Question
Tosylates are produced by the reaction of alcohols with p-toluenesulfonyl chloride, forming ____ of toluenesulfonic acid.
Answer
Tosylates are produced by the reaction of alcohols with p-toluenesulfonyl chloride, forming esters of toluenesulfonic acid.
Note: The hydroxyl groups of alcohols are fairly poor leaving groups for nucleophilic substitution reactions. However, they can be protonated, or reacted to form much better leaving groups called mesylates and tosylates.
In Summary: The leaving-group ability of a substituent correlates with the strength of its
conjugate acid. Both depend on the ability of the leaving group to accommodate negative
charge. In addition to the halides Cl2, Br2, and I2, sulfates and sulfonates (such as methane and 4 methylbenzenesulfonates) are good leaving groups. Good leaving groups are weak
bases, the conjugate bases of strong acids.
Keep this card coming back until it sticks
Sign up free and spaced repetition will bring Chapter 5: Alcohols cards back right before you forget them.
Continue studying — sign up freeMore cards in Chapter 5: Alcohols
Alcohols have the general formula ____.
The functional group ____ is referred to as a hydroxyl group.
The functional group –OH is referred to as a ____ group.
Hydroxyl groups attached to aromatic rings are called ____.
Hydroxyl groups attached to ar____e called phenols.
____ attached to aromatic rings are called phenols.