Oraganic Chemistry I: Oxidizing Methoxybenzyl Alcohol 1) Explain why a phase-tra
ID: 911068 • Letter: O
Question
Oraganic Chemistry I: Oxidizing Methoxybenzyl Alcohol
1) Explain why a phase-transfer catalyst is used when oxidizing methoxybenzyl alcohol using NaOCl.
2)
substance quantity molar mass (g/mole) bp (°C)
bleach (NaOCl) 20 mL
dichloromethane 18 mL 84.93 40°C
ethyl acetate 40 mL 88.11 76—77°C
magnesium sulfate,
anhydrous 1 g 120.37
methoxybenzaldehyde
(reaction product) 136.15 248°C
p-methoxybenzyl alcohol 1.5 g 138.15
sodium chloride,
saturated solution 20—30 mL
sodium hydroxide,5% 20 mL
tetrabutylammonium
hydrogen sulfate 0.15—0.2 g 339.54
Using the data in the Reagents and Properties table above, calculate the theoretical yield of methoxybenzaldehyde in grams, assuming you start with 1.50 g of the alcohol. (Assume the alcohol is the limiting reactant). Please, show your work.
Explanation / Answer
1) methoxybenzyl alcohol will be soluble in oreganic solvent, whereas NaOCl will be soluble in water. Hence to bring these two reactants together a phase-transfer catalyst shall be used.
In this reaction, Tetrabultyleammonium hydrogen sulphate (TBAS) shall be used as a phase-transfer catal.
2) The Balance euation for the above reation is
C6H4Cl-CH2-OH + NaOCl --> C6H4Cl-CH=O
That means 1 mole of methoxybenzyl alcohol will react with 1 mole of NaOCl
From given data No. of moles of methoxybenzyl alcohol = 1.5 g/ 138.15 g/mole = 0.01086 moles
Hence no. of moles of methoxybenzaldehyde = 0.01086 moles
the theoretical yield = 0.01086 moles x 136.15 g/mole =1 .478 g
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