Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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What is the experimental yield (grams and percentage)

Experiment: Oxidation of -Chlorotoluene to o-Chlorobenzoic acid

materials used

  • dissolved 3.35 g of KMnO4
  • 1.20 mL of 2-chlorotoluene was added to the mixture
  • 3.0 mL of concentrated hydrochloric acid (pH~2)
  • 10 mL of toluene
  • -The crystals were isolated by vacuum filtration-

Product Characterization

  • 1.15 g of the crude product

  • 0.93 g of the final product

  • M.p. (final): 139-141 oC

In the experiment, potassium permanganate is used to oxidize 2-chlorotoluene (o-chlorotoluene)
to 2-chlorobenzoic acid (o-chlorobenzoic acid). Permanganate solutions are less hazardous than
those containing chromium compounds, which are often carcinogenic.
.CH3
СООН
1. KMnO4, H,О, д
2. HСІ, Н,0
`CI
`Cl
The yield of the reaction observed in the literature (Clarke, H. T.; Taylor, E. R. Org. Synth. 1930,
10, 20) is 76-78 % before recrystallization and 65-67 % after recrystallization.
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Transcribed Image Text:In the experiment, potassium permanganate is used to oxidize 2-chlorotoluene (o-chlorotoluene) to 2-chlorobenzoic acid (o-chlorobenzoic acid). Permanganate solutions are less hazardous than those containing chromium compounds, which are often carcinogenic. .CH3 СООН 1. KMnO4, H,О, д 2. HСІ, Н,0 `CI `Cl The yield of the reaction observed in the literature (Clarke, H. T.; Taylor, E. R. Org. Synth. 1930, 10, 20) is 76-78 % before recrystallization and 65-67 % after recrystallization.
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