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Chapter 22: Problem 150

Alcohols are very useful starting materials for the production of many different compounds. The following conversions, starting with 1-butanol, can be carried out in two or more steps. Show the steps (reactants/catalysts) you would follow to carry out the conversions, drawing the formula for the organic product in each step. For each step, a major product must be produced. See Exercise 62. (Hint: In the presence of \(\mathrm{H}^{+}\), an alcohol is converted into an alkene and water. This is the exact reverse of the reaction of adding water to an alkene to form an alcohol.) a. 1 -butanol \(\longrightarrow\) butane b. 1-butanol \(\longrightarrow 2\) -butanone

Short Answer

Expert verified
a. Conversion of 1-butanol to butane: 1) 1-butanol + \(\mathrm{H}^{+}\) (from H2SO4 or H3PO4) \(\longrightarrow\) 1-butene + H2O 2) 1-butene + H2/Pd/C \(\longrightarrow\) butane b. Conversion of 1-butanol to 2-butanone: 1) 1-butanol + HBr \(\longrightarrow\) 1-bromobutane + H2O 2) 1-bromobutane + CH3COOK (from KOH and ethanoic acid) \(\longrightarrow\) 2-butanone + KBr

Step by step solution

01

Formation of 1-butene from 1-butanol

To convert 1-butanol to 1-butene, we need to use a dehydrating agent. Typically, we can use concentrated sulfuric acid (H2SO4) or concentrated phosphoric acid (H3PO4) as a dehydrating agent with heat applied. In this step: 1-butanol + \(\mathrm{H}^{+}\) (from H2SO4 or H3PO4) \(\longrightarrow\) 1-butene + H2O
02

Hydrogenation of 1-butene to butane

To convert 1-butene to butane, we need to carry out a hydrogenation reaction, which involves the addition of hydrogen (H2) across the carbon-carbon double bond. This can be achieved using a catalyst like palladium on carbon (Pd/C) or platinum on carbon (Pt/C) under mild temperature and pressure conditions. In this step: 1-butene + H2/Pd/C \(\longrightarrow\) butane b. Conversion of 1-butanol to 2-butanone
03

Formation of 1-bromobutane from 1-butanol

To convert 1-butanol to 1-bromobutane, we need to utilize a halogenation reaction. We can use hydrobromic acid (HBr) as the halogenating agent. In this reaction: 1-butanol + HBr \(\longrightarrow\) 1-bromobutane + H2O
04

Formation of 2-butanone from 1-bromobutane

To convert 1-bromobutane to 2-butanone, we can perform a nucleophilic acyl substitution with ethanoic acid. We can use a strong base like potassium hydroxide (KOH) as the nucleophile, and water as the solvent. In this reaction: 1-bromobutane + CH3COOK (from KOH and ethanoic acid) \(\longrightarrow\) 2-butanone + KBr

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Most popular questions from this chapter

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