Bond Rotation
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C-C Bond Rotation
Dr. Edmund Nip
Chem 301-61
Hampton University
October 2, 2018
Hannah Collins
Lindsey Johnson Ashley Manuel
Abstract In this experiment the bond rotation between carbon 2 and carbon 3 was observed. The bond was
rotated every 10 degrees from 0 until 360 degrees was reached. Chem draw was used to draw structures and rotate the bond angles to find the dihedral angle and the corresponding energy of the molecule every 10 degrees until 360 degrees was reaches. This was the purpose of the experiment. Background
A Newman projection is a drawing convention. The bond looks down a specific bond and the bond being looked down was between C2 and C3. Most rotated molecules are rotated 60 degrees
all the way until 360 degrees but in this lab rotation was done every 10 degrees. Bond rotation strains are caused by the electrons in between different groups. Torsional strain is when the repulsion caused by the electrons in between different groups when they pass b each other. When a molecule is rotated around the sigma bond, there is going to be different levels of torsional strains that can change the placements of the substituents. This is how we come up with different conformations of molecules like staggered or eclipsed and the different energy levels and stability levels as well. The reagents that are being used within the system to do bond rotations is butane, 2-methylbutane, and 2,3-dimethylbutane. When you move
the bonds around the different arrangements are a result of the sigma bond rotation that is known
as conformations. This strain is due to electron repulsion or when it is not in its ideal geometry.
Purpose
To draw structures using ChemMagic and rotate the structures to find the cinedral angle and the corresponding energy of the molecules every 10 degrees until 360 degrees was reached.
Table of Reagents Compound molecular weight amount used B.P/M.P
density
Butane 58.12 g/mol
N/A
30.2
0
F/-220
0
F 2.48kg/m
3
2-methyllbutane 72.15g/mol
N/A
27.8
0
C/-160
0
C 616 kg/m
3
2,3-dimethylbutane 86.17g/mol N/A
58.3
0
C/-124
0
C 660 kg/m
3
Hazards Butane : extremely flammable and explosive
2-methylbutane: extremely flammable liquid and vapor
2 3-dimethylbutane: highly flammable liquid and vapor
Procedure The ChemMagic site was opened on a web browser. The “draw” button was selected under the “load Models” section. The skeletal structure of the compound, butane, was drawn. The “load models” button was clicked on once the structure was complete. The 3D model of the structure appeared and then the structure was optimized by selecting the “optimize” button under
the “Other Model Actions” section. The optimization number appeared at the top of the page. Next, “torsion” was clicked on under the “Other Model Actions” section. Four connected carbon atoms on the structure were clicked on an angle close to 180
0
appeared between the atoms. “Rotate bond” was selected and then the C2-C3 bond was clicked on. Then, the carbons were circled in red. The bond angle was rotated as close as possible to 0
0
. Under the “Other Model Actions” section “energy” was selected. The energy in KJ appeared on the screen. The bond angle and energy was recorded. “Rotate bond” was clicked on angle and the angle was rotated 10
0
. The energy button was selected and the bond angle and energy were recorded again. This part was repeated until the bond rotated 360
0
. This entire procedure was done for 2-methylbutane
and 2,3-dimethylbutane as well, making sure the center C-C bond was selected and rotated.
Data Butane bond angle
energy
0.2
26.375
10.2
23.22
20
16.12
30
7.933
40
0.468
50
-6.218
60
-11.774
70
-14.739
80
-14.414
90
-11.51
100
-7.783
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110
-4.86
120
-3.806
130
-4.988
140
-8.135
150
-12.45
160
-16.796
170
-19.996
180
-21.168
190
-19.984
200
-16.775
210
-12.425
220
-8.115
230
-4.976
240
-3.806
250
-4.871
260
-7.797
270
-11.525
280
-14.412
290
-14.742
300
-11.741
310
-6.217
320
0.47
330
7.937
340
16.124
350
23.363
360
26.376
0
50
100
150
200
250
300
350
400
-30
-20
-10
0
10
20
30
Bond rotation C-C bonds (butane)
Bond Angle
Energy level (kJ/mol)
2-methylbutane bond angle
energy
0.4
36.293
10.4
33.659
20.4
27.458
30.4
20.088
40.4
13.529
50.4
8.962
60.4
7.183
70.4
8.414
80.8
12.107
90.8
16.764
100.6
21.444
110.5
25.212
120.9
26.758
130.9
24.867
140.9
20.06
150.3
14.282
160.3
8.427
170.3
4.035
180
1.885
190
2.266
200.6
4.907
210.7
9.252
220.7
14.023
230.9
17.05
240.7
19.427
250.7
18.607
260
15.331
270.6
11.299
280.6
7.374
290.8
5.57
300.8
6.919
310.8
11.07
320.8
16.575
330.9
36.293
340.8
33.659
350.8
27.458
360.8
20.088
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2,3-dimethylbutane
0.6
71.608
10.7
67.808
20.6
59.638
30.6
50.416
40.7
42.303
50.7
36.258
60.7
33.043
70.6
33.497
80.7
37.327
90.7
43.043
100.2
49.063
110.6
54.55
120.8
56.56
130.8
53.868
140.7
47.591
150.3
40.176
160.8
33.139
170.8
28.809
180
27.461
189.6
28.912
199.1
33.102
210
40.395
219.2
47.456
229.3
53.951
239.4
56.565
249.1
54.665
259.4
49.404
269.1
43.148
279.4
37.269
289.2
33.55
299.4
33.064
309.3
36.287
319.2
42.249
329.7
50.445
339.1
59.359
349.4
67.87
359.8
71.619
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Discussion
During the lab the purpose was to use Chemdraw to draw structures and rotate the bond angles to
find the dihedral angle and the corresponding energy of the molecule every 10 degrees until 360 degrees was reached. The graphs of the substances corresponded to the amount of energy that each bond produced. The local maxima for butane was at 0 degrees, 120 degrees, 240 degrees, and 360 degrees. The local minima for butane was 70 degrees, 180 degrees, 290 degrees. For 2,3-dimethylbutane the local maxima was 0.6 degree, 120.8 degrees, 239.4 degrees, and 359.8 degrees. The local minima for 2,3-dimethylbutane is 70.6 degrees, 180 degree, and 299.4 degrees. The local maxima for 2-methylbutane is 0.4 degrees, 120.9 degrees, 240.7 degrees, and 330.9 degrees. The local minima of 2-methylbutane is 60.4 degrees, 180 degrees, 290.8 degrees, and 360.8 degrees. In comparison the graphs shows the different energy that corresponds to the Newman projection of each substance. When two large atoms are next to each other they create tension which leads to an eclipsed projection having more energy than a staggered projection. This can be shown in the graph as well and for such reason I believe that the maxima and minima for each compound was what is to be expected. Possible errors that could potentially alter the data would have been the accuracy in collecting data. When conducting the experiment it was a challenge keeping consistent numbers when evaluating the bond angles. In conclusion the observation of angles with their energy was observed and compared to one another. This affected their Newman projections and their corresponding energies as seen in the graph.
References
Bump, Charles. (2007).
Organic Laboratory Experiments: Semi and Microscale Investigations in
General Organic Chemistry. Mason, Ohio.
Libretexts. (2016, July 21)/ 2.10: Rotation Occurs About Carbon-Carbon Single Bonds. Retrieved from https://chem.libretexts.org/Textbook_Maps/Organic_Chemistry/Map
%3A_Organic_Chemistry_(Bruice)/02%3A_An_Introduction_to_Organic_Compounds
%3A_Nomenclature%2C_Physical_Properties%2C_and_Representation_of_Structure/
2.10%3A_Rotation_Occurs_About_Carbon-Carbon_Single_Bonds
Strain. (2012, June 20). Retrieved October 11, 2018 from http://www.chem.ucla.edu/~harding/notes/strain_01.pdf
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C₁
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- Consider the compound C₂H₃N. Which one of the structures in Figure 4 is the best representation of this compound based on your current knowledge? * 1 - A 2- B 3 - C 4- D 5 - All these structures are good representations of the compound.arrow_forward3 4 ✓ 5 6 ✓ 8 9 10 Draw a skeletal ("line") structure for each of the molecules below. Be sure your structures show the important difference between the molecules. = 1 2 54°F Sunny Check key CHON Cl You can drag the slider to rotate the molecules. Click and drag to start drawing a structure. Search '☐ : Ö 00. Ar Π Save For Later Submit Assignment © 2024 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility 6:24 PM 3/25/2024 PREarrow_forwardBond Angles in an Organic Molecule II The random letter labels in this diagram of allylcyanide are to be associated with the corresponding bond angle (or other property of the nearest atom). H H H dc H- a H b C=N Match the following (but do not select any individual letter more than once): CCC angle ~109.5° HCH angle ~120º CCC angle ~120° HCH angle ~109.5° bond angle ~180° 3. 3 3 •arrow_forward
- Structural Isomers: In the next part you will learn a little about structural isomers and how to draw them. Structural isomers are compounds with the same molecular formula, but different bonding arrangements or connectivities. In other words, the atoms are connected in a different order. For example, there are 2 different compounds with the molecular formula C4H10. They are given below: H H-C- H -H H H HHH H- H H-C -H Η ΗΗ H H Do you see how the atoms are bonded in a different order in the 2 structures? So they are structural isomers. C3H12 Find three different molecular structures, isomers, with this formula. (Hint: Remember the C rule where every C atom needs to have 4 bonds.) C2H60 Find two different molecules with this formula. (Hint: What are the 2 ways you can C5H10 How many structural isomers can you find for this formula? (Hint: Notice that 2 H atoms have been removed. This means that there is EITHER 1 double bond OR there is a ring structure.) Try to provide at least 4…arrow_forwardPlease include the picture with the charges of the bonds + elementsarrow_forwardF3 Use the following Lewis diagram for propene to answer the questions: HI 11 2 3 Remember that geometry refers to the geometry defined by the atoms, not the electron pairs. The geometry about atom 1 is The geometry about atom 2 is The geometry about atom 3 is Submit Answer $ 4 R F F4 % H 5 Use the References to access important values if needed for this question. Retry Entire Group F5 T G Cengage Learning Cengage Technical Support ^ 6 MacBook Air F6 9 more group attempts remaining Y H & 7 U * 00 8 FB ( 9 K F9 0 P Previous Email Instructor F11arrow_forward
- CLG 11 – Delocalized Electrons I (10/12/21) 1. Draw three important contributing resonance structures for each of the following ions. Show all electrons including non-bonding and bonding pairs and indicate formal charges. Indicate which resonance structure would contribute the most and which would contribute the least to each of the resonance hybrids. H H H O N C C N O N C C N O N C C N н н н H N C O H H N C O H HNCO н 2. Draw four additional resonance contributors for each of the following ions. :OCH3 :ö:0 Harrow_forward1. How many isomers hexane has? 04 Os 03 2. Which one of the following compounds contains tertiary (3) carbon atoms? O butane O propane O 22-dimethylbutane O 23-dimethylbutane 3. How many primary (1°) hydrogen atoms the molecule of 2,2-dimethylpropane has? 09 04 OS O 12arrow_forwardExamine the highlighted bond in the structure below. Select all the pictures in the table that correctly show possible 3-dimensional arrangements of the atoms on both sides of the highlighted bond. If there are none, please check the box below the table that says: "None of the above." + H₂N H HI N H H H CH₂ CH, CH₂ H =CH₂ H H H H H FCH₂ CH₂ H CH3 CH3 H 7 HI N H C=CH₂ CH3 NH,=C=CH, X ola Ararrow_forward
- Molecular Models P Methane- CH4 Ethene- C2H4 Ethyne -C₂H2 Benzene C6H6 OR btw Ms Draw one view of these four molecules and indicate the bond angles. Upload a photo of your drawing below.arrow_forward11 Understanding H atoms in a skeletal structure Suppose all the chlorine atoms in this molecule are replaced by hydrogen atoms: CI Draw a skeletal ("line") structure of the new molecule. Be sure you follow all the usual rules for drawing skeletal structures. Click and drag to start drawing a structure. O X 0: Aarrow_forwardActivi The U app.101edu.co Maps YouTube ! F1 Q A Z T @ 2 Begin 0 F2 W S Aktiv Modu Modu Dr. Sc Ak x Mail b My Q G 17 out C Solved UO New S 1set S Question 9 of 48 Provide the molecular formula for the skeletal drawing shown below. A) C₂H₂N B) C₂H₂N 3 8 C) C₂H₂N 8 NH₂ D) C₂H₂N 4 9 E) C₂H, N X H #3 80 F3 E D $ 4 तं C ♂ F4 R LL F 67 5⁰ % ઞ 5 F5 را Bayo G rattar F11 { [ + 11 ? 1 K Ratta U ✰ F12 } ]arrow_forward
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