Chapter 27: Problem 90
The compound obtained by the reaction of ethene with diborane, followed by hydrolysis with alkaline hydrogen peroxide is (a) ethanal (b) ethanol (c) triethyl boride (d) propanol
Short Answer
Expert verified
The compound is ethanol (b).
Step by step solution
01
Identify the Reaction
Ethene (\(\text{C}_2\text{H}_4\)) reacts with diborane (\(\text{B}_2\text{H}_6\)). This is a hydroboration-oxidation reaction. It is a two-step process where the alkene is first converted into an organoborane intermediate.
02
Understanding Hydroboration
During hydroboration, diborane is added to ethene. This results in the formation of a trialkylborane where boron atom bonds to one of the carbon atoms of the alkene through syn-addition, typically giving a primary alkyl borane product. For ethene, the product is ethyl borane (\(\text{C}_2\text{H}_5\text{B}\)).
03
Perform Oxidation and Hydrolysis
The organoborane undergoes oxidation and is hydrolyzed in an alkaline hydrogen peroxide (\(\text{H}_2\text{O}_2\)) environment. This converts the C-B bond into a C-OH bond, forming the alcohol. The final product from ethene via hydroboration-oxidation is ethanol (\(\text{C}_2\text{H}_5\text{OH}\)).
04
Consider Options
Given the options, identify the compound that matches the final outcome of the conversion. The conversion forms ethanol.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Ethene
Ethene, often represented as \(\text{C}_2\text{H}_4\), is a small molecule famously known as the simplest alkene. It is characterized by its double bond, making it highly reactive. The structure of ethene consists of two carbon atoms connected by a double bond, with each carbon atom bonded to two hydrogen atoms. This double bond is central to its chemical reactivity.When ethene participates in chemical reactions, such as in hydroboration, its double bond offers a site for addition. This means other atoms or compounds can add across this double bond, converting the alkene into an alkane derivative. The reactivity of ethene is further leveraged in various industrial applications because the molecule can easily open its double bond to form products like alcohols, plastics, and other important chemicals.
- Basic structure: Two carbon atoms double-bonded, each with two hydrogen atoms.
- Highly reactive due to the double bond, allowing for addition reactions.
- Commonly used as a starting material to produce alcohols through hydroboration-oxidation.
Diborane
Diborane, with the formula \(\text{B}_2\text{H}_6\), is a boron-hydride compound that plays a critical role in hydroboration reactions. As a source of boron, it allows for the addition of hydrogen and boron across double bonds of alkenes like ethene.In diborane, each boron atom is bonded to several hydrogen atoms, allowing it to form organoborane compounds when reacting with alkenes. The unique bonding in diborane facilitates syn-addition, meaning that the boron and hydrogen add to the same side of the alkene’s double bond. This characteristic makes diborane especially useful in organic synthesis to create specific boron-containing intermediates.
- Structure: Comprised of two boron atoms and six hydrogen atoms.
- Facilitates syn-addition, adding boron and hydrogen to the same side of a double bond.
- Used to form organoborane compounds, which are precursors to alcohols.
Alcohol Formation
Alcohol formation from alkenes involves a two-step reaction known as hydroboration-oxidation. This method is both efficient and selective for converting alkenes into alcohols, often versatile and valuable compounds in chemistry.
Firstly, in the hydroboration phase, diborane reacts with an alkene, like ethene, to form an organoborane intermediate. In this process, boron attaches to the less crowded carbon, following Markovnikov's rule that describes which hydrogen or other substituents add to which carbons in reactions involving alkenes.
Secondly, in the oxidation and hydrolysis step, the organoborane compound is treated with hydrogen peroxide in an alkaline solution. This step transforms the boron-carbon bond into a carbon-oxygen bond, producing an alcohol. For instance, the reaction of ethene through this pathway ultimately yields ethanol. This transformation is extremely useful, as it results in an alcohol that is non-toxic and has widespread uses in industries as a solvent and disinfectant.
- Involves a two-step reaction: hydroboration followed by oxidation.
- Converts alkenes into alcohols efficiently, observing regioselectivity.
- The final product from ethene is ethanol, a valuable industrial alcohol.