5) What should be the molecular formula of the product of this reaction? C9H12BrO C9H10Br C9H13Br C9H11Br

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Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
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5) What should be the molecular formula of the product of this reaction?

C9H12BrO

C9H10Br

C9H13Br

C9H11Br

6) Where is the product after the 60 min?

it did not form because this reaction cannot take place

it is the top layer in the flask

it is the bottom layer in the flask

it is the solid precipitate

7) After separating the layers, the organic layer has 1-2 scoops of anhydrous sodium sulfate added to it until it stops clumping. Why is the sodium sulfate added?

To dry the organic layer by causing the water remaining to evaporate

It is the nucleophile in this reaction

To dry the organic layer by complexing with any water that remains dissolved in it

To neutralize the acid left over from the reaction

8) Alcohol 4 is a chiral compound. If pure R-(+)-1-phenyl-propan-2-ol was used, how could the mechanism be determined?

Since it is secondary, it is unclear if it would be Sn1, Sn2, or some of both. If it was Sn1, the product should be a racemic mixture. If it was Sn2, the product should be S-(-)-1-phenyl-2-bromopropane.

Since it is tertiary, it must go through Sn2, which means the product's stereochemistry would be inverted.

Since it is primary, it must go through Sn1, which has no effect on the stereochemistry of the product. It would stay R-(+)-1-phenyl-2-bromopropane

Since it is primary, it must go through Sn1, which means the product would be a racemic mixture

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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