Enrol to start learning
Reading is open to everyone. Enrolling is free, and it is what unlocks the audio lessons, practice tests and progress tracking.
9.3.4. Preparation
Interactive Audio Lesson
Unlock the classroom podcast
The transcript is above and free to read. A free account plays the conversation back.
Create a free accountToday, we're discussing how we can prepare alkenes from alkynes using partial reduction. Does anyone remember what a partial reduction means?
Is it when we reduce the triple bond to a double bond without fully saturating it?
Exactly! We use Lindlar’s catalyst for this process to achieve a cis-configuration. So, when we take ethyne and add dihydrogen gas, we get ethene. Can anyone provide the reaction for this?
Sure! It’s CH≡CH + H2 in the presence of Pd/C to produce CH2=CH2.
Great! Let’s not forget that this method is crucial in organic synthesis for creating more reactive double-bonded compounds. Now, how about the preparation from alkyl halides?
Unlock the classroom podcast
The transcript is above and free to read. A free account plays the conversation back.
Create a free accountMoving on, alkenes can also be prepared from alkyl halides through a process known as dehydrohalogenation. Who can tell me how this reaction works?
We heat the alkyl halide with alcoholic potassium hydroxide to eliminate HX and form the alkene, right?
Exactly! This is a classic beta-elimination reaction. The rate is influenced by the halogen and the type of alkyl group. What can you tell me about the reactivity order of these halides?
The order is iodine > bromine > chlorine, right? Iodine reacts the fastest.
Correct! And remember that tertiary alkyl halides undergo this reaction the fastest due to steric factors. Let’s summarize: we generate alkenes and this method is widely used in organic synthesis.
Unlock the classroom podcast
The transcript is above and free to read. A free account plays the conversation back.
Create a free accountNext, let's talk about vicinal dihalides. Can anyone explain what they are and how we convert them into alkenes?
Vicinal dihalides have two halogens attached to adjacent carbon atoms, right?
Excellent. And what’s the reaction we typically use?
We treat them with zinc to eliminate a halogen molecule and form the alkene.
Right again! The general reaction would be CH2Br–CH2Br + Zn → CH2=CH2 + ZnBr2. Can anyone summarize why this method is useful?
It provides a way to synthesize alkenes from halogenated compounds efficiently, making it important in organic synthesis.
Unlock the classroom podcast
The transcript is above and free to read. A free account plays the conversation back.
Create a free accountNow, let’s cover how we can prepare alkenes from alcohols. Is anyone familiar with how we can achieve that?
We heat alcohols with concentrated sulfuric acid? This removes water, right?
Exactly! This reaction is known as acidic dehydration. It follows a beta-elimination mechanism. Can anyone write the general reaction?
I think it’s R-OH + H2SO4 → Alkene + H2O.
Perfect! Great job. Remember how crucial it is to understand these mechanisms since they are foundational in organic chemistry.
Overview
Short Summary
This section explores the various methods of preparing alkenes from alkynes, alkyl halides, vicinal dihalides, and alcohols, highlighting the importance of these reactions in organic synthesis.
Medium Summary
In this section, we delve into the preparation methods for alkenes, encompassing techniques such as partial reduction of alkynes, elimination reactions from alkyl halides, and dehydration of alcohols. We also address the significance of understanding these methods for broader applications in organic chemistry, especially regarding the generation of compounds with double bonds.
Detailed Summary
Preparation of Alkenes
The preparation of alkenes is an essential topic in organic chemistry, particularly because alkenes are crucial intermediates in various synthetic pathways. This section outlines multiple methods of synthesizing alkenes:
1. From Alkynes
Alkynes can be transformed into alkenes through partial reduction. This is typically achieved using Lindlar’s catalyst (partially deactivated palladium on charcoal) when dihydrogen gas is added, leading to the formation of cis-alkenes. For example,
- Ethyne (acetylene) can be converted to ethene (ethylene) and
- Propyne can be converted to propene.
This reaction is significant as it allows the conversion of more triple-bonded compounds into more reactive double-bonded compounds.
2. From Alkyl Halides
Heating alkyl halides with alcoholic potassium hydroxide (KOH) induces a beta-elimination reaction, where hydrogen halide is eliminated to form alkenes. This method's rate depends on the halogen atom's nature and the alkyl group's structure, indicating tertiary alkyl halides react fastest and iodine more reactive than chlorine. Overall, the process can be summarized as:
- R-X (alkyl halide) + alcoholic KOH → Alkene + HX.
3. From Vicinal Dihalides
Vicinal dihalides, where two halogens are attached to adjacent carbons, can be converted into alkenes via dehalogenation. This reaction typically involves zinc metal:
CH2Br–CH2Br +
Reference YouTube Videos
Audio Book
Unlock the audio lesson
The script is above and free to read. A free account plays it back, in the voice you pick.
Create a free accountAlkynes on partial reduction with calculated amount of dihydrogen in the presence of palladised charcoal partially deactivated with poisons like sulphur compounds or quinoline give alkenes. Partially deactivated palladised charcoal is known as Lindlar\u2019s catalyst. Alkenes thus obtained are having cis geometry. However, alkynes on reduction with sodium in liquid ammonia form trans alkenes.
Detailed Explanation
Alkynes can be converted into alkenes through a process known as partial reduction. This involves using a specific type of catalyst called Lindlar's catalyst, which is palladised charcoal that has been treated to reduce its activity. When alkynes undergo this process, they gain a double bond while losing one of their triple bonds, resulting in alkenes. The addition of dihydrogen gas occurs, and the structure of the resulting alkene has a cis configuration, meaning the hydrogen atoms attached to the double bond are on the same side. If the alkyne is treated with sodium in liquid ammonia, a different product is formed, leading to a trans alkene structure, where the hydrogen atoms are on opposite sides of the double bond.
Examples & Analogies
Think of the alkyne compound as a rope stretched tightly between two points (the carbon atoms in the triple bond). By applying a little pressure (the dihydrogen), we can loosen the rope to form a loop (the alkene), but how we apply that pressure changes the shape of the loop. Using Lindlar's catalyst creates a loop that is more closed (cis), whereas using sodium in liquid ammonia creates a loop that is stretched out (trans).
Unlock the audio lesson
The script is above and free to read. A free account plays it back, in the voice you pick.
Create a free accountAlkyl halides (R-X) on heating with alcoholic potash (potassium hydroxide dissolved in alcohol, say, ethanol) eliminate one molecule of halogen acid to form alkenes. This reaction is known as dehydrohalogenation i.e., removal of halogen acid. Nature of halogen atom and the alkyl group determine rate of the reaction.
Detailed Explanation
Alkyl halides can be transformed into alkenes through a process called dehydrohalogenation. This occurs when the alkyl halide is heated with alcoholic potash, leading to the elimination of a hydrogen halide molecule (like HCl or HBr). The effectiveness and speed of this reaction depend on the nature of the halogen and the type of alkyl group (primary, secondary, or tertiary). Generally, tertiary alkyl halides react faster than secondary or primary ones because of their structure, which stabilizes the formation of the alkene.
Examples & Analogies
Imagine trying to unscrew a tight lid (the alkyl halide) from a jar (the solvent) while heating the jar. The resistance you face when applying force depends on how tightly the lid is stuck, similar to how the structure of the alkyl halide affects the reaction speed. When the lid finally pops loose, that\u2019s like the alkene being formed, showcasing how effective the heating can be when paired with the right tools (alcoholic potash).
Key Concepts
Core takeaways and short definitions to help you quickly recall the key ideas from this section.
Preparation from Alkynes: Alkenes can be made using partial reduction of alkynes.
Dehydrohalogenation: Alkyl halides react with alcoholic KOH to form alkenes.
Vicinal Dihalides: Can be converted to alkenes via dehalogenation with zinc.
Dehydration: Alcohols can be dehydrated to form alkenes using concentrated sulfuric acid.
Examples
Memory Aids
Interactive tools to help you remember key concepts
Stories
Flash Cards
Glossary
Alkene
A hydrocarbon containing at least one carbon-carbon double bond.
Alkyne
A hydrocarbon containing at least one carbon-carbon triple bond.
Vicinal Dihalide
A compound where two halogen atoms are bonded to adjacent carbon atoms.
Dehydrohalogenation
An elimination reaction where hydrogen halide (HX) is removed to form an alkene.
Partial Reduction
A reaction that reduces a multiple bond (triple or double) to a lower multiple bond without completely saturating it.
BetaElimination
A reaction where a double bond is formed by the elimination of adjacent atoms or groups.