alkylate sodium saccharin to N-ethylsaccharin with iodoethane in an aprotic solvent N‚N dimethylformamide. Nucleophiles in this experiment will react better in an aprotic solvent. Aprotic solvents have dipoles due to its polar bonds but they do not have H atoms that can be donated into a H-bond. The anions which are the O- and N- of sodium saccharin are not solvated therefore are “naked” and the reaction is not inhibited and preceded in an accelerated rate. The reaction was an SN2 reaction. Since the
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Title: Reaction of Iodoethane with Sodium Saccharin- Ambient Nucleophile Dates Performed: February 21 + 28‚ 2013 Date Submitted: March 14‚ 2013 Abstract: The product ratio of N-ethylsaccharin to O-ethylsaccharin that occurred due to alkylation with iodoethane at 80 oC was determined to be 81.5% to 18.5%‚ respectively‚ based on an analysis of the 1H NMR spectrum that was collected. The melting point range of 87.8-94.7 oC also indicated that the mixture was largely composed of N-ethylsaccharin
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Saccharin is one of the most disputed sugar substitutes in the United States today. Since 1977‚ it has been regarded as potentially carcinogenic ("Saccharin"‚ 1999). The sweetness of saccharin compared to sugarcane is utterly amazing. When measured up to sugarcane‚ saccharin is 550 times as sweet in its pure state. Also‚ it is estimated to have a sweetening power of 375 times that of sugar ("Saccharin"‚ 2000)! This drug may be amazing‚ but some people say that it causes a dangerous disease‚
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carry out the alkylation of sodium saccharin with iodo-ethane and analyze the product mixture to determine the structure of the major product. Sodium saccharin is made from the base catalyzed de protonation of saccharin. This nucleophilic reaction is special because the nucleophilic atom can be oxygen or nitrogen and the leaving group is iodide ion. The solvent used in this reaction is very important for determining the rate of nucleophilic substitution reaction. Polar protic solvents such as water
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Competing Nucleophiles Table of results: Area (mm²) Percent composition 1-bromobutane 511 85.02% 1-chlorobutane 90 14.98% 2-bromobutane 432.25 78.63% 2-chlorobutane 117.5 21.37% 2-bromo-2-methylpropane 280 37.58% 2-chloro-2-methylpropane 465 62.42% Discussion: 1. In 1-butanol Base on the data table‚ 1-bromobutane dominated the composition of 85.02%‚ which indicates the conclusion that the mechanism for 1-butanol is SN2‚ and bromide is a better nucleophile. The first
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Competitive Nucleophiles Introduction: The purpose of this experiment was to compare the relative nucleophilicities of chloride ions and bromide ions in two different reactions. One reaction involved n-butyl alcohol and the other involved t-pentyl alcohol. We performed the reactions and compared the percentages of alkyl chloride and alkyl bromide in the product. To perform this experiment‚ we used methods including heating reaction mixture under reflux‚ extraction using a separatory funnel
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staying neutral. Due to an amines basicity‚ reaction with an acid is very easy and forms a positively charged ammonium ion. As well as being a strong base‚ amines are also quite good nucleophiles. When the nitrogen is directly attached to one or two R groups is more nucleophillic than when directly attached to a hydrogen atom. The reason behind this is due to the electron donating ability of the alkyl group. However‚ the increasing strength of the nucleophile proves difficulty when added
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Katie Smith April 11‚ 2013 Competitive Nucleophiles Introduction The purpose of this experiment was to compare the nucleophilicities of chloride and bromide ions toward the n-butyl and t-pentyl alcohols. We were able to analyze this by using refractometry to measure the amounts of alkyl chloride and alkyl bromide in each reaction. Experiment Scheme (Procedure A) To begin the experiment‚ we assembled a reflux apparatus in the fume hood with a 100 mL round bottom flask and a condenser
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Competitive Nucleophiles With 1-Butanol In this experiment you will determine the nucleophile strength of bromide ion vs. chloride ion in their reaction with 1-butanol in acidic solution. The reaction is shown below. The reagents are a convenient source of HBr and HCl. The reaction is an SN2 reaction with H2O as the leaving group and Cl- and Br- as the nucleophiles. The molar amounts of Cl - and Br- are equal‚ so the better nucleophile will lead to more product. You will analyze the amounts of 1-bromobutane
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Title: Competing Nucleophiles (Exp 24‚ pp 211-221‚ pp 808-823‚ pp 836-842) Purpose: The purpose of this experiment is to determine the nucleophilic strength of chloride and bromide ions as it reacts with 1-butanol (n-butyl) and 2-methyl-2-propanol (t-butyl alcohol) under SN1 and SN2 conditions. Method: 40 g of ice and approximately 30 ml of sulfuric acid is cautiously added to a 100 mL beaker respectively. Weigh 7.6 g of ammonium chloride and 14.0 g of ammonium bromide and place it in
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