234 mL.
Diameter of the Cylinder: After the diameter of the cylinder, produced by oleic acid in a pie pan
of water, was measured in 3 trials with a cm ruler it was noted that the formula to be used in the
next step required the radius. Due to the formula requiring the radius, the radius was calculated
based on the corresponding diameter for each trial (Table 2). The average of each radius was
used in the next calculations.
Height of the Cylinder: The height of the cylinder was calculated by mathematically putting the
previously calculated radius and volume into the provided volume equation. Because the height

of the cylinder corresponds to the C-C bond length and bond lengths are normally measured in
angstroms () each calculated cylinder height was converted into angstroms (Table 2).
Table 2. Three trials of measuring diameter of cylinder produced by oleic acid in pie pan of
water with the corresponding (previously calculated) volume of cylinder and newly calculated
height of cylinder.
Diameter of
cylinder (cm)
Trial 1

12

Radius of
cylinder
(cm)
6

Volume of
cylinder
(mL)
3.24x10-5

Trial 2

18.75

9.375

4.34x10-5

Trial 3

18

6.44x10-5

Average of
all trials

16.25

8.125

4.68x10-5

Calculated
height of
cylinder (cm)
2.866x10-7
(28.66 )
1.572x10-7
(15.72 )
2.532x10-7
(25.32 )
2.219x10-7
(22.19 )

Calculated
height of
cylinder (m)
2.866x10-8
1.572x10-8
2.532x10-8
2.219x10-8

The height of the cylinder was calculated by using the volume equation of V=r2h. An example
of this, using the average numbers, is: 4.68x10-5=(3.14)(8.125)2 h resulting in
h=4.68x10-5/(3.14)(8.125)2. The height of the entire oleic acid molecule is 22.19 .
Estimating C-C bond length and C covalent radius in oleic acid. It was first assumed that the 17
C-C bonds in oleic acid are stacked up in a straight line (Figure 1). The C-C bond angle of this
model was 180 and the C covalent radius was 6.525 (Table 3). The C-C bond length in the
180 model was calculated by the following process: 22.19 /17 because there were 17 straight
line bonds. Secondly, it was understood that the 17 C-C bonds in oleic acid are actually not
stacked in a straight line; but, in a zig-zag manner (Figure 2). The C-C bond angle in this real
life model was 109 and the C covalent radius was .799 (Table 3). The C-C bond length in the
109 model was calculated with the following trigonometric equation: 1.305 /sin(54.75). This
equation was used because 1.305 was opposite the known C-C bond angle and 54.75 was
used in the sin formula because it was half of the 109 C-C bond angle.
Table 3. C-C bond length and C covalent radius of both the 180 model (straight line) and 109
model (zig-zag).

180 model
(straight line)
109 model (zigzag)

C-C bond length

(m)
1.305x10-8

C-C bond length

()
1.305

Covalent Radius
of C (m)
6.525x10-8

Covalent Radius
of C ()
6.525

1.598x10-8

1.598

.799x10-8

.799

C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
Figure 1. Straight line C-C bonds with 180.
Molecule length is 22.19 .
C-C bond length is 1.305 .

Figure 2. Zig-Zag C-C bonds with 109

Molecule length is 22.19 .
C-C bond length is 1.598 .

Discussion
The C-C bond length calculated using the 180 model of 1.305 was shorter than the CC bond length calculated using the 109 which was 1.598 . The two calculated bond lengths
were different even then from the C-C bond length found in the CRC hand book which was
1.526 . The 109 bond angle method predicted a bond angle closest to the CRC hand books
C-C angle. We expected the 109 method to be a better predictor because that method uses the
actual shape and proper organization of the C-C bonds in a zig-zag manner rather than the
straight line shape. These final results are reliable based on the cylinder size measured at the
beginning because the circle made by the oleic acid was exceptionally large as it was supposed
to be. They are also reliable because two reproducible trials were completed with circle
measurements of within 1cm of each other.

Oleic acids cis double bond between carbon-9 and carbon-10 puts a bend in the
molecule, making the entire molecule look similar to an L with a drooping horizontal line. If the
bond length was calculated with this bend taken into consideration the bond length would
change. The end bond length would be longer than predicted if the cis double bond was in the
calculation. The bond length would be longer because the bend in the molecule adds length.
The stearic acid molecule has a similar structure to the oleic acid molecule in that
instead of a double bond in the middle it has a single bond and is a straight molecule. Because
the stearic acid molecule has no bend in the middle it can better arrange itself around other
molecules. The oleic acid molecule will be father away from another oleic acid molecule and will
therefore be liquid. The stearic acid molecule will be able to get close to another stearic acid
molecule and will therefore be solid.
Conclusion
The height of the oleic acid molecule was 22.19 long. The C-C bond length in the 180
model was 1.305 ; but, the C-C bond length in the 109 model was 1.598 . The 109 model
produced a more accurate C-C bond length because it was closer to the actual bond length
found in the CRC handbook.