1. Reactions for Exam (you will have the reducing agent chart on exam): Everything from 241a (epoxidations, halides from alcohols, ether synthesis) Electrophilic substitution reactions: bromination & chlorination* iodination nitration* sulfonation* Friedel Craft alkylation* & acylation* Diazonium formation* & reactions with halides, BF 4 -, water, alcohols, electron rich arenes, hypophosphorous acid Nucleophilic aromatic substitution (electron deficient arenes with leaving group)* Benzyne formation and reaction as electrophile or diene in DA reaction* Reduction of acyl to alkyl group (Clemmensen or Wolff Kishner reductions) Reduction of nitro to amine & oxidation back Desulfonation with heat Reaction of arene sulfonic acid with NaOH to phenol KMnO 4 oxidation of alkyl groups with benzylic protons to CO2H Formation and reaction of aryl Grignards (with carbonyl to give alcohols) Hydroboration oxidation* & Oxymercuration-demercuration Halohydrin formation & conversion to epoxides* Ring opening (acid or base) of epoxides* Oxidation of alkenes to diols Acetylation of aniline or phenol*

2. Reactions for Exam 3 continued: Free radical chemistry of benzylic groups (bromination, chlorination) Conversion of alcohol hydroxide to halide (SOX 2 or PX 3 ) with inversion (extra credit mech) Conversion of alcohol hydroxide to tosylate with retention* Protection & deprotection of hydroxyl group with trimethylsilyl group Williamson synthesis of ethers (including cyclic ethers)* mCPBA formation of epoxides (extra credit mech) Oxidation of alcohols to aldehydes or ketones Oxidation of alcohols to carboxylic acids Formation of alcohols from aldehydes or ketones (NaBH 4 ) Formation of alcohols from carboxylic acids or esters (LiAlH 4 or BH 3 ) Reaction of Grignards to aldehydes, ketones or esters to give alcohols. Acetal formation from aldehydes and ketones* Hemiacetal formation from hydroxyaldehydes or hydroxyketones* Imine formation from aldehydes or ketones with primary amines* Enamine formation from aldehydes or ketones with secondary amines* Hydrate formation from aldehydes or ketones* Cyanohydrin formation aldehydes or ketones* And hydrolysis of the above* Wittig reaction of aldehydes and ketones to afford alkenes* (includes synthesis of Wittig reagents from alkyl halides)

3. Reactions for Exam 3 continued: Formation of carboxylic acid from organolithium or Grignard reacting with carbon dioxide* Formation of carboxylic acid from hydrolysis of nitriles. * Formation of nitriles by SN2 substitution on primary halides or tosylates.* Formation of acid chloride from carboxylic acid with SOCl2 (extra credit mech) Reaction of acid chloride with alcohol to give ester* Reaction of acid chloride with amine to give amide* Reaction of acid chloride with cuprate to give ketone Reaction of acid chloride with organolithium or Grignard to give tertiary alcohol (extra credit mech) Acetylation of amines and alcohols with acetic anhydride to give acetamides and acetyl esters.* Acid catalyzed formation and hydrolysis of esters.* Base catalyzed hydrolysis of esters.* Reaction of esters with organolithium or Grignards (2 equivalents) to afford 3° alcohols DCC synthesis of esters from alcohols and carboxylic acids (extra credit mech) DCC synthesis of amides from amines and carboxylic acids (extra credit mech) Dehydration of primary amides to nitriles SN2 reaction of carboxylate salts with primary halides or tosylates to give esters.*

4. 1,4 addition of cuprates to enones. 1,2 addition of organolithium or Grignards to enones. Diborane or organoborane reduction of carboxylic acids to 1° alcohols. (extra credit mech) Reaction of organolithium or Grignards to epoxides. Reaction of nitriles with organolithium or Grignards to afford ketones. (extra credit mech) Acid or base catalyzed hydrolysis of amides to carboxylic acids.* Acid or base catalyzed tautomerization of ketones, amides, etc.* Base formation of kinetic enolate with LDA (low temp, polar aprotic solvent)* Base formation of thermodynamic enolate with alkoxide base (Room temp, polar protic solvent)* Alpha halogenation of enolates* Alpha alkylation of enolates* Acid catalyzed alpha halogenation* Iodoform reaction* Beta elimination of alpha halogenated carbonyl to give a, b unsaturated carbonyl* Malonic ester synthesis (extra credit mech) Acetoacetic ester synthesis (extra credit mech)