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

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter15: Benzene And Aromaticity
Section15.SE: Something Extra
Problem 52AP
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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

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
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
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