Topic 12 Organic compounds containing oxygen and nitrogen Presentation

Hydroxy Vibes

Alcohols 🍹

  • Functional Group: So, you got that -OH squad, and they’re the life of the organic party because they bring all the fun! This hydroxyl group makes alcohols unique and gives them mad reactivity. 🦄🚀

  • Naming: When you see ‘-ol’ at the end of a name, you know we’re talking about alcohols! It’s like their signature look, giving you a heads up that they’re ready to mix and shake things up.

  • General Formula: The formula CnH2n+1OH is how we break down alcohols; it tells you how many carbon atoms are in the squad and how the hydrogen and oxygen fit into the vibe check. 🌟

  • Examples: Think Methanol (CH3OH) as the OG baby drink, and then we roll into Propan-2-ol (a.k.a isopropyl alcohol) and Butan-1,3-diol as your party essentials—these are versatile and ready to flow! 🎉

Structures 💎

  • Propan-2-ol: Who’s chillin’ as H3C-CH(OH)-CH3? That’s right, it’s your go-to alcohol ready to get the party started!

  • Butan-1,3-diol: Keep it fancy with H3C-CH(OH)-CH2-CH(OH)-CH3. With two -OH groups, it’s like the social butterfly of the alcohol world!

Types of Alcohols 👑

  • Primary (1º): This one is the solo artist of alcohols; it has the OH group on a carbon that’s only hanging out with one other carbon friend. Think of it like your classic indie vibe!

  • Secondary (2º): Here’s where the party expands! The OH is on a carbon connected to two others, making this alcohol versatile and ready for a good time.

  • Tertiary (3º): This is the superstar of alcohols, with the OH on a carbon that’s living large, surrounded by three other carbons. They don’t often oxidize, keeping their glow! 🌟

Alcohol Properties 🔥

  • Flammability: These drinks are super flammable! Like, if they catch a spark, it’s full-on bonfire mode! 🔥💥

  • Hydrogen Bonding: They’re bonding like besties at a concert, giving them higher boiling points than normal alkanes. That’s why ethanol (alcohol) boils at 78.3°C while ethane (not an alcohol) is chilling at -89°C! 🍹🔥

Water Business 🌊

  • Short-Chain Alcohols: These guys are your water-friendly homies, mixing well like friends at a pool party thanks to their -OH group forming hydrogen bonds with water!

  • Long-Chain Alcohols: As we go longer, it’s less chill. They start to act more hydrophobic, like a swimmer who just can’t hang at the party anymore! 😅

Reactions ⬆

  • Nucleophilic Substitution: When the -OH gets swapped out for something spicier, like a halogen! It’s like the ultimate glow-up for alcohols. 🦄🔥

    • Example Reactions:

      • HBr + C2H5OH → C2H5Br + H2O, where ethanol just got a glow-up from hydrogen bromide...

      • PCl5 + C2H5OH → C2H5Cl + HCl + POCl3, turning the ethanol into something new and exciting with phosphorus pentachloride!

  • Oxidation: Alcohols are on a transformative journey! 🍃

    • Primary Alcohols: They can start as alcohol, oxidize into an aldehyde, and keep going all the way to becoming carboxylic acids! Transformative vibes!

    • Secondary Alcohols: These change into ketones, getting a new identity.

    • Tertiary Alcohols: Not as easy to change, these keep their cool and don’t oxidize as easily!

    • Common Oxidizing Agents: Acidified potassium dichromate (K2Cr2O7/H2SO4) is the go-to for making these changes happen!

    • Example: Take ethanol (a 1º alcohol) and it can be oxidized to ethanal (an aldehyde) in a sleek move! All that is needed is to break that C-C bond—think of it as a party breakup!

  • Dehydration to Alkenes: This is a dramatic exit where alcohols lose water and become alkenes, totally transformed! A lil acid (like H2SO4) kicks off this reaction!

    • Example: C2H5OH → Ethylene (C2H4) + H2O; just like shedding tears but coming out looking fresh!

    • Curly Arrow:

      • Step 1: Protonation CH₃-CH₂-OH + H⁺ → CH₃-CH₂-OH₂⁺ Step 2: Loss of Water CH₃-CH₂-OH₂⁺ → CH₃-CH₂⁺ + H₂O Step 3: Formation of Alkene CH₃-CH₂⁺ → CH₂=CH₂ + H⁺

  • Esterification: Where the magic happens! 🔮 This is when you mix an alcohol with a carboxylic acid, and what do you get? Esters!

    • Example: Butan-1-ol + Ethanoic acid → Butyl ethanoate + H2O. It’s like cocktails of organic chemistry! 🍸

Triiodomethane Test (Iodoform Test) 🧪

  • What It Tests For: This test is used to identify secondary alcohols (2º) with the structure R-CH(OH)-CH3 or methyl ketones (R-CO-CH3). It’s like a chemistry detective sniffing out specific groups! 🕵‍♂️

  • Reagents: Iodine (I₂) and sodium hydroxide (NaOH) solution. These are the key players in the reaction. 🧂

  • How It Works:

    1. The secondary alcohol or methyl ketone reacts with iodine (I₂) and sodium hydroxide (NaOH).

    2. If the R-CH(OH)-CH3 or R-CO-CH3 group is present, a pale yellow precipitate of triiodomethane (CHI₃) forms. This is the telltale sign of a positive result! 💛

  • Positive Result: A pale yellow precipitate of triiodomethane (CHI₃) forms. It’s like the chemistry version of a mic drop! 🎤💥

Phenols 🍷

Structure

  • Definition: These are like the queen bees of the organic world, featuring an -OH attached to a benzene ring. They give off sophisticated vibes. ✨🌹

  • Example Molecules: Paracetamol is like the go-to for headaches, and 3,5-dimethyl phenol is all about that ol’^ school cool energy!

Phenol Reactions – The Drama 🎭

  1. Bromine Water + Phenol: The Brainrot Breakdown 🧠💥

    1. Bromine Water: It’s out here looking like Fanta 🍊—vibing in its orange/brown era.

    2. Phenol: Phenol walks in like, “I’m the main character.” 💅 It sees bromine water and goes, “Let’s make this ✨spicy✨.”

    3. The Reaction:

      • Bromine water’s like, “I’m orange, I’m iconic—”

      • Phenol interrupts: “NOT ANYMORE, SIS.” 🚫

      • The orange/brown colour YEETS itself out of existence. 🏃‍♂💨

      • Meanwhile, a white precipitate (2,4,6-tribromophenol) forms like, “Hey besties, I’m here now!” 👋

    4. Final Vibes:

      • The solution goes from Fanta 🍊 to crystal clear 💧 with a white snowglobe moment ❄ at the bottom.

  2. Iron(III) Chloride Test:

    • Phenol meets FeCl₃, and it’s a glow-up moment. 💜

    • The mix turns red/purple—like a TikTok filter but in real life. 🎨

    • Salicylic acid (with its phenol group) also gets in on this trend.

Alcohols and Phenols – Weak Acids Vibes 🍋

  • Alcohols and Phenols: These baddies can donate protons (H⁺), but they’re not the main characters—just supporting acts. 💁‍♀

    • The tea:

      ROH⇌RO−+H+ROH⇌RO−+H+

    • Acidity ranking: Carboxylic acids > Phenols > Alcohols.

      • Carboxylic acids are the queens 👑 (resonance-stabilized negative ions).

      • Phenols are the vibey middle child 🌸 (aromatic ring helps a bit).

      • Alcohols are the babies 👶 (no resonance, just chillin’).

Amines 🤖

  1. Types

    • Primary Amines (R-NH2): Here's the solo artist! Just one carbon hanging out, living the life.

    • Secondary Amines (R-N(R')H): It’s got a duo vibe—nutin’ like two carbon buddies in the mix!

    • Tertiary Amines (R-N(R')(R’)): Bringing the crowd with three carbons, these are the party animals of the amine family, taking charge!

  2. Basic Properties:

    • Amines are out here flexing their lone pair of electrons on the N-atom. 😎

    • This lone pair is like, “I’m single and ready to mingle!” 💃

    • It can accept a proton (H⁺) from acids, making amines basic.

    • Basically, amines are the chemistry version of that friend who’s always down to help. 🙌

  3. Amine Salt Formation:

    • When amines meet an acid, it’s a glow-up moment. ✨

    • The amine’s lone pair grabs a proton (H⁺) from the acid, and they form an amine salt.

    • Reaction:

      R-NH₂+HCl→R-NH₃⁺Cl⁻R-NH₂+HCl→R-NH₃⁺Cl⁻

      (Amine + Hydrochloric Acid → Amine Salt)

    • The amine salt is like, “I’m iconic now.” 💅

  4. Formation of Amines from Primary Haloalkanes:

    • Amines can be formed from primary haloalkanes via an SN2 reaction.

    • The haloalkane is like, “I’m leaving, bye!” 👋

    • The amine (e.g., ammonia, NH₃) is like, “I’m taking your spot, bestie.” 💃

    • Curly Arrow Mechanism:

      • The lone pair on the N-atom attacks the carbon attached to the halogen.

      • The halogen leaves, taking its electrons with it.

      • Reaction:

        R-X+NH₃→R-NH₃⁺X⁻→R-NH₂+HXR-X+NH₃→R-NH₃⁺X⁻→R-NH₂+HX

        (Haloalkane + Ammonia → Amine + Hydrogen Halide)

Amides – The Brainrot Breakdown 🧠💥

  1. Amides: These are the cool kids of organic chemistry. They’ve got that R-C(O)NH₂ vibe, mixing carbonyl (C=O) and amine (NH₂) energy into one iconic package. 💅✨

  2. Formation of Amides from Esters and Excess Amine:

    • Esters are like, “I’m fancy, but I’m ready to change.” 🍷

    • Amines are like, “I’ve got excess energy, let’s make something iconic.” 💃

    • When esters meet excess amine, it’s a glow-up moment. ✨

    • The amine attacks the carbonyl carbon of the ester, kicking out the -OR group (like, “Bye, Felicia!” 👋).

    • The result? An amide and an alcohol as a byproduct.

    • Reaction:

      R-COOR’+NH₃→R-CONH₂+R’-OHR-COOR’+NH₃→R-CONH₂+R’-OH

      (Ester + Excess Amine → Amide + Alcohol)

Vocabulary 🔎

  • Bronsted Acid: Proton donor (giving away protons like candy! 🍬).

  • Bronsted Base: Proton receiver (always ready to catch and roll 🙌).

  • Decomposing: Breaking it all down—post-party cleanup! 🎉🧹

  • Flammable: Goes up in flames—handle with care! 🔥

  • Miscible: Liquids that vibe well together. 🥂