Design a procedure to accomplish an assigned oxidation reaction. Find and cite o

Question

Design a procedure to accomplish an assigned oxidation reaction. Find and cite one or more published procedures (other than your textbook) for similar alcohols to support your proposal. Your procedure must include the choice of an appropriate, selective oxidizing agent, how you would work-up the reaction, and a method to purify the product. Finally, what techniques would you use to confirm the identity of your product? Be specific, mentioning physical properties and appropriate diagnostic spectral data. To complete this assignment, all relevant prelab calculations should be performed, based on a scale of 130 mg of alcohol starting material. Write this like a technical synthetic procedure in your lab textbook (1-2 paragraphs, with commentary on the reaction separate).

4-nitrobenzylalcohol ------------> 4-nitrobenzaldehyde

Explanation / Answer

Selective oxidation of alcohol used in organic synthesis, involves reacting primary alcohol or secondary alcohol with bismuthonium salt in presence of base, and producing aldehyde or ketone respectively
Use the below data
Reaction Conditions: Time: 1 HR Temp: 25.0 DEG C
Catalyst (1) Mesityltriphenylbismuthonium tetrafluoroborate; (Ph3Bi(2,4,6-CH3-C6H2))(BF4)0.33 mmol
Catalyst (2) TMG; 1,1,3,3-Tetramethylguanidine; (Me2N)2C=NH-0.33 mmol
Solvent (1) CH2Cl2

Reactant (1) p-Nitrobenzyl alcohol-0.30 mmol
Product (1) 4-NO2C6H4CHO
Yield: 99 %

Comments: Advantages: 1) short reaction time, 2) mild conditions.

PHYSICAL PROPERTIES OF 4- NITRO BENZYL ALCOHOL :

SPECTRAL DATA OF 4-NITROBENZYL ALCOHOL :

PHYSICAL PROPERTIES AND SPECTRAL DATA FOR 4-NITROBENZYLALDEHYDE :

CRYSTALLISATION IS PURIFICATION METHOD AND TLC IS THE TECHNIQUES FOR THE IDENTIFICATION OF PRODUCT...

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