Experiment 6 Lab Report Orgo

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Experiment 6: The S N 2 Reaction- Factors Affecting S N 2 Reaction Ethny Indico Team Member: Mia Haynes Instructor (TA): Isiaih Nelson October 20 th , 2023 CHM 22106L Section: 034

Introduction: In organic chemistry, S N 2 mechanisms are common reactions used to examine substances’ reactivity and the factors that can affect it [1] . In this experiment, the specific factors that were analyzed regarding their effect on an S N 2 reaction’s rate included steric hinderance, nucleophilicity, and the nature of leaving groups. Steric hinderance can be defined as the “congestion” caused by ligands, which are ions that donate electrons to a central atom [2] . These ligands can be responsible for slowing down or completely preventing a reaction from occurring; for example, primary alkyl halides have less steric hinderance than tertiary alkyl halides. S N 2 reactions favor primary alkyl halides due to the reduced amount of steric hinderance. Nucleophilicity is another factor that must be considered when regarding how fast or efficiently a reaction may be carried out. If an element or compound acts as a stronger nucleophile than the reaction will be able to perform easier than if it were to occur with weak ones. Not only do nucleophiles have the ability to hasten or delay a reaction, but so do leaving groups. If an element is a better leaving group than the reaction will be able to occur with more ease and a precipitate will form more readily; vice versa for if it is a bad leaving group. In correlation to all three of these effects another factor that has to be considered is the type of substrate being utilized in the reaction. Primary alkyl halide substrates tend to be more reactive when in contact with a nucleophile than a tertiary alkyl halide as mentioned above. Through use of various reactions, these theoretical resulting effects can be examined and an unknown amine will also be able to be identified. The unknown amine will specifically be identified using melting point after an S N 2 reaction is carried out.

Mechanism of an S N 2 Reaction – Triethylamine and 1-Bromopropane: Possible Side Reaction that could occur During Above Mechanism: Part A – Reactions with Different Amines: Test Tube 1: Add 5 mL of the pre-prepared solvent, 20 drops of triethylamine, and 10 drops of methyl iodide. Slightly swirl Test Tube 2: Add 5 mL of the pre-prepared solvent, 20 drops of tripropylamine, and 10 drops of methyl iodide. Slightly swirl Test Tube 3: Add 5 mL of the pre-prepared solvent, 20 drops of Ethyldiisopropylamine, and 10 drops of methyl iodide. Slightly swirl Record observations of the reaction, including the time and color of ppt.

Part B – Reactions with Different Alkyl Halides: Part C – Identification of an Unknown Quaternary Ammonium Salt: Chemicals Used: Chemical Physical Properties Physical Appearance Chemical Properties Iodomethane: Molar mass 141.94 g/mol Melting point -66.5 °C Boiling point 42 °C Formula: CH 3 I Colorless liquid with a characteristic odor. Turns brown on exposure to moisture Avoid heating; otherwise chemically stable under ambient conditions Iodoethane: Molar mass 155.97 Colorless liquid Flammable liquid Test Tube 1: Add 20 drops of triethylamine and 15 drops of iodoethane. Slightly swirl Test Tube 1: Add 20 drops of triethylamine and 15 drops of 1-bromopropane. Slightly swirl Test Tube 1: Add 20 drops of triethylamine and 15 drops of 2-bromopropane. Slightly swirl Record observations of the reaction, including the time and color of ppt. Determine the melting point and percent yield of the collected product. Using provided literature values, determine which amine the unknown is In a test tube, add 40 drops of an unknown amine (unknown 2 was used), 20 drops of iodomethane and 2 mL of the pre-prepared solvent. Allow it to stand for 10-15 minutes. If the tube gets too hot, place it in an ice bath. Once the precipitate has formed, vacuum filtrate it

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