Predict the major product in the following reaction (Hint: Consider intra-molecular reaction)
HO2C-(CH2)3-CH(OH)-CH3 ------------cat. p-TsOH, heat----------> ???
The Attempt at a Solution
Essentially what I cannot figure out is if the tosic acid is going to replace the -OH group of the carboxylic acid, the other standalone -OH group, or both. I would assume that it would only replace one since the molecule would likely be more stable, and for that same reason I would also assume that it would replace the 2 prime -OH rather than the -OH attached to the carboxylic acid group.