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CAIE A-Level Chemistry A2 29.2 Characteristic Organic Reactions Questions

Practise classifying electrophilic substitution and addition–elimination mechanisms from complete reaction evidence.

Syllabus
2028–2030
Course
Chemistry 9701
Level
A2

Exam points

  • name the mechanism from the bond changes and sequence rather than from the reagent or product alone
  • form the required electrophile with a Lewis acid and retain the corresponding negatively charged species
  • use curly arrows from an electron pair or bond and include charges, intermediates and regenerated species

Covered syllabus points

29.2.1—Terminology associated with types

Question 1

[Maximum number: 1]

Cumene is an aromatic hydrocarbon used in the synthesis of other useful chemicals.

cumene

cumene

Cumene can be synthesised via a Friedel-Crafts alkylation reaction, as shown in Fig. 5.2.

Fig. 5.2

Fig. 5.2

Name the mechanism involved in the Friedel-Crafts alkylation shown in Fig. 5.2.

Question 2

[Maximum number: 1]

Name the mechanism of the reaction forming compound E.

Question 3

[Maximum number: 3]

The reaction of phenylethanone with 1,4-dibromobutane, BrCH2CH2CH2CH2Br\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}, in the presence of FeBr3\mathrm{FeBr}_{3} is shown in Fig. 6.2.
phenylethanone

Fig. 6.2

Fig. 6.2

The mechanism of this reaction is similar to that of the alkylation of benzene.

Complete the mechanism in Fig. 6.3 for the reaction of phenylethanone with BrCH2CH2CH2CH2+\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2}^{+}ions.

Include all relevant curly arrows and charges.
Draw the structure of the organic intermediate.

Fig. 6.3

Fig. 6.3

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