Chloride Ions Vs Bromine Case Study

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2. In the contest of these two reactions, which is the better nucleophile, chloride ion or bromide ion? Try to explain this.

Bromine is a better nucleophile. The chloride ion is more polar since it is above bromine on the periodic table and is more prone to hydrogen bonding due to its smaller size. Chloride ions are worse than bromine ions for nucleophilic attack, because the chloride ions are fully solvated and are not as available to attack. This is why Bromine ion is better nucleophile because is less electronegative and is willing to give up electrons.

3. What is the principal organic by-product of these two reactions?


4. A student left a mixture of some alkyl halides (RCI and RBr) in an open container for
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This occurs because the sample vaporized into the gas phase and is placed into a capillary under controlled temperature and pressure. As the mobile phase and is placed into the capillary under controlled temperature and pressure. As the mobile phase is flowed through the capillary, more volatile compounds should elute first. Accordingly, the alcohol should elute last, preceded by the alkyl halide.
For example, in part A the 1-chlorobutane eluted first because it has a lower boiling point of 78°C compare to the boiling point of 1-bromobutane of 101.4 to 102.9°C. This is why the retention times were lower for 1-chlorobutane with 1.61min compare to the retention time of 1-bromobutane with 1.82min. In addition, in part B 2-chloro-2-methylbutane that has a boiling point of 85 to 86°C, eluted first and then 2-bromo-2-methylbutane that has a boiling point of 108°C. This is also seen in the retention time of the compounds where 2-chloro-2-methylbutane had a time of 1.27 min and 2-bromo-2-methylbutane 1.44 min. The property that was most important in determining relative retention times was the boiling point and the volatility of the
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