Examining Substitution Reactions of Several Alcohol-Containing Compounds
Several Experiments were performed using substitutions reactions with hydrogen halides. These results and favor methods or pathways for the several alcohols were observed and will be discussed.
Introduction for all the material
Scheme 1. Substitution of 3-(m-tolyl)propan-1-ol to form 1-(3-bromopropyl )-3-methylbenzene. Aromatic materials used in this reaction has high boiling point thus the reaction was heated carefully and gently to avoid burning and decomposition of other reagents. Byproduct such as E2 elimination seen often with good leaving groups and basic nucleophiles or rearranged products, expected with alternative mechanism were unable to observed by gas chromatography or H NMR. The initial alcohol was not chiral structure thus stereochemical analysis was not needed or necessary. Adding sodium bromide and sulfuric acid had visible effect on the yield of the reaction. In this experiment, excess NaBr solid were removed due to having no important yield increase when more than 1.2 quantity of NaBr was used. Sulfuric acid was used in the experiment due to the conjugate base being very poor …show more content…
Alcohol being used in this reaction was 3-phenyl-1-propanal. 3.503 grams of alcohol with 2.884 grams of sodium bromide was added to 5 ml of 9M sulfuric acid. The mixture solution was heated under reflux condition very carefully for about 25 minutes and the temperature at the end was 65 degrees Celsius. During the solution was under reflux, solution has two layers: top layer being reddish color and bottom layer was clear. Excess NaBr solid were removed from the reaction material. The reaction material was then wash using separatory funnel with 15 ml of water and two times with 10 ml of 5% NaHCO3. 1.502 grams of sodium bicarbonate and 28.5 grams of H2O was used to obtained 20 ml of 5% NaHCO3, followed by drying the material with sodium sulfate. IR
Several Experiments were performed using substitutions reactions with hydrogen halides. These results and favor methods or pathways for the several alcohols were observed and will be discussed.
Introduction for all the material
Scheme 1. Substitution of 3-(m-tolyl)propan-1-ol to form 1-(3-bromopropyl )-3-methylbenzene. Aromatic materials used in this reaction has high boiling point thus the reaction was heated carefully and gently to avoid burning and decomposition of other reagents. Byproduct such as E2 elimination seen often with good leaving groups and basic nucleophiles or rearranged products, expected with alternative mechanism were unable to observed by gas chromatography or H NMR. The initial alcohol was not chiral structure thus stereochemical analysis was not needed or necessary. Adding sodium bromide and sulfuric acid had visible effect on the yield of the reaction. In this experiment, excess NaBr solid were removed due to having no important yield increase when more than 1.2 quantity of NaBr was used. Sulfuric acid was used in the experiment due to the conjugate base being very poor …show more content…
Alcohol being used in this reaction was 3-phenyl-1-propanal. 3.503 grams of alcohol with 2.884 grams of sodium bromide was added to 5 ml of 9M sulfuric acid. The mixture solution was heated under reflux condition very carefully for about 25 minutes and the temperature at the end was 65 degrees Celsius. During the solution was under reflux, solution has two layers: top layer being reddish color and bottom layer was clear. Excess NaBr solid were removed from the reaction material. The reaction material was then wash using separatory funnel with 15 ml of water and two times with 10 ml of 5% NaHCO3. 1.502 grams of sodium bicarbonate and 28.5 grams of H2O was used to obtained 20 ml of 5% NaHCO3, followed by drying the material with sodium sulfate. IR