CAIE A-Level Chemistry 33.3.4 Hydrolysis of Acyl, Alkyl and Aryl Chlorides
Practise ranking chloride hydrolysis and explaining the order through electron deficiency and C–Cl bonding.
- Syllabus
- 2028–2030
- Course
- Chemistry 9701
- Level
- A2
Exam points
- rank acyl chloride as easiest, alkyl chloride intermediate and aryl chloride hardest to hydrolyse
- link fast acyl-chloride attack to the strongly δ+ carbonyl carbon bonded to two electronegative atoms
- link aryl-chloride resistance to chlorine lone-pair delocalisation and partial C–Cl double-bond character
33.3.4—Hydrolysis reactivity: acyl vs alkyl chlorides question 1
[Maximum number: 2]
Describe the difference in reactivity between ethanoyl chloride and chlorobenzene with water.
Explain your answer.
chlorobenzene is less reactive than ethanoyl chloride
- p orbital / lone pair on Cl/ -Cl will overlap / delocalise into the ring
OR C of COCl has most electron deficient OR has an electronegative oxygen atom / two electronegative atoms / electron withdrawing C=O group
- due to partial double C-Cl bond
OR C-Cl bond strengthened (more) / stronger bond between Cl and benzene / ring
OR C-Clweakened in ROCl
any two [1], all three [2]
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