IB Chemistry SL 3.4 Electron Pair Sharing Reactions Questions

Use IB Chemistry SL questions to identify electron-pair donors and acceptors, draw curly-arrow mechanisms and predict organic products.

Exam points

Identify electron-rich nucleophiles and electron-deficient electrophiles, and classify Lewis bases and Lewis acids by the electron pair they donate or accept.
Show heterolytic fission with a full double-barbed curly arrow, assigning the correct positive and negative ionic fragments and distinguishing it from homolysis.
Deduce nucleophilic substitution products by replacing the leaving group, preserving the carbon skeleton and drawing curly arrows from the electron pair source.
Explain electrophilic attack on an alkene π bond, write addition equations with water, halogens or hydrogen halides, and determine the product connectivity.

Covered syllabus points

3.4.1—Nucleophiles 3.4.2—Nucleophilic substitution 3.4.3—Heterolytic fission 3.4.4—Electrophiles 3.4.5—Electrophilic addition to alkenes 3.4.6—Lewis acid-base theory 3.4.7—Coordination bond formation 3.4.8—Complex ions

[Maximum number: 3]

Chlorine undergoes many reactions.

(a)

Predict, giving a reason, whether ethane or chloroethane is more reactive.

[ 1 ]

chloroethane AND C-Cl bond is weaker/ $324 \mathrm{~kJ} \mathrm{~mol}^{-1}$ than C-H bond $/ 414 \mathrm{~kJ} \mathrm{~mol}^{-1}$

OR

chloroethane AND contains a polar bond

Marking guidance:

Accept "chloroethane AND polar".

(b)

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

[ 1 ]

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

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.

(c)

Deduce the nucleophile for the reaction in d(iii).

[ 1 ]

hydroxide «ion»/ $\mathrm{OH}^{-}$

Marking guidance:

Do not accept NaOH.

[Maximum number: 1]

Which row correctly shows heterolytic fission?

Original rows A–D showing Br–Br bond fission.

Row A

Row B

Row C

Row D

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Covered syllabus points

Question 1

Question (a)

Question (b)

Question (c)

Question 2