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Questions and Answers
What is the primary difference between haloalkanes and haloarenes?
What is the primary difference between haloalkanes and haloarenes?
- Haloalkanes are typically more aromatic than haloarenes.
- Haloarenes are saturated compounds, while haloalkanes are unsaturated.
- Haloalkanes have halogen atoms attached to sp3 carbon atoms, whereas haloarenes have them attached to sp2 carbon atoms. (correct)
- Haloalkanes contain carbon-carbon double bonds while haloarenes do not.
Which of the following reactions is characteristic of haloalkanes?
Which of the following reactions is characteristic of haloalkanes?
- Radical chain reaction
- Elimination reaction
- Nucleophilic substitution (correct)
- Electrophilic aromatic substitution
Which property typically makes haloalkanes less reactive than haloarenes?
Which property typically makes haloalkanes less reactive than haloarenes?
- Presence of a lone pair on the halogen atom
- Lower density of haloalkanes
- Higher electronegativity of sp2 carbons compared to sp3 carbons
- Greater C-X bond strength in haloalkanes (correct)
Which type of halogenation reaction is favored in the production of haloarenes?
Which type of halogenation reaction is favored in the production of haloarenes?
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What is a common method for the preparation of haloalkanes?
What is a common method for the preparation of haloalkanes?
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Study Notes
Haloalkanes vs Haloarenes
- Haloalkanes are alkyl halides, where the halogen atom is attached to the carbon atom of an aliphatic chain.
- Haloarenes are aryl halides, where the halogen atom is directly bonded to a carbon atom in an aromatic ring.
Reactions of Haloalkanes
- Nucleophilic substitution reactions are characteristic of haloalkanes.
- In a nucleophilic substitution reaction, the halogen atom is replaced by a nucleophile, which is an electron-rich species.
Reactivity of Haloalkanes
- Haloalkanes are less reactive than haloarenes due to the presence of the electron-rich aromatic ring in haloarenes.
- The electron density in the ring stabilizes the positive charge that develops on the carbon atom during the reaction.
Aromatic Halogenation
- Electrophilic aromatic substitution is the favored method for producing haloarenes.
- In this reaction, the aromatic ring acts as a nucleophile and attacks an electrophile, such as a halogen molecule.
Haloalkane Preparation
- Free radical halogenation is a common method for the preparation of haloalkanes, particularly with alkanes in the presence of sunlight.
- This reaction involves the formation of free radicals, which are highly reactive species that can abstract hydrogen atoms from alkanes, leading to the formation of haloalkanes.
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