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

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In summary, the difference in reactivity between t-butyl chloride and isopropyl chloride in undergoing substitution reactions is due to the extra carbon present in t-butyl chloride, making it a secondary halide. This leads to the substitution taking off a hydrogen atom instead of a chlorine atom. Addition reactions, such as formation of 2-methylpropanol, can still occur with isopropyl chloride.
  • #1
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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  • #2
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.
 
  • #3
That's a trick question.
 

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

1. What is the difference between t-butyl and isopropyl substitutions?

T-butyl and isopropyl are both alkyl groups, meaning they are made up of carbon and hydrogen atoms. The main difference between them is their structure and size. T-butyl has a branched structure with three carbon atoms, while isopropyl has a straight chain with only one carbon atom branching off.

2. How do the physical properties of substances change when t-butyl or isopropyl groups are substituted?

The presence of t-butyl or isopropyl groups can impact the physical properties of a substance. T-butyl groups tend to increase the boiling point of a substance due to their larger size and branching structure, while isopropyl groups can slightly decrease the boiling point. Additionally, both groups can contribute to the hydrophobicity (water-repelling) of a molecule.

3. Which substitution is more commonly used in organic chemistry reactions?

T-butyl and isopropyl substitutions are both commonly used in organic chemistry reactions, however, t-butyl is more commonly used. This is because t-butyl groups are more stable and less reactive than isopropyl groups, making them more useful in certain reactions.

4. How do t-butyl and isopropyl substitutions affect the reactivity of a molecule?

The presence of t-butyl or isopropyl groups can affect the reactivity of a molecule in different ways. T-butyl groups are bulky and hinder the approach of other molecules, making them less reactive. Isopropyl groups, on the other hand, are smaller and more reactive due to their ability to donate electrons to other molecules.

5. Can t-butyl and isopropyl substitutions be found in natural compounds?

T-butyl and isopropyl groups can be found in natural compounds, although they are less common compared to other alkyl groups. T-butyl groups can be found in some plant compounds, while isopropyl groups can be found in some essential oils and amino acids.

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