# OChem Issue: Tosylation

## Homework Statement

Predict the major product in the following reaction (Hint: Consider intra-molecular reaction)

## Homework Equations

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.

## Homework Statement

Predict the major product in the following reaction (Hint: Consider intra-molecular reaction)

## Homework Equations

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.

A screenshot of the molecule in Marvin Sketch is attached

#### Attachments

• Screen Shot 2015-01-17 at 2.08.22 PM.png
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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.

My original thought was stability, but I am not sure. We were never shown an example problem where there was any more than one -OH group in class, nor were we shown what could happen if there are two oxygen-centric functional groups. I just do not know how to go about dealing with them since we only worked one or two problems with run-of-the-mill 1 and 2 prime alcohols.

Bystander