Which pair of products would result from the acid cleavage of tert-butyl propyl ether with excess concentrated HBr at an elevated temperature?

Which pair of products would result from the acid cleavage of tert-butyl propyl ether with excess concentrated HBr at an elevated temperature? Correct Answer tert-butyl bromide and propyl bromide

Ether + HX → Alkyl halide + Alcohol, Halide attacks at less hindered site to produce alkyl halide. Clearly the SN2 is not in play here, as the tertiary carbons are much too hindered for a backside attack. However, tertiary carbocations are relatively stable – and “ionization” (i.e. loss of a leaving group) leaves us with an alcohol (R-OH) and a tertiary carbocation, which can then be attacked by iodide ion to give R-I. Again, if excess HI is present then that alcohol will be converted into an alcohol. We’ll have more about that to say in a few posts actually.
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