Introduction to Multistep Synthesis

One of the most challenging aspects of learning organic chemistry is devising sequences of reactions that will lead from a designated starting compound to a desired product compound. This problem is an introduction to the planning of multistep syntheses. For use, you have six reactant compounds (A through F); and eight reagents (1 through 8), shown below.
Following these lists, five multistep syntheses are outlined. For each of these, certain reactants or reagents must be identified by entering an appropriate letter or number in designated answer boxes. Enter a single letter or number, indicating your choice of the best reactant or reagent, in each answer box.

Reactant Compounds: Six labeled reactants: A benzene, B acetone, C 1-propanol, D oxirane, E ethyl acetate, F acetic anhydride

Reagents

1 Jones' reagent Na₂Cr₂O₇ in H₃O⁽⁺⁾	2 PCC CrO₃ in pyridine + HCl	3 Sodium Hydride NaH	4 Sodium Borohydride NaBH₄
5 Thionyl Chloride SOCl₂	6 Phosphorus Tribromide PBr₃	7 Aluminum Trichloride AlCl₃	8 Magnesium Mg turnings in ether

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	1) reagent 2) Reactant 3) H₃O⁽⁺⁾	C₉H₁₂O₂	reagent

Reactant	reagent	C₃H₆O₂	1) reagent 2) Reactant + reagent & heat

	1) reagent 2) reagent 3) CO₂ 4) H₃O⁽⁺⁾	C₆H₁₀O₂	Reactant heating with catalytic acid

Reactant	reagent	C₃H₆O	1) NaOH solution 2) reagent 3) Reactant

Reactant	1) reagent 2) reagent	C₃H₇Br	1) reagent 2) Reactant 3) H₃O⁽⁺⁾