IB Chemistry SL Reactivity 3.4.2 Nucleophilic Substitution

Practise predicting nucleophilic substitution products from the attacking nucleophile and departing leaving group. Track the electron pair that forms the new carbon–nucleophile…

Exam points

identify the electron-deficient carbon bonded to the leaving group as the attack site
replace the leaving group with the nucleophile while preserving the carbon skeleton
show new-bond formation and leaving-group departure with correctly sourced curly arrows

[Maximum number: 1]

Chlorine undergoes many reactions.

Write the equation for the reaction of chloroethane with a dilute aqueous solution of sodium hydroxide.

$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}(\mathrm{l})+\mathrm{OH}^{-}(\mathrm{aq}) \rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}(\mathrm{aq})+\mathrm{Cl}^{-}(\mathrm{aq})$

OR
$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}(\mathrm{l})+\mathrm{NaOH}(\mathrm{aq}) \rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}(\mathrm{aq})+\mathrm{NaCl}(\mathrm{aq})$

Marking guidance:

Accept use of $\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{Cl}$ and $\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH} / \mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}$ in the equation.

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3.4.2—Nucleophilic substitution question 1