10.4.3 - From Alkenes
Enroll to start learning
Youβve not yet enrolled in this course. Please enroll for free to listen to audio lessons, classroom podcasts and take practice test.
Interactive Audio Lesson
Listen to a student-teacher conversation explaining the topic in a relatable way.
Preparation of Haloalkanes: Addition of HX
π Unlock Audio Lesson
Sign up and enroll to listen to this audio lesson
Today, we'll explore how haloalkanes can be prepared from alkenes using the addition of hydrogen halides. Can anyone tell me what happens during this reaction?
Isn't it like adding H and a halide to the double bond?
Exactly! This addition generates haloalkanes. Importantly, this reaction typically follows Markovnikov's rule, which states that the hydrogen atom from HX attaches to the carbon that is already bonded to more hydrogen atoms.
Can you give us an example of Markovnikov's rule?
Sure! Take ethene reacting with HBr as an example. The product is bromoethane, where bromine attaches to the carbon with fewer hydrogens. Remember: the more stable carbocation forms in this manner!
So, stability is key here?!
Yes, stability translates to reactivity! To summarize, the addition of HX to alkenes is a crucial method for preparing haloalkanes, following Markovnikov's rule.
Preparation of Haloalkanes: Halogenation
π Unlock Audio Lesson
Sign up and enroll to listen to this audio lesson
Now let's discuss halogenation! Who can tell me what this process involves?
Isnβt that when we add a halogen like Brβ directly to the alkene?
Correct! When you react an alkene with a diatomic halogen like bromine, you get a vicinal dihaloalkane. For example, adding Brβ to ethylene produces 1,2-dibromoethane.
What's a vicinal dihaloalkane?
Great question! A vicinal dihaloalkane is a compound where two halogen atoms are bonded to adjacent carbon atoms. So this method is quite useful for creating complex organic molecules.
Is there a difference in how the reactions proceed?
Definitely! Unlike the addition of HX, halogenation does not follow Markovnikov's rule, so both halogens end up equally on either carbon.
So halogenation is more straightforward?
In terms of product distribution, yes! In summary, both addition of HX and the halogenation processes are key methods for preparing haloalkanes.
Introduction & Overview
Read summaries of the section's main ideas at different levels of detail.
Quick Overview
Standard
In this section, we discuss the preparation of haloalkanes from alkenes through two primary methods: the addition of hydrogen halides and halogenation. Each method follows specific rules like Markovnikov's rule, and they demonstrate how alkenes are converted into useful haloalkane products.
Detailed
Detailed Summary
The section outlines two methods for preparing haloalkanes from alkenes: addition of hydrogen halides (HX) and halogenation. The addition of HX to alkenes typically follows Markovnikov's rule, which states that the hydrogen atom from HX will attach to the carbon with more hydrogen substituents, resulting in a more stable product. For example, the reaction of ethylene (CβHβ) with HBr yields bromoethane (CβHβ Br).
The halogenation method involves the reaction of alkenes with diatomic halogens (like Brβ), leading to the formation of vicinal dihaloalkanes, as illustrated by the reaction of ethylene with bromine, producing 1,2-dibromoethane. Both methods are significant in synthetic organic chemistry as they provide pathways to produce haloalkanes, which serve as intermediates in various chemical reactions and applications.
Audio Book
Dive deep into the subject with an immersive audiobook experience.
Addition of HX
Chapter 1 of 2
π Unlock Audio Chapter
Sign up and enroll to access the full audio experience
Chapter Content
β’ Addition of HX:
CHβ=CHβ + HBr β CHβCHβBr
(Markovnikovβs rule applies)
Detailed Explanation
This chunk describes how alkenes react with hydrogen halides (HX), such as HBr. When ethene (CHβ=CHβ) reacts with hydrogen bromide (HBr), it forms bromoethane (CHβCHβBr). This reaction follows Markovnikovβs rule, which states that in the addition of HX to an unsymmetrical alkene, the hydrogen atom attaches to the carbon with more hydrogen atoms (or fewer substituents), and the halide attaches to the other carbon. Thus, the product is more stable.
Examples & Analogies
Think of this reaction like a couple deciding to sit next to each other at a table. If one side has more space (or options) than the other, they will choose to sit closer to the open side (the less substituted carbon), making it a more comfortable arrangement.
Halogenation
Chapter 2 of 2
π Unlock Audio Chapter
Sign up and enroll to access the full audio experience
Chapter Content
β’ Halogenation:
CHβ=CHβ + Brβ β CHβBrβCHβBr
Detailed Explanation
Halogenation involves the reaction of alkenes with halogens, like bromine (Brβ). When ethene reacts with bromine, it forms 1,2-dibromoethane (CHβBrβCHβBr). This reaction occurs through a mechanism that involves the formation of a cyclic intermediate, where the bromine atoms add across the double bond, resulting in a compound with two bromine substituents on adjacent carbons, showing a classic example of electrophilic addition.
Examples & Analogies
Imagine applying a two-sided sticker to a piece of paper (the alkene). As you press down, the sticker (bromine) adheres to both sides (the carbons on either side of the double bond). By using the two sides of the sticker, you effectively 'stick' them together at that location.
Key Concepts
-
Addition of HX: A method to convert alkenes to haloalkanes by adding hydrogen halides where the more stable product is favored.
-
Halogenation: The addition of diatomic halogens to alkenes produces vicinal dihaloalkanes, differing from Markovnikov's rule.
Examples & Applications
The reaction of ethylene (C2H4) with HBr results in bromoethane (C2H5Br), following Markovnikov's rule.
The reaction of ethylene (C2H4) with Br2 leads to 1,2-dibromoethane.
Memory Aids
Interactive tools to help you remember key concepts
Rhymes
When alkene does react, with HX itβll attract, a halide on the site, that's mostly white light.
Stories
A clever chemist named Mark was preparing to take a trip to the Halogen Valley. He always made certain to add HX first, in a way that ensured stability. On his journey to Halogenation Hill, he discovered the charming vicinal dihalo lands!
Memory Tools
For Markovnikov's rule: βMore Hs get Hβ, remember, more Hs win the game.
Acronyms
HABIT
for Hydrogen
for Alkene
for Bond
for Ideal addition
for Tetrahalides (for the bromination example).
Flash Cards
Glossary
- Haloalkanes
Organic compounds that contain one or more halogen atoms attached to an alkyl group.
- Alkenes
Hydrocarbons that contain at least one carbon-carbon double bond.
- Markovnikov's Rule
A principle that dictates the outcome of the addition of HX to alkenes, where the hydrogen atom adds to the carbon with more hydrogen atoms already attached.
- Halogenation
A chemical reaction involving the addition of halogens to an alkene, resulting in the formation of a dihaloalkane.
- Vicinal Dihaloalkane
A compound where two halogen atoms are attached to adjacent carbon atoms.
Reference links
Supplementary resources to enhance your learning experience.