tertiary alkyl halide
Quick Summary
A tertiary alkyl halide is a chemical compound where the carbon atom bonded to a halogen (like fluorine, chlorine, bromine, or iodine) is also directly bonded to three other carbon atoms. This structure influences how these compounds react.1
Tertiary alkyl halides are generally less reactive in nucleophilic substitution reactions compared to primary or secondary alkyl halides. This is due to steric hindrance, where the three surrounding carbon groups block the approach of a nucleophile to the central carbon atom. Instead, they tend to undergo elimination reactions when treated with a strong base, forming alkenes. The carbon-halogen bond in alkyl halides is polar, with the carbon having a partial positive charge and the halogen a partial negative charge. Reactivity also increases with the size of the halogen, with iodides being the most reactive and fluorides the least.231
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organohalogen compoundStructure and physical propertiesclassified as primary, secondary, or tertiary according to the degree of substitution at the carbon to which the halogen is attached. In a primary alkyl halide, the carbon that bears the halogen is directly bonded to one other carbon, in a secondary alkyl halide to two, and in a tertiary…
Read Moreclassified as primary, secondary, or tertiary according to the degree of substitution at the carbon to which the halogen is attached. In a primary alkyl halide, the carbon that bears the halogen is directly bonded to one other carbon, in a secondary alkyl halide to two, and in a tertiary…
Read More- organohalogen compoundNucleophilic substitution
…in turn react faster than tertiary alkyl halides (RR′R″CX). When the substituents R, R′, and R″ are small—e.g., R = R′ = R″ = H in CH3X—the transition state is not very crowded, and the nucleophile displaces the leaving group from carbon rapidly. Successive replacement of R, R′, and R″…
Read More…in turn react faster than tertiary alkyl halides (RR′R″CX). When the substituents R, R′, and R″ are small—e.g., R = R′ = R″ = H in CH3X—the transition state is not very crowded, and the nucleophile displaces the leaving group from carbon rapidly. Successive replacement of R, R′, and R″…
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