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23 Jan 2026
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Comprehensive Benzene and Phenol Study Notes
joshhh
@josh0775
1 / 9
Benzene & Phenols
You're about to dive into one of chemistry's most fascinating molecular structures. Benzene might look simple with its ring of six carbons, but its behaviour is anything but ordinary.
This unit will show you why benzene defied chemists for years and how understanding its structure revolutionised organic chemistry. You'll also discover how adding just one -OH group creates phenol, dramatically changing the molecule's reactivity.
Quick Win: Master benzene's stability concept early - it's the key to understanding everything else in this topic!
Kekulé's Model and Benzene's Stability
Kekulé originally proposed benzene as cyclo-1,3,5-hexatriene with alternating single and double bonds. Three pieces of evidence proved this model wrong and revealed benzene's true nature.
Lack of reactivity was the first clue - benzene doesn't decolourise bromine water like alkenes do. If it really had C=C bonds, it would undergo addition reactions instantly.
X-ray diffraction showed all carbon-carbon bonds are identical in length, sitting perfectly between single and double bond lengths. Finally, hydrogenation enthalpies revealed benzene is 152 kJ/mol more stable than expected - this extra stability comes from delocalisation.
Exam Tip: Remember the three pieces of evidence against Kekulé's model - they're exam favourites!
Delocalised Structure Formation
Each carbon atom uses three electrons to bond with two carbons and one hydrogen, leaving one electron in a p-orbital perpendicular to the ring. These p-orbitals overlap above and below the carbon plane, creating regions of electron density.
This overlapping forms delocalised electrons that spread across all six carbons rather than being stuck between two atoms. It's this delocalisation that gives benzene its remarkable stability and unique properties.
Think of it like spreading risk across multiple investments - the electrons are more stable when shared across the entire ring rather than confined to specific bonds.
Nitration of Benzene
Benzene undergoes electrophilic substitution rather than addition, preserving its stable ring structure. For nitration, you need concentrated nitric acid, concentrated sulfuric acid catalyst, and temperatures around 50°C.
The first step creates the electrophile: HNO₃ + H₂SO₄ → HSO₄⁻ + NO₂⁺ + H₂O. The NO₂⁺ ion is your electrophile that attacks the benzene ring.
After the electrophilic attack and substitution occurs, the catalyst regenerates: HSO₄⁻ + H⁺ → H₂SO₄. This mechanism pattern repeats for other benzene reactions.
Memory Hook: "Nitration needs NO₂⁺" - remember the positive nitronium ion is your electrophile!
Halogenation of Benzene
Benzene won't react with bromine alone because its delocalised electrons don't create enough electron density to polarise Br₂. You need a halogen carrier like FeBr₃ to generate the electrophile.
Step 1 creates the electrophile: Br₂ + FeBr₃ → FeBr₄⁻ + Br⁺. The Br⁺ ion attacks the benzene ring, substituting for a hydrogen atom.
The final step regenerates your catalyst: H⁺ + FeBr₄⁻ → FeBr₃ + HBr. Without this catalyst, benzene and bromine simply won't react - that's how stable benzene really is.
Friedel-Crafts Reactions
Friedel-Crafts alkylation adds alkyl groups using alkyl chlorides and AlCl₃ catalyst. The mechanism starts by forming a carbocation: CH₃Cl + AlCl₃ → CH₃⁺ + AlCl₄⁻.
Friedel-Crafts acylation adds acyl groups using acyl chlorides. Step 1: CH₃COCl + AlCl₃ → CH₃CO⁺ + AlCl₄⁻. The acylium ion (CH₃CO⁺) then attacks the benzene ring.
Both reactions end with catalyst regeneration when H⁺ combines with AlCl₄⁻. These reactions are brilliant for building complex molecules from simple benzene rings.
Practical Note: Acylation is often preferred over alkylation because it avoids carbocation rearrangement problems!
Alkenes vs Arenes Reactivity
Alkenes have localised π-electrons that create sufficient electron density to polarise bromine molecules directly. They undergo electrophilic addition without needing catalysts.
Arenes (benzene compounds) have delocalised π-electrons spread across the ring, creating insufficient electron density for direct bromine polarisation. They need halogen carriers and undergo electrophilic substitution to maintain ring stability.
This difference explains why alkenes readily decolourise bromine water whilst benzene doesn't react at all. The delocalisation that makes benzene stable also makes it much less reactive than alkenes.
Phenol Structure and Bromination
Phenol contains a benzene ring with an -OH group attached, making it a weak acid with Ka = 10⁻¹⁰. The oxygen's lone pair electrons interact with the benzene ring, dramatically increasing its reactivity.
Phenol readily undergoes bromination with bromine water - no catalyst needed! The reaction produces 2,4,6-tribromophenol as a white precipitate: C₆H₅OH + 3Br₂ → C₆H₂Br₃OH + 3HBr.
This reaction decolourises bromine water and forms a distinctive white precipitate, making it perfect for identifying phenol in practicals.
Lab Alert: The tribromophenol precipitate is your visual confirmation that phenol is present!
Phenol vs Benzene Reactivity
Phenol is dramatically more reactive than benzene because the oxygen's lone pair electrons donate into the π-system, increasing electron density around the ring.
For nitration, phenol only needs dilute HNO₃ at room temperature, producing both 2-nitrophenol and 4-nitrophenol. Benzene requires concentrated acids and heating.
This increased reactivity means phenol undergoes electrophilic substitution much more readily. The -OH group is an activating group that makes the benzene ring electron-rich and reactive - the complete opposite of benzene's usual reluctance to react.
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Paul T
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The app is very easy to use and well designed. I have found everything I was looking for so far and have been able to learn a lot from the presentations! I will definitely use the app for a class assignment! And of course it also helps a lot as an inspiration.
Stefan S
iOS user
This app is really great. There are so many study notes and help [...]. My problem subject is French, for example, and the app has so many options for help. Thanks to this app, I have improved my French. I would recommend it to anyone.
Samantha Klich
Android user
Wow, I am really amazed. I just tried the app because I've seen it advertised many times and was absolutely stunned. This app is THE HELP you want for school and above all, it offers so many things, such as workouts and fact sheets, which have been VERY helpful to me personally.
Anna
iOS user
Best app on earth! no words because it’s too good
Thomas R
iOS user
Just amazing. Let's me revise 10x better, this app is a quick 10/10. I highly recommend it to anyone. I can watch and search for notes. I can save them in the subject folder. I can revise it any time when I come back. If you haven't tried this app, you're really missing out.
Basil
Android user
This app has made me feel so much more confident in my exam prep, not only through boosting my own self confidence through the features that allow you to connect with others and feel less alone, but also through the way the app itself is centred around making you feel better. It is easy to navigate, fun to use, and helpful to anyone struggling in absolutely any way.
David K
iOS user
The app's just great! All I have to do is enter the topic in the search bar and I get the response real fast. I don't have to watch 10 YouTube videos to understand something, so I'm saving my time. Highly recommended!
Sudenaz Ocak
Android user
In school I was really bad at maths but thanks to the app, I am doing better now. I am so grateful that you made the app.
Greenlight Bonnie
Android user
very reliable app to help and grow your ideas of Maths, English and other related topics in your works. please use this app if your struggling in areas, this app is key for that. wish I'd of done a review before. and it's also free so don't worry about that.
Rohan U
Android user
I know a lot of apps use fake accounts to boost their reviews but this app deserves it all. Originally I was getting 4 in my English exams and this time I got a grade 7. I didn’t even know about this app three days until the exam and it has helped A LOT. Please actually trust me and use it as I’m sure you too will see developments.
Xander S
iOS user
THE QUIZES AND FLASHCARDS ARE SO USEFUL AND I LOVE Knowunity AI. IT ALSO IS LITREALLY LIKE CHATGPT BUT SMARTER!! HELPED ME WITH MY MASCARA PROBLEMS TOO!! AS WELL AS MY REAL SUBJECTS ! DUHHH 😍😁😲🤑💗✨🎀😮
Elisha
iOS user
This apps acc the goat. I find revision so boring but this app makes it so easy to organize it all and then you can ask the freeeee ai to test yourself so good and you can easily upload your own stuff. highly recommend as someone taking mocks now
Paul T
iOS user
Comprehensive Benzene and Phenol Study Notes
joshhh
@josh0775
Ever wondered why benzene doesn't behave like other molecules with double bonds? This topic explores benzene's unique structure and how it undergoes completely different reactions compared to alkenes, plus how phenol takes benzene chemistry to the next level.
Benzene & Phenols
You're about to dive into one of chemistry's most fascinating molecular structures. Benzene might look simple with its ring of six carbons, but its behaviour is anything but ordinary.
This unit will show you why benzene defied chemists for years and how understanding its structure revolutionised organic chemistry. You'll also discover how adding just one -OH group creates phenol, dramatically changing the molecule's reactivity.
Quick Win: Master benzene's stability concept early - it's the key to understanding everything else in this topic!
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Kekulé's Model and Benzene's Stability
Kekulé originally proposed benzene as cyclo-1,3,5-hexatriene with alternating single and double bonds. Three pieces of evidence proved this model wrong and revealed benzene's true nature.
Lack of reactivity was the first clue - benzene doesn't decolourise bromine water like alkenes do. If it really had C=C bonds, it would undergo addition reactions instantly.
X-ray diffraction showed all carbon-carbon bonds are identical in length, sitting perfectly between single and double bond lengths. Finally, hydrogenation enthalpies revealed benzene is 152 kJ/mol more stable than expected - this extra stability comes from delocalisation.
Exam Tip: Remember the three pieces of evidence against Kekulé's model - they're exam favourites!
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Delocalised Structure Formation
Each carbon atom uses three electrons to bond with two carbons and one hydrogen, leaving one electron in a p-orbital perpendicular to the ring. These p-orbitals overlap above and below the carbon plane, creating regions of electron density.
This overlapping forms delocalised electrons that spread across all six carbons rather than being stuck between two atoms. It's this delocalisation that gives benzene its remarkable stability and unique properties.
Think of it like spreading risk across multiple investments - the electrons are more stable when shared across the entire ring rather than confined to specific bonds.
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Nitration of Benzene
Benzene undergoes electrophilic substitution rather than addition, preserving its stable ring structure. For nitration, you need concentrated nitric acid, concentrated sulfuric acid catalyst, and temperatures around 50°C.
The first step creates the electrophile: HNO₃ + H₂SO₄ → HSO₄⁻ + NO₂⁺ + H₂O. The NO₂⁺ ion is your electrophile that attacks the benzene ring.
After the electrophilic attack and substitution occurs, the catalyst regenerates: HSO₄⁻ + H⁺ → H₂SO₄. This mechanism pattern repeats for other benzene reactions.
Memory Hook: "Nitration needs NO₂⁺" - remember the positive nitronium ion is your electrophile!
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Halogenation of Benzene
Benzene won't react with bromine alone because its delocalised electrons don't create enough electron density to polarise Br₂. You need a halogen carrier like FeBr₃ to generate the electrophile.
Step 1 creates the electrophile: Br₂ + FeBr₃ → FeBr₄⁻ + Br⁺. The Br⁺ ion attacks the benzene ring, substituting for a hydrogen atom.
The final step regenerates your catalyst: H⁺ + FeBr₄⁻ → FeBr₃ + HBr. Without this catalyst, benzene and bromine simply won't react - that's how stable benzene really is.
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Friedel-Crafts Reactions
Friedel-Crafts alkylation adds alkyl groups using alkyl chlorides and AlCl₃ catalyst. The mechanism starts by forming a carbocation: CH₃Cl + AlCl₃ → CH₃⁺ + AlCl₄⁻.
Friedel-Crafts acylation adds acyl groups using acyl chlorides. Step 1: CH₃COCl + AlCl₃ → CH₃CO⁺ + AlCl₄⁻. The acylium ion (CH₃CO⁺) then attacks the benzene ring.
Both reactions end with catalyst regeneration when H⁺ combines with AlCl₄⁻. These reactions are brilliant for building complex molecules from simple benzene rings.
Practical Note: Acylation is often preferred over alkylation because it avoids carbocation rearrangement problems!
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Alkenes vs Arenes Reactivity
Alkenes have localised π-electrons that create sufficient electron density to polarise bromine molecules directly. They undergo electrophilic addition without needing catalysts.
Arenes (benzene compounds) have delocalised π-electrons spread across the ring, creating insufficient electron density for direct bromine polarisation. They need halogen carriers and undergo electrophilic substitution to maintain ring stability.
This difference explains why alkenes readily decolourise bromine water whilst benzene doesn't react at all. The delocalisation that makes benzene stable also makes it much less reactive than alkenes.
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Phenol Structure and Bromination
Phenol contains a benzene ring with an -OH group attached, making it a weak acid with Ka = 10⁻¹⁰. The oxygen's lone pair electrons interact with the benzene ring, dramatically increasing its reactivity.
Phenol readily undergoes bromination with bromine water - no catalyst needed! The reaction produces 2,4,6-tribromophenol as a white precipitate: C₆H₅OH + 3Br₂ → C₆H₂Br₃OH + 3HBr.
This reaction decolourises bromine water and forms a distinctive white precipitate, making it perfect for identifying phenol in practicals.
Lab Alert: The tribromophenol precipitate is your visual confirmation that phenol is present!
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Phenol vs Benzene Reactivity
Phenol is dramatically more reactive than benzene because the oxygen's lone pair electrons donate into the π-system, increasing electron density around the ring.
For nitration, phenol only needs dilute HNO₃ at room temperature, producing both 2-nitrophenol and 4-nitrophenol. Benzene requires concentrated acids and heating.
This increased reactivity means phenol undergoes electrophilic substitution much more readily. The -OH group is an activating group that makes the benzene ring electron-rich and reactive - the complete opposite of benzene's usual reluctance to react.
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The app is very easy to use and well designed. I have found everything I was looking for so far and have been able to learn a lot from the presentations! I will definitely use the app for a class assignment! And of course it also helps a lot as an inspiration.
Stefan S
iOS user
This app is really great. There are so many study notes and help [...]. My problem subject is French, for example, and the app has so many options for help. Thanks to this app, I have improved my French. I would recommend it to anyone.
Samantha Klich
Android user
Wow, I am really amazed. I just tried the app because I've seen it advertised many times and was absolutely stunned. This app is THE HELP you want for school and above all, it offers so many things, such as workouts and fact sheets, which have been VERY helpful to me personally.
Anna
iOS user
Best app on earth! no words because it’s too good
Thomas R
iOS user
Just amazing. Let's me revise 10x better, this app is a quick 10/10. I highly recommend it to anyone. I can watch and search for notes. I can save them in the subject folder. I can revise it any time when I come back. If you haven't tried this app, you're really missing out.
Basil
Android user
This app has made me feel so much more confident in my exam prep, not only through boosting my own self confidence through the features that allow you to connect with others and feel less alone, but also through the way the app itself is centred around making you feel better. It is easy to navigate, fun to use, and helpful to anyone struggling in absolutely any way.
David K
iOS user
The app's just great! All I have to do is enter the topic in the search bar and I get the response real fast. I don't have to watch 10 YouTube videos to understand something, so I'm saving my time. Highly recommended!
Sudenaz Ocak
Android user
In school I was really bad at maths but thanks to the app, I am doing better now. I am so grateful that you made the app.
Greenlight Bonnie
Android user
very reliable app to help and grow your ideas of Maths, English and other related topics in your works. please use this app if your struggling in areas, this app is key for that. wish I'd of done a review before. and it's also free so don't worry about that.
Rohan U
Android user
I know a lot of apps use fake accounts to boost their reviews but this app deserves it all. Originally I was getting 4 in my English exams and this time I got a grade 7. I didn’t even know about this app three days until the exam and it has helped A LOT. Please actually trust me and use it as I’m sure you too will see developments.
Xander S
iOS user
THE QUIZES AND FLASHCARDS ARE SO USEFUL AND I LOVE Knowunity AI. IT ALSO IS LITREALLY LIKE CHATGPT BUT SMARTER!! HELPED ME WITH MY MASCARA PROBLEMS TOO!! AS WELL AS MY REAL SUBJECTS ! DUHHH 😍😁😲🤑💗✨🎀😮
Elisha
iOS user
This apps acc the goat. I find revision so boring but this app makes it so easy to organize it all and then you can ask the freeeee ai to test yourself so good and you can easily upload your own stuff. highly recommend as someone taking mocks now
Paul T
iOS user
The app is very easy to use and well designed. I have found everything I was looking for so far and have been able to learn a lot from the presentations! I will definitely use the app for a class assignment! And of course it also helps a lot as an inspiration.
Stefan S
iOS user
This app is really great. There are so many study notes and help [...]. My problem subject is French, for example, and the app has so many options for help. Thanks to this app, I have improved my French. I would recommend it to anyone.
Samantha Klich
Android user
Wow, I am really amazed. I just tried the app because I've seen it advertised many times and was absolutely stunned. This app is THE HELP you want for school and above all, it offers so many things, such as workouts and fact sheets, which have been VERY helpful to me personally.
Anna
iOS user
Best app on earth! no words because it’s too good
Thomas R
iOS user
Just amazing. Let's me revise 10x better, this app is a quick 10/10. I highly recommend it to anyone. I can watch and search for notes. I can save them in the subject folder. I can revise it any time when I come back. If you haven't tried this app, you're really missing out.
Basil
Android user
This app has made me feel so much more confident in my exam prep, not only through boosting my own self confidence through the features that allow you to connect with others and feel less alone, but also through the way the app itself is centred around making you feel better. It is easy to navigate, fun to use, and helpful to anyone struggling in absolutely any way.
David K
iOS user
The app's just great! All I have to do is enter the topic in the search bar and I get the response real fast. I don't have to watch 10 YouTube videos to understand something, so I'm saving my time. Highly recommended!
Sudenaz Ocak
Android user
In school I was really bad at maths but thanks to the app, I am doing better now. I am so grateful that you made the app.
Greenlight Bonnie
Android user
very reliable app to help and grow your ideas of Maths, English and other related topics in your works. please use this app if your struggling in areas, this app is key for that. wish I'd of done a review before. and it's also free so don't worry about that.
Rohan U
Android user
I know a lot of apps use fake accounts to boost their reviews but this app deserves it all. Originally I was getting 4 in my English exams and this time I got a grade 7. I didn’t even know about this app three days until the exam and it has helped A LOT. Please actually trust me and use it as I’m sure you too will see developments.
Xander S
iOS user
THE QUIZES AND FLASHCARDS ARE SO USEFUL AND I LOVE Knowunity AI. IT ALSO IS LITREALLY LIKE CHATGPT BUT SMARTER!! HELPED ME WITH MY MASCARA PROBLEMS TOO!! AS WELL AS MY REAL SUBJECTS ! DUHHH 😍😁😲🤑💗✨🎀😮
Elisha
iOS user
This apps acc the goat. I find revision so boring but this app makes it so easy to organize it all and then you can ask the freeeee ai to test yourself so good and you can easily upload your own stuff. highly recommend as someone taking mocks now
Paul T
iOS user