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Problems and exercisesAlkenes

1. Reactions of 2-methyl-1-phenylcyclohexene

Starting from 2-methyl-1-phenylcyclohexene, predict the outcome of the reactions in the table:

The table asks for the products of twelve reactions of 2-methyl-1-phenylcyclohexene: catalytic hydrogenation; addition of Br₂; Br₂ with excess NaCl; I₂ in water; Cl₂ in ethanol; HBr; HBr with H₂O₂; H₂O in acid; oxymercuration-demercuration; hydroboration-oxidation; ozonolysis with reductive and with oxidative work-up; MCPBA then hydrolysis; MnO₄⁻ then hydrolysis; OsO₄ then hydrolysis

2. Which reagent would you use?

Give the reagent or sequence of reagents to convert 1-methylcyclohexene into:

  1. Methylcyclohexane
  2. 1-Methylcyclohexanol
  3. trans-2-Methylcyclohexanol
  4. cis-1-Methylcyclohexane-1,2-diol
  5. 6-Oxoheptanal

3. Degrees of unsaturation

A hydrocarbon C6H10 takes up 1 mol of H2 on catalytic hydrogenation. How many rings does it have? Propose a structure.

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