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Ch.6 - Alkyl Halides; Nucleophilic Substitution
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh.6 - Alkyl Halides; Nucleophilic SubstitutionProblem 1d,e,f
Chapter 6, Problem 1d,e,f

Classify each compound as an alkyl halide, a vinyl halide, or an aryl halide.

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Step 1: Understand the definitions of the three classifications: An alkyl halide is a compound where a halogen atom (e.g., Br, Cl, I, F) is bonded to an sp³-hybridized carbon atom. A vinyl halide is a compound where a halogen atom is bonded to an sp²-hybridized carbon atom in a double bond. An aryl halide is a compound where a halogen atom is bonded directly to an aromatic ring.
Step 2: Analyze bromocyclohexane. In this compound, the bromine atom is attached to a carbon atom in a cyclohexane ring. Since the carbon is sp³-hybridized, bromocyclohexane is classified as an alkyl halide.
Step 3: Analyze 1-bromocyclohexene. In this compound, the bromine atom is attached to a carbon atom that is part of a double bond in a cyclohexene ring. Since the carbon is sp²-hybridized, 1-bromocyclohexene is classified as a vinyl halide.
Step 4: Analyze a PCB (polychlorinated biphenyl). PCBs consist of two benzene rings connected by a single bond, with multiple chlorine atoms attached to the rings. Since the chlorine atoms are bonded directly to aromatic rings, PCBs are classified as aryl halides.
Step 5: Summarize the classifications: Bromocyclohexane is an alkyl halide, 1-bromocyclohexene is a vinyl halide, and a PCB is an aryl halide. This classification is based on the hybridization of the carbon atom to which the halogen is attached and the structural context of the compound.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Alkyl Halides

Alkyl halides are organic compounds where a halogen atom (such as chlorine, bromine, or iodine) is bonded to an alkyl group, which is a saturated hydrocarbon chain. They are characterized by the general formula R-X, where R represents the alkyl group and X is the halogen. Common examples include bromoethane and chloropropane.
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Vinyl Halides

Vinyl halides are a specific type of halogenated compound where the halogen is attached to a carbon-carbon double bond (alkene). They have the general structure R-CH=CH-X, where R is a hydrogen or alkyl group, and X is the halogen. An example is 1-bromopropene, which features a vinyl group.
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Aryl Halides

Aryl halides are compounds in which a halogen atom is bonded to an aromatic ring, such as benzene. The general structure can be represented as Ar-X, where Ar is the aryl group and X is the halogen. Examples include bromobenzene and chlorotoluene, which exhibit unique reactivity due to the stability of the aromatic system.
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Related Practice
Textbook Question

Give the structures of the following compounds.

e. 2-bromo-3-ethyl-2-methylhexane

f. isobutyl bromide

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Textbook Question

Give the structures of the following compounds.

g. cis-1-fluoro-3-(fluoromethyl)cyclohexane

h. tert-butyl chloride

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Textbook Question

Classify each compound as an alkyl halide, a vinyl halide, or an aryl halide.

(a) CH3CHCFCH3

(b) (CH3)3CBr

(c) CH3CCl3

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Textbook Question

Give the structures of the following compounds.

a. methylene iodide

b. carbon tetrabromide

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