ront: formation of epoxide

Back: MCPBA, attacks more electron filled double bond

Front: Acid-catalyzed opening of epoxides in water

1. Back: Acid (H⁺), Water (H₂O) (adds two OH groups on carbons)

Front: Acid-catalyzed opening of epoxides in alcohols

2. Back: Acid (H⁺), Alcohol (R—OH) (alkoxy group attacks more substituted side)

Front: Acid-catalyzed opening of epoxides using HBr, HCl or HI

3. Back: Br/I/Cl attacks more substituted side, stereoinversion

Front: Base-catalyzed opening of epoxides with alkoxides or hydroxide

4. Back: Alkoxy group bonds to less substituted side 

Front: Base-catalyzed opening of epoxides with organometallics

5. Back: R group binds to less substituted side

AROMATIC RINGS

Front: Electrophilic aromatic substitution: Halogenation

6. Back: Br₂, FeBr₃ (for bromination)

Front: Electrophilic aromatic substitution: Nitration

7. Back: HNO₃, H₂SO₄ (NO2 added

Front: Electrophilic aromatic substitution: Addition of amine to ring

Back: HNO3, H2SO4, Zn/HCl

Front: Electrophilic aromatic substitution: Sulfonation

8. Back: SO₃, H₂SO₄ (HSO3 added)

Front: Desulfonylation of benzene

Back: H2O, H+, heat 

Front: Electrophilic aromatic substitution: Iodination

Back: I2 and HNO3

Front: Friedel-Crafts Alkylation (adding alkyl group to benzene ring)

9. Back: Alkyl chloride (R—Cl), AlCl₃

Front: Friedel-Crafts Acylation (Adding carbonyl to benzene ring)

10. Back: Acyl chloride (RCOCl), AlCl₃/H2O

Front: Protonation of Alkenes: (Adding H to double bond and getting rid of double bond)

Back: HF will form cation, will attack aromatic ring

Front: Limitations of alkylation

Back: Rearrangements can occur and you can’t add something more than 2 carbons otherwise it will rearrange

Front: Clemmenson reaction

Back: Acyl chloride+ AlCl3, then add ZnHg to take off the carbonyl to make it a long alkane group

Front: Wolf Kishner reaction-

Back: NH2NH2, NaOH, takes off carbonyl and turns into alkane, same as clemmenson 

Front: Nucleophilic Aromatic Subsitution

Back: F>Cl>Br>I , Add nucleophile

Front: Hydrogenation of benzene ring

Back: 3H2, pressure, Pd

Front: Suzuki reaction adding alkene/aromatic/alkyl to aromatic ring

11. Back: Aryl halide, boronic acid, Pd catalyst

Front: Heck reaction- adding alkene to aromatic ring

12. Back: Aryl halide, alkene, Pd(OAc)₂, PPh₃, Et₃N less substituted side

Front: Grignard reaction with epoxides

13. Back: Grignard reagent (RMgX), epoxide

Front:Adding alkyl to aromatic ring or alkene 

Back: (R_2CuLi)+ R-X ( replaces leaving group)

Flashcard 1

Front: Addition of chlorine to benzene

Back: Reagent: Chlorine gas (Cl₂), Conditions: Heat and pressure or light, 

Flashcard 3

Front: Aromatic ring to ring with two double bonds 

Back: Reagents: Sodium (Na) or Lithium (Li) in liquid Ammonia (NH₃) (birch reaction)

Flashcard 4

Front: Side chain reaction: Alkylbenzenes to Alkylbenzenes

Back: Reagent: Zinc amalgam (Zn(Hg)) and Hydrochloric acid (HCl), Product: Alkylbenzene (Clemmenson reaction)

Flashcard 5

Front: Oxidation of an alkyl side chain on benzene to a carboxylic acid

Back: Reagent: Potassium permanganate (KMnO₄, hot and concentrated), Product: Carboxylic acid attached to benzene ring, everything is reduces thats carbon

Flashcard 6

Front: Halogenation of an alkyl side chain on benzene

Back: Reagent: Bromine (Br₂) with light (hv), Product: α-bromo alkylbenzene, adds two bromines on same carbon if there are two hydrogens

Flashcard 7

Front: Nucleophilic substitution at a benzylic position

Back: Reagent: Nucleophile (Nuc⁻), Conditions: Activated benzylic position, Product: Substituted alkylbenzene

Flashcard 8

Front: Oxidation of phenols to quinones

Back: Reagents: Sodium dichromate (Na₂Cr₂O₇) in sulfuric acid (H₂SO₄), Product: 2-chloro-1,4-benzoquinone

Front: Reducing nitro group on benzene ring to amine group

Back: Reagents: Zn, Sn, or Fe/ aq. HCl

Front: Taking HSO3 off ring

Back: H2O, H+/heat

Front: Protecting alcohol from grignard

Back: TIPS/ TBAF to take it off

ETHERS

Flashcard 1

Front: Synthesizes ethers from alcohols and halides

Back: Reagents: Alkoxide ion (R—O⁻) and primary alkyl halide (R'—X), where X = Cl, Br, I, OTs, etc. (Williamson Ether Synthesis)

Flashcard 2

Front: Synthesizes ethers via alkene addition

Back: Reagents: Alkene, Mercury(II) acetate (Hg(OAc)₂), alcohol followed by reduction with Sodium borohydride (NaBH₄) (Alkoxymercuration-Demercuration)

Flashcard 4

Front: Synthesizes phenyl ethers from phenols

Back: Reagents: Sodium hydroxide (NaOH) to form phenoxide ion, followed by reaction with an appropriate alkyl halide (not phenyl halides or tosylates)

Flashcard 5

Front: Cleaves ethers into alkyl halides 

Back: Reagents: Hydrogen halide (HX, where X = Br, I), in excess. R-O-R’ turns into R-X and R’-X, does not work on phenols so Ar-O-R turns into Ar-OH and R-X