Isoprene reaction

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Isoprene (2-methyl-1,3-butadiene)

Isoprene (2-methyl-1,3-butadiene) reacts with the following:
(1) hydrogen chloride (1 mole equivalent) in ether
(2) deuterium chloride (1 mole equivalent) in ether
(3) bromine (1 mole equivalent) in carbon tetrachloride
(4) excess hydrogen gas in the presence of a PtO2 catalyst
(5) excess mercury (II) acetate and methanol followed by sodium borohydride
(6) excess ozone followed by zinc and acetic acid
How should the structures of the obtained products from each of the reagents be drawn?

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Large quantities of volatile organic compounds (VOC) are produced by terrestrial and marine biota and subsequently released to the atmosphere. Most of the chlorine atoms in the lower atmosphere react with these organic compounds to produce hydrogen chloride. Indeed, measured loss rates of some organic species (in particular, the butanes, propane, dimethyl sulfide, and alkyl nitrates) have been used to estimate ambient concentrations of chlorine atoms in marine air. In addition to the hydrogen-abstraction reactions that produce hydrogen chloride, some organic species degrade via chlorine-addition reactions to form chlorinated products. Although such reactions have not been conclusively demonstrated to proceed in ambient air, various pathways are likely based on laboratory experiments. For instance, recent work demonstrates that isoprene, a ubiquitous VOC emitted by both terrestrial and marine biota, reacts with atomic chlorine via Cl addition to produce 1-chloro-3-methyl-3-butene-2-one (C5H7OCl) and three of its isomers. In the future, this compound may serve as a useful diagnostic of Cl-atom reactions in ambient air. Similar pathways may contribute to the large wet-deposition fluxes of chloroacetates and other organochlorine compounds reported by A. Grimvall and co-workers .

01) Reaction class...Alkyl Halides via Electrophylic Addition of Hydrogen Halides uses HX and ether
Historically, the addition of HX to a double bond has been described as Markonikov addition reaction: The halogen(-X)group is attached to the more substituted carbon, while the -H group is attached to the less substituted carbon.
The mechanism of this reaction proceeds through an achiral carbocation intermediate. The most stable carbocation (tertiary>secondary>primary) forms, and hence the ...