Polymerization Lab Report 2
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Dec 6, 2023
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04/10/23
Polymerization Report
Results Table and Mechanism: Compound
Weight (g)
Mols
Theoretical Yield
Nylon 6-6
4.360
g
0.0642
0.0341 mol
Discussion:
The purpose of this experiment was to synthesize a polymer (Nylon 6-6) from adipoyl chloride and hexanediamide through a polymerization reaction. The polymer was drawn out of the beaker using a copper wire, this was then spun around a glass rod until there was no more product to draw out. The length of the polymer was not measured, so a percent yield was not calculated. The theoretical yield was 0.0341 moles and the mass of the (wet) polymer was 4.360 g and resulted in a total of 0.0642 moles. This experiment was very simple and there was not a lot of room for error, but some did occur. The first time running this experiment was unsuccessful, and this could be due to several reasons. One could be not adding enough sodium hydroxide to the hexanediamide. Another reason could be adding the adipoyl chloride solution too quickly, and the reaction could have taken place. Neither of those seemed to be the issue though, I believe the first container of adipoyl chloride was at fault. Most of the class struggled to form polymer from the first container. After more adipoyl chloride was made, the reaction worked and fumed (where it did not the first time around), and the color of the adipoyl chloride was much darker. Slowing down the process and making sure all the reactants were pure and correct would have resulted in a successful attempt the first time around. Questions:
1.
The hydroxide must be added to the hexanediamide solution to deprotonate the amide group to allow the reaction to continue. If sodium hydroxide was not added, the reaction would not occur because the adipoyl chloride would not be able to attack and form the polymer/nylon. 2.
3.
Chlorides are good leaving groups, so acid chlorides are more reactive than carboxylic acids. Chlorides form a weaker resonance bond with the carbonyl carbon than an ester group, so acid chlorides are more reactive than esters.
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Related Questions
Macromolecules can also be formed from cyclic monomers such as cyclic hydrocarbons, ethers, esters, amides, siloxanes, and sulfur (eight-membered ring). Thus, ring-opening polymerization is of particular interest, since macromolecules of almost any chemical structure can be prepared. Choose two of the above type polymers to explain the mechanism and chemical reaction of polymerization process.
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HO-CH2CH2OH
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H₂N
NH2
HO
་_ou
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a) Write down the reaction mechanism. What is the polymerization mechanism that it follows?
b) What are the glass transition and melting temperatures of this polymer? Describe the techniques and their principles used to determine these properties
c) How would you determine its molecular weight?
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Modify the monomers to create one repeat unit of the polymer.
NH
Incorrect
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This polymer is composed of 2 monomer units: an acid chloride and an amine. In the box below, draw the structure of both monomers.
(8-10
C
(CH₂)6-C
CH₂
어
H
n
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
• Separate structures with + signs from the drop-down menu.
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Type of polymerization that occurred?
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H H
0-C-C-0-
Choose
addition polymer
ymer involved
polyester
polyamide
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Draw three repeat units (trimer) of the polymer formed in this
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PhC(O)OOC(O)Ph (BPO)
Q
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Please don't provide handwriting solution
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What polymer is formed in this reaction, using polymer notation?
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Molecular weight data for some polymer are tabulated here.
Molecular Weight
Xi
Wi
Range (g/mol)
19000 - 34000
0.04
0.01
34000 - 49000
0.07
0.04
49000 - 64000
0.16
0.11
64000 - 79000
0.26
0.24
79000 - 94000
0.24
0.27
94000 - 109000
0.12
0.16
109000 - 124000
0.08
0.12
124000- 139000
0.03
0.05
Compute the following:
(a) the number-average molecular weight.
M,
i 72800
g/mol
(b) the weight-average molecular weight.
Mw
i
g/mol
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Draw three repeat units (trimer) of the polymer formed in this
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Assume there are hydrogen atoms on the two ends of the
trimer. Ignore inorganic byproducts.
F
F
F
T
PhC(O)OOC(O)Ph (BPO)
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Linear polymers are more water-soluble than branched ones.
True
False
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full structural form is needed for complete reaction h.w
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