Chapter 6: Problem 144

Indicate how you would synthesize each of the following compounds from any one of the given organic starting materials and inorganic reagents. Specify reagents and the reaction conditions. Starting materials: propylene, isobutylene.

Short Answer

Expert verified

To synthesize 2-butanol from propylene, perform a hydroboration-oxidation reaction using diborane (B2H6) followed by oxidation with hydrogen peroxide (H2O2). To obtain 2-chloropropane from propylene, perform a hydrohalogenation reaction with hydrogen chloride (HCl). Lastly, to synthesize 2-methyl-1-butene from isobutylene, create a Grignard reagent from isobutylene and magnesium, react with formaldehyde, and then perform a dehydration reaction using concentrated sulfuric acid (H2SO4).

Step by step solution

Hydroboration-Oxidation of Propylene

To synthesize 2-butanol from propylene, we need to add water across the double bond to obtain an alcohol. We can use the hydroboration-oxidation reaction for this purpose. React propylene with diborane (B2H6) in the presence of tetrahydrofuran (THF) to form a trialkyl borane intermediate.

Oxidation with Hydrogen Peroxide

To complete the synthesis, treat the trialkyl borane intermediate with hydrogen peroxide (H2O2) in the presence of sodium hydroxide (NaOH) as a base. This will result in the formation of 2-butanol. #Example 2: Synthesis of 2-chloropropane from propylene#

Hydrohalogenation of Propylene

To form 2-chloropropane from propylene, we need to add a chlorine atom across the double bond. This can be done using the hydrohalogenation reaction. React propylene with hydrogen chloride (HCl) in the presence of an organic solvent like diethyl ether. The final product will be 2-chloropropane. #Example 3: Synthesis of 2-methyl-1-butene from isobutylene#

Grignard Reaction

First, prepare a Grignard reagent from isobutylene by reacting it with magnesium metal in the presence of anhydrous ether. This will result in the formation of the corresponding isobutyl magnesium halide (IsobutylMgX).

Reaction with Formaldehyde

Next, react the isobutyl magnesium halide (IsobutylMgX) with formaldehyde (HCHO) in the presence of anhydrous conditions. This reaction will form a primary alcohol after the addition of water or an aqueous acid.

Dehydration Reaction

In the final step, treat the primary alcohol formed in the previous step with a strong acid such as concentrated sulfuric acid (H2SO4) at a relatively high temperature, around 100-150 °C. The dehydration reaction will occur, resulting in the formation of 2-methyl-1-butene as the product.

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Indicate how you would synthesize each of the following compounds from any one of the given organic starting materials and inorganic reagents. Specify reagents and the reaction conditions. Starting materials: propylene, isobutylene.

Short Answer

Step by step solution

Hydroboration-Oxidation of Propylene

Oxidation with Hydrogen Peroxide

Hydrohalogenation of Propylene

Grignard Reaction

Reaction with Formaldehyde

Dehydration Reaction

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