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2018 H2 Chem P1 Q21 — Introduction to Organic Solution

Introduction to Organic 2018 A-Level H2 Chemistry · Paper 1 · Q21

Question

Which pair of species are carbocations?
  1. A\([CH_3CO]^+, \quad [CH_3OH_2]^+\)
  2. B\([(CH_3)_3C]^+, \quad [(CH_3)_4N]^+\)
  3. C\([CH_3CO]^+, \quad [(CH_3)_3C]^+\)
  4. D\([(CH_3)_4N]^+, \quad [CH_3OH_2]^+\)
Correct answer: C

Video Solution

Explanation

The answer is C.
A carbocation is a positive ion in which the positive charge sits on a carbon atom.
• \([\text{CH}_3\text{CO}]^+\) (the acylium ion, \(\text{CH}_3\text{-}\overset{+}{\text{C}}\text{=O}\)): the positive charge is on the carbonyl carbon, so it is a carbocation.
• \([(\text{CH}_3)_3\text{C}]^+\): the positive charge is on the central carbon bonded to three methyl groups (a tertiary carbocation).
• \([\text{CH}_3\text{OH}_2]^+\): oxygen has formed a third bond (to an extra \(\text{H}^+\)), so the positive charge is on O, not C.
• \([(\text{CH}_3)_4\text{N}]^+\): nitrogen has formed four bonds, so the positive charge is on N (a quaternary ammonium ion), not C.
• A is wrong: \([\text{CH}_3\text{OH}_2]^+\) has its positive charge on oxygen.
• B is wrong: \([(\text{CH}_3)_4\text{N}]^+\) has its positive charge on nitrogen.
• D is wrong: neither species is a carbocation; the charges are on N and O.

Worked solution diagram

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