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25. Phenols

20. Phenols / Phenol Acidity / Problem 3

Problem 3

Give the reagents that will complete the synthesis shown below:

A

(i)

Step 1: a. H₂CrO₄, H₂O, 125°C, 100 atm;

Step 2: H₃O⁺ quench

Step 3: H₂SO₄, CH₃CH₂OH

(ii)

Step 1: PCl₃, CH₂Cl₂

Step 2: , NaOH

B

(i)

Step 1: a. H₂CrO₄, H₂O, 125°C, 100 atm;

Step 2: H₃O⁺ quench

Step 3: NaOH, H₂O, CH₃CH₂Cl

(ii)

Step 1: SO₂Cl₂, CH₂Cl₂

Step 2: , HCl

C

(i)

Step 1: a. CO2, NaOH, H2O, 125°C, 100 atm;

Step 2: H₃O⁺ quench

Step 3: NaOH, H₂O, CH₃CH₂Cl

(ii)

Step 1: SO₂Cl₂, CH₂Cl₂

Step 2: , NaOH

D

(i)

Step 1: a. CO₂, NaOH, H₂O, 125°C, 100 atm;

Step 2: H₃O⁺ quench

Step 3: NaOH, H₂O, CH₃CH₂Cl

(ii)

Step 1: PCl₃, CH₂Cl₂

Step 2: , HCl