reagents

KOtBu (potassium ter-butoxide)

Strong, not nucleophilic (bulky), FAVORS E2

Alkoxides - RO^- (CH3O-, CH3CH2O-,…) tert-butoxide

Strong base and nucleophile, with primary = SN2, secondary = SN2 or E2, tertiary = E2. tert-bitoxide favors E2 cuz bulky

NaH, sodium hydride

very strong base, not a nucleophile, williamson ether synthesis, and used for deprotonation reactions. gets rid of H so ether can be formed

DBU/DBN

strong, sterically hindered, FAVORS E2

Which reagents favor E2?

DBU/DBN/KOtBu

NaNH2- sodium amide (2)

very strong base, can be nucleophilic, mainly used for E2 can undergo TWO eliminations so it can remove from vinyl halide or alkyl halides, making it useful in deprotonation and synthesis reactions. make alkyne then deprotanate

SOCl2- Thionyl chloride

A reagent used to convert alcohols into chlorides, often employed in the synthesis of alkyl chlorides from alcohols. (OH —> Cl) with pyridine leads to inversion

PBr3 - potassium tribromide

alcohols into alkyl bromide, primary and secondary alcohols through SN2 (OH —> Br) with INVERSION

POCl3

alcohol into alkene WITH pyridine, dehydration, E2, and formation of alkenes through elimination reactions.

Pyridine

weak base, used with POCl3=alkene, SOCl2=alkyl chloride, and TsCl=tosylate,

H2SO4

strong acid that protonates alcohols usually for E1, leading to the formation of alkenes through dehydration reactions.

as heat increases which reaction is favored

the elimination reaction is favored

ZnCl2

lewis acid, usually paired with HCl to convert alcohols into alkyl chlorides, teritary = Sn1,

TsOH

strong acid, used for dehydration, allowing the elimination of water to form alkenes. It is commonly used in organic synthesis to convert alcohols into alkenes through E1 mechanisms. (like H2SO4)

TsCl (tosyl)

OH into OTs, a sulfonate ester that can be used as a better leaving group in nucleophilic substitutions and eliminations.

DMSO

polar aprotic solvent, supports SN2 reactions by stabilizing the transition state and not solvating the nucleophile. (strong base can cause E2)

HMPA

polar aprotic, supports SN2, increases nucleophilicity and solvates cations.

DMF

polar aprotic, SN2, anions can react well

THF

Aprotic ether, used with strong bases, not as polar

HCN

weak acid, donates hydrogen ions. favor SN2, add a carbon

Acetic acid CH3COOH

polar protic solvent, supports SN1 and E1 by stabilizing carbocations and hydrogen bonding.

N3

strong nucleophile, weak base, favors SN2,