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Which of the following compounds undergoes an SN1 reaction most readily?

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Question: Which of the following compounds undergoes an SN1 reaction most readily?

Options:

  1. 1-bromopropane
  2. 2-bromopropane
  3. 3-bromopropane
  4. 1-bromo-2-methylpropane

Correct Answer: 3-bromopropane

Solution:

Tertiary alkyl halides like 3-bromopropane stabilize the carbocation intermediate formed during the SN1 mechanism, making them more reactive.

Which of the following compounds undergoes an SN1 reaction most readily?

Practice Questions

Q1
Which of the following compounds undergoes an SN1 reaction most readily?
  1. 1-bromopropane
  2. 2-bromopropane
  3. 3-bromopropane
  4. 1-bromo-2-methylpropane

Questions & Step-by-Step Solutions

Which of the following compounds undergoes an SN1 reaction most readily?
  • Step 1: Understand what an SN1 reaction is. It is a type of nucleophilic substitution reaction that involves two main steps.
  • Step 2: Identify the first step of the SN1 reaction, which is the formation of a carbocation. This happens when the leaving group (like a bromine atom) departs from the alkyl halide.
  • Step 3: Recognize that the stability of the carbocation is crucial. More stable carbocations are formed from tertiary alkyl halides (where the carbon is attached to three other carbons).
  • Step 4: Compare different types of alkyl halides. Tertiary alkyl halides (like 3-bromopropane) are more stable than secondary or primary alkyl halides because they have more surrounding carbon atoms to help stabilize the positive charge.
  • Step 5: Conclude that since tertiary alkyl halides form more stable carbocations, they undergo SN1 reactions more readily than primary or secondary alkyl halides.
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