Benzylic Reactivity
Benzylic bromides undergo SN1 faster than alkyl bromides due to:
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More halogen organics Practice Questions
Which substrate reacts fastest via SN1 in aqueous ethanol?
Which substrate reacts fastest via SN1 in aqueous ethanol?
SN2 rate decreases in order:
SN2 rate decreases in order:
Chlorobenzene is less reactive than alkyl chloride in nucleophilic substitution because:
Chlorobenzene is less reactive than alkyl chloride in nucleophilic substitution because:
Sandmeyer reaction converts anilines to aryl bromides via intermediate:
Sandmeyer reaction converts anilines to aryl bromides via intermediate:
Strong bulky base (t-BuOK) acting on 2-bromobutane favors formation of:
Strong bulky base (t-BuOK) acting on 2-bromobutane favors formation of:
Wurtz reaction is less suitable for synthesis of unsymmetrical alkanes because:
Wurtz reaction is less suitable for synthesis of unsymmetrical alkanes because:
Carbylamine test gives foul smell indicating presence of:
Carbylamine test gives foul smell indicating presence of:
Formation of Grignard reagent fails in presence of:
Formation of Grignard reagent fails in presence of:
Elimination-addition (benzyne) mechanism is favored by treatment of chlorobenzene with:
Elimination-addition (benzyne) mechanism is favored by treatment of chlorobenzene with:
Best leaving group among given (in SN1):
Best leaving group among given (in SN1):
Chloroform stored with ethanol forms phosgene slowly; ethanol is added to:
Chloroform stored with ethanol forms phosgene slowly; ethanol is added to:
Finkelstein reaction converts R–Cl to R–I using NaI in acetone because:
Finkelstein reaction converts R–Cl to R–I using NaI in acetone because:
About This Question
- Subject
- chemistry
- Chapter
- halogen organics
- Topic
- benzylic reactivity
- Difficulty
- Medium
- Year
- 2025
Solution
Correct Answer:
Resonance stabilization of benzylic carbocation
- Intermediate: In an SN1 reaction, the rate depends on how easily the metal-halogen bond breaks to form a carbocation.
- Benzylic System: In benzyl bromide (C6H5CH2Br), the resulting carbocation (C6H5CH2+) is adjacent to a benzene ring.
- Resonance: The positive charge on the methylene carbon is delocalized into the ortho and para positions of the aromatic ring through resonance.
- Stability: This resonance stabilization significantly lowers the activation energy for the first step, making benzylic halides exceptionally reactive in SN1 processes.
This medium difficulty chemistry question is from the chapter halogen organics, covering the topic of benzylic reactivity. It appeared in the 2025 exam.
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