prelab 9

prelab 9 - If that nucleophile is neutral a third step of...

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John Goodson Analysis of Structure and Leading Group Identity in Nucleophilic Substitution Reactions Introduction: The purpose of this experiment is to illustrate the two mechanistic extremes of substitution reactions, SN1 and SN2 reactions, and to investigate how the identity of the leaving group, the structure of the electrophile, and the structure of the solvent effect the two reactions. SN1 reactions involve a carbocation intermediate and are usually seen in reactions of secondary or tertiary alkyl halides or, under strongly acidic conditions, with secondary or tertiary alcohols. With primary alkyl halides, SN2 reactions occur instead. SN1 reactions between a carbon molecule and a nucleophile take place in two to three steps. The slow and reversible first step occurs when the carbon molecule forms a carbocation by separation of a leaving group from the carbon. Then the nucleophile reacts with the carbocation.
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Unformatted text preview: If that nucleophile is neutral, a third step of deprotonating the nucleophile must occur. SN2 reactions occur when an incoming nucleophile reacts with the alkyl halide from a direction opposite of the leaving group. As the nucleophile comes in one side of the substrate and bonds to the carbon, the halide departs from the other side. This inverts the stereochemical configuration. Example SN1: Example SN2: John Goodson Safety: Silver nitrate will stain skin and clothing. Alkyl halides are usually toxic and should not be inhaled or come into contact with skin. Sodium hydroxide can cause damage to skin and severe damage to eyes. Gloves and goggles should be work at all times. Compound 1-bromobutane 1-chlorobutane 2-bromo-2-methylpropane 2-bromobutane 1-propanol/water acetone/water ethanol/water methanol/water NaI in Acetone AgNO3 in Ethanol NaOH Phenolphthalein...
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prelab 9 - If that nucleophile is neutral a third step of...

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