Predict the products of organic reaction sequence

[![reaction sequence](https://i.stack.imgur.com/OSH4h.png)](https://i.stack.imgur.com/OSH4h.png)


This is a reaction sequence involving alcohols, phenols, halides, alkenes ,alkanes etc , and the task is to identify all the compounds A to E


The few things I was able to identify :


1. The compound ***C*** gives immediate reaction with the Lucas Reagent (ZnCl₂+HCl)therfore it must be a tertiary alcohol or it must produce a highly stable carbocation.
2. Reaction of alc.KOH after addition of HBr on ***C*** suggests that ***D*** must be at least an alkyl
bromide
3. In the conversion from ***D*** to ***B*** , step 1 produces an alkene , which then is probably
undergoing a reaction by H⁺ to form isopropyl grp , which then gives the **Friedel craft** alkylation reaction to form Cumene as suggested by the lewis acid catalyst AlCl₃ and then in next step by looking at the reagents I can predict the reaction to be the **Cumene peroxide** method of preparing phenols


[![cumene peroxide method](https://i.stack.imgur.com/qCv4h.png)](https://i.stack.imgur.com/qCv4h.png)


4. Therefore ***B*** must be phenol or a phenol derivative and ***E*** must be a Ketone, Acetone to be precise
5. Now , LiAlH₄ reduces acetone to isopropyl alcohol
6. I think in the conversion from ***D*** to ***B*** using KMnO₄ and NaOH/CaO , first oxidation occurs and then decarboxylation


The problem is the molecular weight of isopropyl alcohol will not come out to be 32 , and I am not able to guess the structures accurately as there might be possibilities of some extra non participating groups on ***B*** ,***C*** and ***D***


