Di- n- pentyl ether can be converted to 1- bromopentane by treatment with HBr through essentially a(n) mechanism.

SN1 mechanism

Explanation:

The mechanism of this reaction is shown in the image attached.

The Di- n- pentyl ether is first protonated. The CH3(CH2)4OH is now a good leaving group as shown.

The attack of the bromide ion on the cation formed completes the mechanism to yield 1- bromopentane as shown in the mechanism.

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