Alkyl Halides Lab Report

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If carbocations rearrange during the intermediate phase, the product obtained will be a partial racemic mixture, where the maximum amount of product reflects the most stable carbocation intermediate thru rearrangement. Due to the relative stability of the carbocation, only tertiary alkyl halides can perform SN1 reactions, as shown below. Primary, secondary, and tertiary alcohols can react through substitution but only with hydrobromic acid (HBr), hydrochloric acid (HCl) and hydroiodic acid (HI) because they are good nucleophiles (electron rich atoms). Based on the experiment’s chemical equation: 2-methylcyclohexanol 1-bromo-1-methylcyclohexanol 1-bromo-2-methylcyclohexanol
(3o alkyl halide) (2o alkyl halide)
The goal of the experiment was to alter a secondary alcohol to isomeric alkyl halides through SN1 dehydration synthesis with hydrobromic acid. Based on the chemical equation, products obtained were 1-bromo-1-methylcyclohexanol (thru 1,2-hydride shift rearrangement) and 1-bromo-2-methylcyclohexanol (no rearrangement). Using a halogenated acid, the reaction can be controlled and analyzed to determine the primary carbocation formed.
Procedure
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After adding three boiling chips, 10 mL of 48% hydrobromic acid was also added to the round bottom flask and swirled for 15 seconds to reactants in the flask. The reactants were clamped to a ring stand and a pre-set reflux apparatus with clear hoses attached to the condenser. The voltage regulator was set to 40 to begin water flow through the condenser and the application of heat, so the solvent can boil. The reaction was set to reflux for 30 minutes. Upon completion, the round bottom flask cooled for three minutes in a beaker filled with room temperature water and again in a beaker with ice cold

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