Student Name: Aleycna Jerame
APPLY Experiment 15: Nucleophilic Substitution Reactions
Questions - Please answer the following questions. Limited partial credit will be given for the questions.
1. Usually, bimolecular nucleophilic substitution \( \left(\mathrm{S}_{\mathrm{N}} 2\right) \) reactions occur under basic conditions. The \( \mathrm{S}_{\mathrm{N}} 2 \) reaction of 1-butanol by a halide ion is a rare example of a \( \mathrm{S}_{\mathrm{N}} 2 \) reaction under acidic conditions. Of course, halide ions were not the only nucleophiles in your reaction medium. Draw the acidcatalyzed \( \mathrm{S}_{\mathrm{N}} 2 \) reaction mechans molecules of 1-butanol. dibutyl ether from two molecules of 1-butanol.
2. Explain the difference in boiling point between the isomers 1-chlorobutane and 2-methyl-2chloropropane in terms of structure.
Since 1-chlorobutane has stranger intermolccular forces, it requires more energy to overcome these farces 1 transition into the gaseous phese Also 1-chlonobutane is a straight-chain molecule, allowing for grecter sarface is a branched motecule, reducing the surface contact leading to weater von der wails.
3. A \( 2: 1: 1 \) mixture of 2-chloro-2-methylpropane (MW: \( 106.59 \mathrm{~g} / \mathrm{mol} \), density \( 0.866 \mathrm{~g} / \mathrm{mL}, \mathrm{bp} 85^{\circ} \mathrm{C} \) ), 1-chlorohexane (MW: \( 120 \mathrm{~g} / \mathrm{mol} \), density \( 0.87 \mathrm{~g} / \mathrm{mL} \), bp \( 133^{\circ} \mathrm{C} \) ), and 1-chlorooctane (MW: 148 \( \mathrm{g} / \mathrm{mol} \), density \( 0.87 \mathrm{~g} / \mathrm{mL} \), bp \( 183^{\circ} \mathrm{C} \) ) was injected into a GC. What is the order that the compounds will elute (flow through) the column? Please draw the chromatograph and clearly label the peaks.
4. 2-methyl-2-propanol \( (0.0100 \mathrm{~mol}) \) is reacted with \( \mathrm{NH}_{4} \mathrm{Br}(0.0175 \mathrm{~mol}) \) and \( \mathrm{NH}_{4} \mathrm{Cl}(0.0350 \mathrm{~mol}) \) in the presence of \( \mathrm{H}_{2} \mathrm{SO}_{4}(0.100 \mathrm{~mol}) \). What is the expected ratio of the products 2-bromo-2methylpropane and 2-chloro-2-methylpropane? Explain.
2-bromo-2-methylpropane: 1 Since the recction follow SN1 2-chlore-2-mcthy|propanc: 2 mectrnism be of tertiany carbocection its Cetermined by the nudeolliles \( \left(s_{0}-1, c c^{-}\right) \). And-Cl is prosont twice then- \( B r \).
UNIVERSITYATALBANY
ratiois 1:2
State University of New York
147
