9) What would be the difference between the 4 alcohols in IR? They all show O-H, C-H sp3, and C-H aromatic bonds. The only way to tell which one is used would be by comparing the fingerprint regions to published IR spectra of each alcohol. Alcohol 2 has an aldehyde C-H group that could be seen between 2700-2800 and 2800-2900 cm-1 Only alcohol 3 will show O-H bond around 3300 cm-1 Only alcohol 1 will show C=C aromatic bonds around 1600 cm-1 10) Assuming 5.0 mL of alcohol 2 was used and 2.2 g of the product was isolated, what is the percent yield for this reaction? The product has a molar mass of 198.00 g/mol. 11) How could the percent yield be increased for this reaction? Add NaOH to neutralize the product as it forms Add a catalyst such as H2SO4 to help speed up the reaction Add a catalyst such as HCl to help speed up the reaction Cool the reaction on ice to increase the rate of reaction
9) What would be the difference between the 4 alcohols in IR? They all show O-H, C-H sp3, and C-H aromatic bonds. The only way to tell which one is used would be by comparing the fingerprint regions to published IR spectra of each alcohol. Alcohol 2 has an aldehyde C-H group that could be seen between 2700-2800 and 2800-2900 cm-1 Only alcohol 3 will show O-H bond around 3300 cm-1 Only alcohol 1 will show C=C aromatic bonds around 1600 cm-1 10) Assuming 5.0 mL of alcohol 2 was used and 2.2 g of the product was isolated, what is the percent yield for this reaction? The product has a molar mass of 198.00 g/mol. 11) How could the percent yield be increased for this reaction? Add NaOH to neutralize the product as it forms Add a catalyst such as H2SO4 to help speed up the reaction Add a catalyst such as HCl to help speed up the reaction Cool the reaction on ice to increase the rate of reaction
9) What would be the difference between the 4 alcohols in IR? They all show O-H, C-H sp3, and C-H aromatic bonds. The only way to tell which one is used would be by comparing the fingerprint regions to published IR spectra of each alcohol. Alcohol 2 has an aldehyde C-H group that could be seen between 2700-2800 and 2800-2900 cm-1 Only alcohol 3 will show O-H bond around 3300 cm-1 Only alcohol 1 will show C=C aromatic bonds around 1600 cm-1 10) Assuming 5.0 mL of alcohol 2 was used and 2.2 g of the product was isolated, what is the percent yield for this reaction? The product has a molar mass of 198.00 g/mol. 11) How could the percent yield be increased for this reaction? Add NaOH to neutralize the product as it forms Add a catalyst such as H2SO4 to help speed up the reaction Add a catalyst such as HCl to help speed up the reaction Cool the reaction on ice to increase the rate of reaction
9) What would be the difference between the 4 alcohols in IR?
They all show O-H, C-H sp3, and C-H aromatic bonds. The only way to tell which one is used would be by comparing the fingerprint regions to published IR spectra of each alcohol.
Alcohol 2 has an aldehyde C-H group that could be seen between 2700-2800 and 2800-2900 cm-1
Only alcohol 3 will show O-H bond around 3300 cm-1
Only alcohol 1 will show C=C aromatic bonds around 1600 cm-1
10) Assuming 5.0 mL of alcohol 2 was used and 2.2 g of the product was isolated, what is the percent yield for this reaction? The product has a molar mass of 198.00 g/mol.
11) How could the percent yield be increased for this reaction?
Add NaOH to neutralize the product as it forms
Add a catalyst such as H2SO4 to help speed up the reaction
Add a catalyst such as HCl to help speed up the reaction
Cool the reaction on ice to increase the rate of reaction
12) Is there another way that the product of this reaction could be isolated and purified?
Set up a co-distillation of immiscible liquids so that only the alkyl halide distills into the receiving flask.
Recrystallize the product from ethanol
Set up a co-distillation of immiscible liquids so that all impurities distill and leave just the product behind
Set up a co-distillation of immiscible liquids so that the alkyl halide is left with just water to remove
13) How would the product and the starting alcohol differ in IR?
The product should not have an O-H bond or the sp3 C-H bonds
The product should have sp3 C-H bonds and the alcohol will not
The product should not have an O-H bond, but will still have the sp3 and aromatic C-H bonds
Both have aromatic C-H bonds but only the product will have C=C aromatic bonds in the IR
Transcribed Image Text:Nucleophilic Substitutions
The following reaction was set-up as follows:
R-OH + HBr --> R-Br
Where R-OH could be one of the following possible compounds 1-4
1
1
2
3
OH
2
4
HBr (48%)
OH
3
OH
5.0 mL of the unknown alcohol was added to 15 mL of HBr (48% HBr in water) in a 150 mL Erlenmeyer flask. The reaction was covered and stirred at room temperature for
60 min. After that time, two layers could be seen in the flask. One was clear and the other was a pale yellow.
The following table has the physical properties for each of the possible alcohols and HBr. All of the alcohols are immiscible with water.
Compound
Molar mass (g/mol)
Boiling point (degC)
Melting point (degC)
28-23
136.19
202
136.19
136.19
136.19
80.91
ОН
-18
110-111
119-121
219-221
||||
Density (g/mL at 25 C)
0.973
0.975
1.001
0.973
1.49
Definition Definition Organic compounds in which one or more hydrogen atom in an alkane is replaced by a halogen atom (fluorine, chlorine, bromine, or iodine). These are also known as haloalkanes.
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