Question

Several reagents and several organic structures are shown below. Construct a multistep synthetic route from the reactant 2-methyl-1-butene to the product 3-bromo-2-methyl-2-butanol by dragging the appropriate pieces into the bins. Note that each bin will hold only one item, and not every given reagent or structure will be used.

HINT:

Start by locating the structures of 2-methyl-1-butene and 3-bromo-2-methyl-2-butanol and placing them in their bins. Note that the final product is a vicinal halohydrin, since it has halogen and hydroxyl substituents on adjacent carbons.

Which of the given compounds can be converted to the bromohydrin in one step, and what reagent should be used? When you consider addition or elimination reactions, make sure that the reactions follow Markovnikov\'s and Zaitsev\'s rules.

Answer 1

Reaction:

Step-1:

In addition of the hydrogen halide to the alkene, the H atom bonds to the less substituted carbon atom.

Step-2:

Here, the alkyl halide reacts with a strong base and favors the elimination product. This step is followed by E2 mechanism.

Step-3:

This step undergoes addition reaction, the reagent serves as a electrophile and results in the additon of Br and OH to the double bond.

Answer 2