Problem

Reaction of tert-butyl pentyl ether [CH3CH2CH2CH2CH2OC(CH3)3] with HBr forms 1 -bromopenta...

Reaction of tert-butyl pentyl ether [CH3CH2CH2CH2CH2OC(CH3)3] with HBr forms 1 -bromopentane (CH3CH2CH2CH2CH2Br) and compound H. H has a molecular ion in its mass spectrum at 56 and gives peaks in its IR spectrum at 3150–3000, 3000–2850, and 1650 cm‒1. Propose a structure for H and draw a stepwise mechanism that accounts for its formation.

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