#enol

Enol walked the hallways of his home with heavy steps. Today was the day where the would all be classified into classrooms depending on their singularities. Why did he dRead this, you ask? You see, the thing is that no one knows what Enol's singularity is: none of the doctors, teachers, or classmates know what it is. He knows, though

He arrived at his room's mailbox, and opened the letter. Why the formalities? Why couldn't they just tell them what class to go to? Whatever They assigned him to a special classroom, of course. Why wouldn't they? You can't strenghten your singularity if you don't even know what it is or what to do to make it stronger. Not that he wanted to make it stronger

He wondered if there would be someone else at his class. Probably not

With a sigh, he went to the main hall that separated the wards, and skipped them, going for the small but new class. He opened the door to find a completely normal-looking class, except that it was lacking the students and teachers. Was he really going to spend the rest of his school life like this? It's not like he had a choice, anyways

All of a sudden, a door opened

"Oh! Hi Enel! I didn't expect to see you here- If I'm, I don't know where I expected you to be, since you have no singularity and all. Ah- sorry. Does that offend you?"

Bianca. That stupid little popular girl everyone seemed to love for some reason. There wasn't anyone in the facility who didn't like her (except Enol, of course) and yet, every time she opened her mouth, the urge to punch her in the face so she'd shut up became stronger. What was she even doing here? True, no one outside of the teachers and researchers knew what her singularity was, but why send her here? Surely there was a more appropriate classroom for her, right? To be honest, Bianca had always stuck out like a sore thumb in Enol's memories. Not just because of her albinism, but because of her apparent immunity to his singularity

You see, Enol could read minds, wether he wanted to or not. There's wasn't an off button, so he'd have to listen to someone talk and think at the same time, and figure out which one was which. The noise was too much, so he decided not to be with people at all. But Bianca... he had never read her thoughts. Maybe she was a robot. Maybe. He could actually see the people at the facility pulling something like that out

She sat next to him. "So? What's up?"

He gave her the same answer he had given to countless people before: silence

Still, she didn't give up. "Oh, right, you're not much of a talker, are ya?"

Silence

First Semester of Organic Chemistry

Radical Halogenation - [x] [x] [x]

Initiation // Propagation // Termination

Substitution Nucleophilic Reactions - [x] [x] [x]* [x]

Walden Inversion // “umbrella flip” that occurs with SN2 reactions No stereospecificity in SN1 reactions Watch out for hydride shifts and degree of carbocations Solvolysis // solvent is the nucleophile Electrophile // Nucleophile // Leaving Group // Solvent

Elimination Reactions/Dehydrohalogenation - [x] [x] [x] [x]

Zaitsev’s Rule // non-bulky base favors more sub. alkene Hoffmann’s Rule // bulky base removes less-hindered protons Beta Hydrogens // anti to leaving group

*Contains information for radical halogenation, SN and E reactions

Alkene Reactions - [x]

Syn // same side Anti // opposite side Hydrogenation Palladium // catalyst of platinum on carbon  Markovnikov’s Rule // regiospecific to the more sub. carbon Acid-Catalyzed Hydration - [x] Hydrofluoric Acid // not a strong enough acid for this reaction Kinetic Product // Thermodynamic Product Oxymercuration Mercury // allows no rearrangement  Hydroboration Ozonolysis - [x] 

Alkene Practice Problems - [x] [x] Alkene Roadmap

Alkyne Reactions - [x]

Hydrogenation  Lindlar’s Catalyst // alkyne to alkene only! Hydration Alkylation of Acetylides - [x] Double Dehydrohalogenation

Alkyne Practice Problems - [x] [x] [x] Alkyne Roadmap

Alcohol Reactions - [x]

Primary // Seondary // Tertiary  Sodium Borohydride // doesn’t work with esters Lithium Alummunum Hydride // more reactive and does work with esters

Alcohol Practice Problems - [x] [x] [x]* *Also contains epoxide practice problems! Alcohol Roadmap

Epoxide Reactions - [x]

Pretty straightforward reactions Weak Nucleophile // more sub. side Strong Nucleophile // less hindered side

Epoxide Practice Problems - [x] Epoxide Roadmap

Second Semester of Organic Chemistry

Ether Reactions - [x]

Reaction with HX Breaks the bond at the oxygen connection to form two alkyl halides Williamson Ether Synthesis - [x] Alkoxy Mercuration Demeruration

Sulfide Reactions - [x]

Diels-Alder Reactions - [x] [x] [x]

Diene // nucleophilic with an electron donating group Dienophile // electrophilic with an electron withdrawing group Watch out for regiochemistry and endo product is preferred

Electrophilic Aromatic Substitution - [x] [x] [x]

Halogenation Halogens are deactivators but ortho/para directors Alkylation Rearrangement // a 2+ carbon chain can undergo rearrangement for a more stable carbocation Limitation // installing one alkyl group is difficult due to a reactive ring Acylation Clemmensen Reduction // removes the carbonyl and is preferred to overcome rearrangement Limitations // 1) unable to install more than one acyl group because the ring becomes less reactive 2) no reaction if the ring has a nitro group present Sulfonation Can be used to make ortho position more active Nitration Reduction Reaction // converts the nitro group into an amine Carboxylic Group Addition Gatterman-Koch Reaction The addition of an aldehyde, not a ketone!

Nucleophilic Aromatic Substitution - [x] [x]

Criteria // 1) must have strong electron withdrawing group 2) must contain an LG 3) the LG must be ortho or para to the electron withdrawing group Addition-Elimination Meisenheimer Complex // the intermediate where the negative charge is being shifted around the ring for stability Reservoir // negative charge is pushed onto an atom when the ring gets attacked by a nucleophile Halogens // F > Cl > Br > I, due to bond length and electron density Elimination-Addition - [x] Benzyne // funky intermediate where a triple bond is located on the ring

**Please note that I won’t go into detail about activators versus deactivators.

Aldehyde and Ketone Reactions - [x] [x] [x]

Oxygen Nucleophiles Dean-Stark // removal of water to create the two ethers Diol // forms a cyclic acetal  Hydration // addition of two -OH groups Sulfur Nucleophiles Raney Ni // neutral conditions Thiols // react similar to diols  Clemmensen // acidic conditions Nitrogen Nucleophiles Preparation // jones reagent, PCC, ozonolysis Imine // primary amine that forms a double bond between N - C Enamine // secondary amine  Oxime // the nitrogen is bonded to an -OH group Hydrazone // the nitrogen is bonded to another amine group Wolff-Kishner Reduction // basic conditions Carbon Nucleophiles Grignard Reagent - [x] // Wittig Reagent - [x] Addition of CN Oxidation of Aldehydes Tollen’s Test // works in the presence of aldehydes  Acid Chlorides 

Amine Reactions - [x] [x]

Synthesis of Amines - [x] [x] SN2 Reaction // alkylation of ammonia and doesn’t stop at mono- Reductive Amination // formation of an amine from a carbonyl  Gabriel Synthesis Note // only works with primary amines Acylation of Amines Acids Hoffmann Rearrangement Nitrene // Isocyanate Hoffmann Elimination Also, forms a terminal alkene in the process Nitrosation - [x] In Situ // formation that immediately react with the amine before anything happens Sandmayer Reaction Aromatic Diazonium Salts // CuCl, CuBr, CuCN...

Carboxylic Acid and Derivative Reactions - [x] [x] [x] [x]

Golden Rule // never expel H or C Proton Transfer // may or may not occue Fisher-Sterification - [x] Amides from Carboxylic Acids Acid Halides Water // Alcohol // Amine // LAH // RMgX // R2CuLi Acid Chlorides Water // forms a carboxylic acid Alcohol // forms an ester Formation of Anhydrides - [x] Ester Synthesis Hydrolysis // acidic conditions in water Saponification // basic conditions in water Alcoholysis // formation of a new ester from another ester Reaction with RM // adds R group twice Reaction with Hydride // adds H twice Aminolysis Reaction of Amides Hydrolysis // Alcoholysis // Aminolysis Synthesis of Dicarboxylic Acids - [x] Polycarbonates - [x] Polyurethanes Ring Opening Polymerization - [x] Remember // Acid Halides > Anhydrides > Esters > Amides Can only travel from left to right in synthesis

Enol and Enolate Reactions  - [x] [x]

Aldol Condensation - [x] Ketones // yields are small Crossed Aldol - [x] Note // watch out what product needs to be formed, the compound being added dropwise is important Alpha Halogenation Haloform Reaction Iodoform Reaction Hell-Volhard-Zelinsky Reaction - [x] Claisen Condensation - [x] Acetoacetic Ester Synthesis - [x] Malonic Ester Synthesis - [x] Conjugate Addition Robinson Annulation Kinetic Enolates

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