Question
Fill in the missing pieces of the chemical roadmap below.
H/HO HBr PhCOOOH Cl2 in H2O in DMF NaC=CH conc. H2SO4 in DMF
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Answer #1

HBr H/HO PhCOOOH Cl, in H20 FOK in DMF OH NaC=CH in DMF conc. H2SO4

Explanation: Reaction of alkene with H+, H2O produces more substituted alcohol as product. Reaction of alcohol with HBr gives SN1 substitution reaction and produces tertiary alkyl halide as product. Reaction of alkene with peracid produces epoxide as product. opening of epoxide with acetylide ion produces alcohol as product. Reaction of alkene with Cl2, H2O produces halohydrin as product. Dehydration of alcohol with H2SO4 produces alkene as product. t-BuOK is a strong base which abstracts acidic proton gives epoxide as product.

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