Chapter 13: Problem 59
Show how to prepare each compound from 2-methyl-1-propanol. (a) \(2-\) Methylpropene (b) \(2-\) Methyl-2-propanol (c) 2 -Methylpropanoic acid, \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCOOH}\)
Short Answer
Expert verified
(a) Dehydrate with H2SO4. (b) Hydroboration-oxidation. (c) Oxidize with KMnO4.
Step by step solution
01
Dehydration of 2-methyl-1-propanol
To prepare 2-methylpropene, dehydrate 2-methyl-1-propanol by heating it with concentrated sulfuric acid (
H_2
SO_4) at around 180°C. This reaction removes a molecule of water, forming the alkene, 2-methylpropene.
02
Hydroboration-Oxidation of 2-Methylpropene
To form 2-methyl-2-propanol, start with 2-methylpropene. Perform a hydroboration-oxidation reaction. First, react 2-methylpropene with diborane (
B_2
H_6) to add a boron atom across the double bond. Then oxidize with
H_2
O_2 (hydrogen peroxide) in a basic solution to convert the boron atom into a hydroxyl group, yielding 2-methyl-2-propanol.
03
Oxidation of 2-Methyl-1-Propanol to 2-Methylpropanoic Acid
To obtain 2-methylpropanoic acid, oxidize 2-methyl-1-propanol using an oxidizing agent like potassium permanganate (
KMnO_4) or chromic acid (
H_2
CrO_4). This oxidation converts the alcohol group into a carboxylic acid, resulting in the formation of 2-methylpropanoic acid.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Alcohol Dehydration
Alcohol dehydration is a process that involves removing water (\(\text{H}_2\text{O}\)) from an alcohol compound to form an alkene. In this context, we are starting with 2-methyl-1-propanol. The alcohol is heated with a strong acid like sulfuric acid (\(\text{H}_2\text{SO}_4\)) at a high temperature (about 180°C). The acid serves as a catalyst that facilitates the elimination of water from the alcohol molecule.
Here's a quick rundown of the key points:
Here's a quick rundown of the key points:
- The hydroxyl group (-OH) is protonated by the acid, making it a better leaving group.
- Water is eliminated from the molecule, leading to the formation of a carbocation intermediate.
- This carbocation rearranges, if necessary, and then loses a proton to form the double bond characteristic of alkenes.
Hydroboration-Oxidation
Hydroboration-oxidation is an important two-step reaction process used to convert alkenes into alcohols. In this case, we use 2-methylpropene formed from the previous dehydration step. The process starts with hydroboration, where 2-methylpropene reacts with diborane (\(\text{B}_2\text{H}_6\)). This step adds boron and hydrogen across the double bond in a syn-addition manner—meaning both attach to the same side of the double bond.
The next step is oxidation, which involves treating the organoborane intermediate with hydrogen peroxide (\(\text{H}_2\text{O}_2\)) in a basic solution, usually sodium hydroxide (\(\text{NaOH}\)). This converts the carbon-boron bond into a carbon-hydroxyl group, forming 2-methyl-2-propanol.
The next step is oxidation, which involves treating the organoborane intermediate with hydrogen peroxide (\(\text{H}_2\text{O}_2\)) in a basic solution, usually sodium hydroxide (\(\text{NaOH}\)). This converts the carbon-boron bond into a carbon-hydroxyl group, forming 2-methyl-2-propanol.
- Hydroboration: syn-addition of B and H.
- Oxidation: replacement of B with OH using \(\text{H}_2\text{O}_2\) and base.
Alcohol Oxidation
Alcohol oxidation is a chemical process that transforms an alcohol into a carboxylic acid by increasing the oxidation state of the carbon atom. For secondary and tertiary alcohols, oxidation typically results in ketones or no reaction; however, primary alcohols like 2-methyl-1-propanol will form carboxylic acids.
In the exercise task, 2-methyl-1-propanol is oxidized to form 2-methylpropanoic acid. The reaction is carried out using strong oxidizing agents, such as potassium permanganate (\(\text{KMnO}_4\)) or chromic acid (\(\text{H}_2\text{CrO}_4\)). These reagents are powerful enough to convert the primary alcohol into a fully oxidized carboxylic acid, while simultaneously balancing the redox process.
In the exercise task, 2-methyl-1-propanol is oxidized to form 2-methylpropanoic acid. The reaction is carried out using strong oxidizing agents, such as potassium permanganate (\(\text{KMnO}_4\)) or chromic acid (\(\text{H}_2\text{CrO}_4\)). These reagents are powerful enough to convert the primary alcohol into a fully oxidized carboxylic acid, while simultaneously balancing the redox process.
- Primary alcohol oxidation leads to a carboxylic acid.
- Common oxidizing agents are \(\text{KMnO}_4\) or \(\text{H}_2\text{CrO}_4\).
Alkene Formation
Alkene formation is a process often resulting from the dehydration of alcohols. It involves the creation of a carbon-carbon double bond. In our exercise, 2-methyl-1-propanol is dehydrated to form 2-methylpropene.
The transformation involves a carbocation intermediate following the loss of water. This step is crucial as it sets up the stage for subsequent reactions like hydroboration-oxidation.
The transformation involves a carbocation intermediate following the loss of water. This step is crucial as it sets up the stage for subsequent reactions like hydroboration-oxidation.
- Involves water removal to form double bonds.
- Step involves carbocation creation which stabilizes before forming the alkene.
Carboxylic Acid Synthesis
Carboxylic acid synthesis from alcohol refers to the transformation of an alcohol group into a carboxyl functional group (\(-\text{COOH}\)). In our specific case, we take 2-methyl-1-propanol and oxidize it to form 2-methylpropanoic acid.
This conversion is generally accomplished in one step through the application of a strong oxidizing agent. These reagents ensure that the alcohol is completely oxidized, leading to the corresponding acid.
This conversion is generally accomplished in one step through the application of a strong oxidizing agent. These reagents ensure that the alcohol is completely oxidized, leading to the corresponding acid.
- The hydroxyl group is converted fully into carboxylic group.
- Oxidizing agents provide the necessary oxygen atoms.