Question

ORGANIC CHEM

Several reagents and several organic structures are shown below. Construct a multistep synthetic route from the reactant 2-methyl-1-butene to the product3-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 structurewill 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 vicinalhalohydrin, 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 eliminationreactions, make sure that the reactions follow Markovnikov's and Zaitsev's rules.uploaded image
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Answer #1

General guidance

Concepts and reason

To synthesize 3-bromo-2-methyl-2-butanol from 2-methyl-1-butene by using the given list of reagents and products.

Fundamentals

Conversion of 2-methyl-1-butene to 3-bromo-2-methyl-2-butanol occurs in three steps. They are,

1.Alkyl halide formation

2.Elimination

3.Halohydrin formation

Step-by-step

Step 1 of 3

The reaction is,

BrHBrCH2Cl22-methylbut-1-ene2-bromo-2-methylbutane

Explanation | Common mistakes | Hint for next step

2-methylbut-1-ene reacts with HBr,CH2Cl2{\\rm{HBr,}}\\;{\\rm{C}}{{\\rm{H}}_{\\rm{2}}}{\\rm{C}}{{\\rm{l}}_{\\rm{2}}} to form 2-bromo-2-methylbutane.

Step 2 of 3

The reaction is,

BrEtO Kt2-bromo-2-methylbutane2-methylbut-2-ene

Explanation | Hint for next step

Potassium ethoxide is strong base, it reacts with 2-bromo-2-methylbutane to form 2-methylbut-2-ene. This is reaction is called elimination reaction.

Step 3 of 3

The reaction is,

\u043e\u043dBr2H2O3-bromo-2-methylbutan-2-ol2-methylbut-2-ene

Thus, the synthetic route is,

OHEto KBr2H20HBrCH2C2Br2-methylbut-1-ene3-bromo-2-methylbutan-2-ol


2-methylbut-2-ene reacts with Br2,H2O{\\rm{B}}{{\\rm{r}}_{\\rm{2}}}{\\rm{,}}\\;{{\\rm{H}}_{\\rm{2}}}{\\rm{O}}to form 3-bromo-2-methyl-2-butanol.

Answer

Thus, the synthetic route is,

OHEto KBr2H20HBrCH2C2Br2-methylbut-1-ene3-bromo-2-methylbutan-2-ol

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