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Chapter 19: Q18P (page 635)

When o-phthalaldehyde is treated with base, o-(hydroxymethyl)benzoic acid is formed. Show the mechanism of this reaction.

Short Answer

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Formation of desired product

Step by step solution

01

Cannizaro reaction

Cannizzaro reaction is a base-induced disproportionation reaction. In this reaction, two moles of aldehyde react to give one molecule of carboxylic acid and another molecule of primary alcohol.

02

 Mechanism of this reaction

Initially, the addition of hydroxyl group to O-phthaladehyde takes place, then expulsion and addition of hydride ion occur. This shift of proton takes place followed by protonation to get the desired compound.

Formation of the desired product

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Most popular questions from this chapter

When crystals of pure α-glucose are dissolved in water, isomerization occurs slowly to produce β-glucose. Propose a mechanism for isomerization.

In light of your answer to Problem 19-46, propose a mechanism for the formation of 3, 5-dimethylisoxazole from hydroxylamine and 2,4-pentanedione

The 1HNMR spectrum shown is that of a compound isomeric with the one in Problem 19-81. This isomer has an IR absorption at 1730 cm-1. Propose a structure.

[Note: Aldehyde protons (CHO) often show low coupling constants to adjacent hydrogens, so the splitting of aldehyde signals is not always apparent.]

Name the following aldehydes and ketones:

Propose structures for ketones or aldehydes that have the following H1NMR spectra:

(a)C10H12O

localid="1656491160287" IR:1710cm-1

(b) localid="1656491164732" C6H12O3

localid="1656491168876" IR:1715cm-1
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