Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
(CH₃)₂CHCH(Cl)CH₃
IUPAC Name: 2-Chloro-3-methylbutane. Classification: Secondary (2°) alkyl halide.
CH₃CH₂CH(CH₃)CH(C₂H₅)Cl
IUPAC Name: 3-Chloro-3-methylpentane. Classification: Tertiary (3°) alkyl halide.
CH₃CH₂C(CH₃)₂CH₂I
IUPAC Name: 1-Iodo-2,2-dimethylbutane. Classification: Primary (1°) alkyl halide.
(CH₃)₃CCH₂CH(Br)C₆H₅
IUPAC Name: 1-Bromo-2,2-dimethyl-1-phenylpropane. Classification: Secondary (2°) benzylic halide.
CH₃CH(CH₃)CH(Br)CH₃
IUPAC Name: 2-Bromo-3-methylbutane. Classification: Secondary (2°) alkyl halide.
CH₃C(C₂H₅)₂CH₂Br
IUPAC Name: 1-Bromo-2-ethyl-2-methylbutane. Classification: Primary (1°) alkyl halide.
CH₃C(Cl)(C₂H₅)CH₂CH₃
IUPAC Name: 2-Chloro-2-ethylbutane. Classification: Tertiary (3°) alkyl halide.
CH₃CH=C(Cl)CH₂CH(CH₃)₂
IUPAC Name: 3-Chloro-5,5-dimethylpent-2-ene. Classification: Vinylic halide.
CH₃CH=CHC(Br)(CH₃)₂
IUPAC Name: 1-Bromo-1,1-dimethylbut-2-ene. Classification: Tertiary (3°) allylic halide.
p-ClC₆H₄CH₂CH(CH₃)₂
IUPAC Name: 1-Chloro-4-(2-methylpropyl)benzene. Classification: Aryl halide.
m-ClCH₂C₆H₄CH₂C(CH₃)₃
IUPAC Name: 1-Chloromethyl-3-(2,2-dimethylpropyl)benzene. Classification: Primary (1°) benzylic halide.
o-Br-C₆H₄CH(CH₃)CH₂CH₃
IUPAC Name: 1-Bromo-2-(1-methylpropyl)benzene. Classification: Aryl halide.
Explanation
For IUPAC naming, identify the longest carbon chain as parent, number to give lowest locants to substituents, and name substituents alphabetically. For classification: Alkyl halides have halogen on sp³ carbon of alkyl chain (1°=bonded to 1 carbon, 2°=bonded to 2 carbons, 3°=bonded to 3 carbons). Allylic halides have halogen on sp³ carbon adjacent to C=C. Benzylic halides have halogen on sp³ carbon attached to aromatic ring. Vinylic halides have halogen on sp² carbon of C=C. Aryl halides have halogen directly bonded to aromatic ring sp² carbon.