Which of the following alkyl halides will form the most stable carbocation upon ionization?
A
(ethyl chloride)
B
(tert-butyl chloride)
C
(methyl chloride)
D
(n-propyl chloride)
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1
Identify the type of carbocation formed by each alkyl halide upon ionization. Ionization involves the loss of the halide ion (Cl⁻), leaving behind a carbocation at the carbon previously bonded to chlorine.
Classify each carbocation as primary, secondary, or tertiary based on the number of alkyl groups attached to the positively charged carbon. For example, methyl chloride forms a methyl carbocation (no alkyl groups), ethyl chloride forms a primary carbocation, n-propyl chloride forms a primary carbocation, and tert-butyl chloride forms a tertiary carbocation.
Recall that carbocation stability increases in the order: methyl < primary < secondary < tertiary. This is due to the inductive effect and hyperconjugation from alkyl groups that help stabilize the positive charge.
Compare the carbocations formed from each alkyl halide and determine which has the greatest number of alkyl substituents stabilizing the positive charge. The more alkyl groups attached, the more stable the carbocation.
Conclude that the alkyl halide forming the tertiary carbocation (tert-butyl chloride) will produce the most stable carbocation upon ionization.