188k views
2 votes
What is the product formed in the acid-catalyzed hydration of 3-methyl-1-butene?

1) 3-methyl-2-butanol
2) 3-methyl-1-butanol
3) 2-methyl-2-butanol
4) 2-methyl-1-butanol

User Isaias
by
8.0k points

1 Answer

2 votes

Final answer:

The product formed in the acid-catalyzed hydration of 3-methyl-1-butene is 2-methyl-2-butanol. This is determined by applying Markovnikov's rule, where the hydroxyl group attaches to the more substituted carbon, creating a more stable carbocation intermediate.

Step-by-step explanation:

The product formed in the acid-catalyzed hydration of 3-methyl-1-butene can be determined using Markovnikov’s rule, which states that in an addition reaction of a proton acid to an asymmetric alkene, the acid's hydrogen attaches to the carbon with the greater number of hydrogen atoms, and the hydroxyl group (or other non-hydrogen group) attaches to the carbon with the fewer hydrogen atoms, leading to the formation of the more stable carbocation intermediate.

Applying this rule to 3-methyl-1-butene and considering the hydration process (addition of water), the hydrogen atom from the acid catalyst would add to the carbon atom with more hydrogen atoms already attached (which in this case is the carbon number 2 in the butene molecule) and the hydroxyl group (OH) would attach to the carbon with fewer hydrogen atoms (carbon number 1 in the molecule). Therefore, the product of the hydration of 3-methyl-1-butene would be 2-methyl-2-butanol.

The carbocation formed on the more substituted carbon during this process is more stable, which leads to the formation of this product rather than a product with the hydroxyl group on the less substituted carbon.

User Zhaoqing
by
7.7k points