Why Can T-Butyl Chloride Undergo Substitution but Isopropyl Chloride Cannot?

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SUMMARY

T-butyl chloride (C4H9Cl) can undergo substitution reactions to form 2-methylpropanol (C4H9OH), while isopropyl chloride (C3H7Cl) cannot. The key difference lies in the structure of the compounds; T-butyl chloride is a tertiary halide, allowing for stable carbocation formation during substitution. In contrast, isopropyl chloride is a secondary halide, which does not favor substitution due to steric hindrance and the stability of the resulting carbocation. This distinction is crucial in understanding the reactivity of these alkyl halides.

PREREQUISITES
  • Understanding of alkyl halides and their classifications (primary, secondary, tertiary)
  • Knowledge of substitution reactions in organic chemistry
  • Familiarity with carbocation stability and mechanisms
  • Basic concepts of nucleophilic attack and steric hindrance
NEXT STEPS
  • Study the mechanisms of nucleophilic substitution reactions (SN1 and SN2)
  • Research the stability of carbocations and factors affecting their formation
  • Explore the differences between primary, secondary, and tertiary alkyl halides
  • Learn about related reactions such as elimination and addition reactions
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Chemistry students, organic chemists, and anyone interested in understanding the reactivity of alkyl halides and substitution mechanisms.

physics(L)10
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Homework Statement


T-butyl chloride can undergo substitution reaction to create C4H9OH, but isopropyl chloride cannot. Why is this?


Homework Equations





The Attempt at a Solution


I'm guessing it has to do with the extra carbon. Maybe since it is a secondary halide, the substitution takes the H off instead of the Cl?
 
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physics(L)10 said:

Homework Statement


T-butyl chloride can undergo substitution reaction to create C4H9OH, but isopropyl chloride cannot. Why is this?


Homework Equations





The Attempt at a Solution


I'm guessing it has to do with the extra carbon. Maybe since it is a secondary halide, the substitution takes the H off instead of the Cl?

Well, you can form 2-methylpropanol from IPA via things like metallation and addition of formaldehyde, but this is addition, not substitution. So the only thing that's relevant here is the number of carbons, in my opinion.
 
That's a trick question.
 

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