Question

Integrated Problem 20.72

Draw a plausible mechanism for the following transformation:

For the mechanism, draw the curved arrows as needed. Include lone pairs and charges in your answer. Do not draw out any hydrogen explicitly in your products. Do not use abbreviations such as Me or Ph.

Draw Step 4 of the mechanism.

Answer 1

The possible mechanism may be H OH H₂CH3 OH 0 0 + H2O - > ells :0 +H2O +ho Mechanism OH цас сну Hochz attack of 4* from bidrog - Ö t carboxylic OH O L -OH ot Ol ormation of co 017 GH C H₂ 3 formation of H H OH 5. membered rin. 0 oH + dissociation ď side chain :OH 1 ② removal of + LSAPO otol tu O OH -CH3 CHO Oremoval of on the e Hot O