Н до GB3 EtOH Br H H Br H Br

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 18E
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Reaction B
H
Br
EtOH
H Br
Figure 2 - Reaction Scheme B. In this method, stilbene is brominated using pyridinium bromide.
Ethanol is used as the solvent.
40.0 mL of ethanol and 2.00 g of (E)-stilbene were placed in a 125 mL Erlenmeyer flask. The mixture was
heated on a hot plate to dissolve the stilbene, after which 4.00 g of pyridinium tribromide was added to
the mixture. After heating while stirring for 5 minutes, the Erlenmeyer flask was removed from heat, and the
dibromide product was allowed to crystallize as the flask cooled to room temperature. Next, the mixture was
chilled in an ice bath, and the product was collected by vacuum filtration, washing the crystals with 5.00 mL
of ice-cold methanol. The product was allowed to air-dry, and obtained as white, needle-like crystals.
Table 3: Usage and Waste Data for Scheme B
Properties
Amounts Used
Excess / Waste
Moles
Compound MW (g/mol)
Mass (kg)
(mol)
Stilbene
11.1
180.25
2.00 kg
Ethanol
Pyridinium
4g
tribromide
Methanol
Product
-H
Brs
Density Volume
(g/mL)
(L)
n/a
-
40 ml
5 mL
Br. H
Excess
(mol)
0
-H
Waste
Mass (kg)
0
Transcribed Image Text:Reaction B H Br EtOH H Br Figure 2 - Reaction Scheme B. In this method, stilbene is brominated using pyridinium bromide. Ethanol is used as the solvent. 40.0 mL of ethanol and 2.00 g of (E)-stilbene were placed in a 125 mL Erlenmeyer flask. The mixture was heated on a hot plate to dissolve the stilbene, after which 4.00 g of pyridinium tribromide was added to the mixture. After heating while stirring for 5 minutes, the Erlenmeyer flask was removed from heat, and the dibromide product was allowed to crystallize as the flask cooled to room temperature. Next, the mixture was chilled in an ice bath, and the product was collected by vacuum filtration, washing the crystals with 5.00 mL of ice-cold methanol. The product was allowed to air-dry, and obtained as white, needle-like crystals. Table 3: Usage and Waste Data for Scheme B Properties Amounts Used Excess / Waste Moles Compound MW (g/mol) Mass (kg) (mol) Stilbene 11.1 180.25 2.00 kg Ethanol Pyridinium 4g tribromide Methanol Product -H Brs Density Volume (g/mL) (L) n/a - 40 ml 5 mL Br. H Excess (mol) 0 -H Waste Mass (kg) 0
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