Orgo 1 Reagents

BH₃·THF

• Base: Not a base (Lewis acid)

• Nucleophile: Not a nucleophile

• Bulky: No

• Solvent: No

• Purpose: Hydroboration oxidation of alkenes/alkynes #1, H2O2 and NaOH #2 (anti‑Markovnikov, syn addition)

Br₂

• Base: Not a base

• Nucleophile: N/A

• Bulky: N/A

• Solvent: N/A

• Purpose: 1) Halogenation of alkenes (anti addition via bromonium ion), CCl4 solvent. 2) Halohydrin, Br2 + H2O solvent, pi bond → alkyl halide. 3) Radical bromination. Br2 + hv (light) solvent, allylic would need NBS + ROOR.

Cl₂

• Base: N/A

• Nucleophile: N/A

• Bulky: N/A

• Solvent: N/A

• Purpose: Mostly halohydrin of alkenes (anti addition), free-radical halogenation (substitution with Cl2 + hv), alkyne halogenation w/ CCl4

DBN

• Base: Strong

• Nucleophile: Poor (non‑nucleophilic)

• Bulky: Yes

• Solvent: Not a solvent

• Purpose: E2 elimination (Hofmann product favored)

DBU

• Base: Strong

• Nucleophile: Poor

• Bulky: Yes

• Solvent: Not a solvent

• Purpose: E2 elimination for Hofmann, non‑nucleophilic base

DMS

• Base: Not a base

• Nucleophile: Weak

• Bulky: No

• Solvent: Polar aprotic

• Purpose: Reductive workup in ozonolysis (cleaves ozonide to carbonyls), step #2 in combo with O3

H₂

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: No

• Solvent: Not a solvent

• Purpose: Catalytic hydrogenation (alkenes/alkynes)

H₂O

• Base: Weak

• Nucleophile: Weak

• Bulky: No

• Solvent: Polar protic

• Purpose: Solvent, SN1/E1 favoring, hydration

H₂O₂

• Base: Weak

• Nucleophile: Weak

• Bulky: No

• Solvent: Polar protic

• Purpose: hydroboration oxidation of alkenes with NaOH (#2), #1 is BH3*THF

H₂SO₄

• Base: Not a base (strong acid)

• Nucleophile: Very weak

• Bulky: No

• Solvent: Polar protic

• Purpose: Acid‑catalyzed hydration, dehydration (E1)

H₃O⁺

• Base: Not a base

• Nucleophile: Very weak

• Bulky: No

• Solvent: Polar protic

• Purpose: acid catalyzed hydration

Hg(OAc)₂

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: No

• Solvent: Not a solvent

• Purpose: Oxymercuration (Markovnikov hydration without rearrangement)

HgSO₄

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: No

• Solvent: Not a solvent

• Purpose: Step #2 in Alkyne hydration (Markovnikov → ketone) with ketone-enol tautomerization, step #1 = H2SO4 + H2O

I₂

• Base: Not a base

• Nucleophile: Weak

• Bulky: No

• Solvent: Not a solvent

• Purpose: Halogenation, iodoform reactions

KMnO₄

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: No

• Solvent: Polar protic (often basic aqueous)

• Purpose: Strong syn dihydroxylation w/ NaOH of alkene to alkane + 2 OH cis (alkenes → diols or cleavage)

KOt‑Bu

• Base: Strong

• Nucleophile: Poor

• Bulky: Yes

• Solvent: Polar aprotic (often t‑BuOH present)

• Purpose: E2 elimination (Hofmann product)

Lindlar’s Catalyst

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: N/A

• Solvent: Not a solvent

• Purpose: Partial hydrogenation of alkynes → cis‑alkenes

mCPBA

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: Moderately

• Solvent: Not a solvent

• Purpose: Epoxidation of alkenes

Na

• Base: Very strong (via NaNH₂ or Na/NH₃)

• Nucleophile: Not a nucleophile

• Bulky: No

• Solvent: Not a solvent

• Purpose: Liquid metal used in dissolving metal reductions as step #1, step #2 is NH2, RADICAL mechanism

NaBH₄

• Base: Weak

• Nucleophile: Hydride donor

• Bulky: No

• Solvent: Polar protic (MeOH, EtOH)

• Purpose: step #2 of oxymercuration-demercuration with step #1 being Hg(OAc)2, H2O

NaH

• Base: Very strong

• Nucleophile: Weak

• Bulky: No

• Solvent: N/A

• Purpose: Deprotonation of alcohols/amines (forms alkoxides, enolates)

NaHSO₃

• Base: Weak

• Nucleophile: Weak

• Bulky: No

• Solvent: Polar protic

• Purpose: OsO4 step #1, step #2 bisulfite addition for SYN dihydroxylation

NaNH₂

• Base: Very strong

• Nucleophile: Strong

• Bulky: No

• Solvent: Liquid NH₃ (polar protic‑like)

• Purpose: Deprotonation, alkyne alkylation

NaOH

• Base: Strong

• Nucleophile: Strong

• Bulky: No

• Solvent: Polar protic

• Purpose: SN2, E2 for Zaitsev product, hydrolysis with H2O?

NaOMe

• Base: Strong

• Nucleophile: Strong

• Bulky: No

• Solvent: Polar protic (MeOH)

• Purpose: SN2, E2 reactions for Zaitsev

NBS

• Base: Not a base

• Nucleophile: Weak

• Bulky: No

• Solvent: Not a solvent

• Purpose: Allylic/benzylic bromination (radical)

NH₃ (l)

• Base: Weak–moderate

• Nucleophile: Moderate

• Bulky: No

• Solvent: Polar protic

• Purpose: SN2 substitutions, dissolving metal reactions in LIQUID form specifically with Na metal

Ni

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: N/A

• Solvent: Not a solvent

• Purpose: Hydrogenation catalyst

NMO

• Base: Weak

• Nucleophile: Weak

• Bulky: No

• Solvent: Polar aprotic

• Purpose: Co‑oxidant for OsO₄ (syn dihydroxylation)

O₃

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: No

• Solvent: Not a solvent

• Purpose: Ozonolysis of alkenes

OsO₄

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: No

• Solvent: Not a solvent

• Purpose: Syn dihydroxylation of alkenes

Pd/C

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: N/A

• Solvent: Not a solvent

• Purpose: Catalytic hydrogenation, one of the catalyst options

Pt/C

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: N/A

• Solvent: Not a solvent

• Purpose: Catalytic hydrogenation

Pyridine

• Base: Weak

• Nucleophile: Weak

• Bulky: Moderately

• Solvent: Polar aprotic

• Purpose: In conjunction in step #1 for OH leaving group conversion (TsCl reactions), #2 depends (typically either bulky base or NaOMe/OEt)

TsCl

• Base: Not a base

• Nucleophile: Not a nucleophile

• Bulky: Yes

• Solvent: Not a solvent

• Purpose: Converts alcohols to tosylates (good leaving groups)

9‑BBN

• Base: Not a base (Lewis acid)

• Nucleophile: Not a nucleophile

• Bulky: Yes

• Solvent: N/A

• Purpose: Selective hydroboration (anti‑Markovnikov), used to replace BH3 for higher selectivity of anti-markov addition, but otherwise same purpose