Which of the following compounds will undergo nucleophilic substitution via an S

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Question: Which of the following compounds will undergo nucleophilic substitution via an SN1 mechanism?

Options:

Correct Answer: 3-chloropropane

Solution:

3-chloropropane is a tertiary haloalkane, which favors the SN1 mechanism due to the formation of a stable tertiary carbocation.

Which of the following compounds will undergo nucleophilic substitution via an SN1 mechanism?

Which of the following compounds will undergo nucleophilic substitution via an SN1 mechanism?

Step 1: Identify the type of haloalkane in the question. A tertiary haloalkane has three carbon atoms attached to the carbon that is bonded to the halogen (in this case, chlorine).
Step 2: Understand the SN1 mechanism. This mechanism involves two main steps: first, the halogen leaves, forming a carbocation (a positively charged carbon), and second, a nucleophile attacks the carbocation.
Step 3: Determine if the carbocation formed is stable. Tertiary carbocations are more stable than primary or secondary ones because they are surrounded by more carbon atoms, which help stabilize the positive charge.
Step 4: Conclude that since 3-chloropropane is a tertiary haloalkane, it will undergo nucleophilic substitution via the SN1 mechanism due to the formation of a stable tertiary carbocation.

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