orgo reagents

HCl

Properties: strong acid, Cl- nucleophile

Uses: Protonates alcohols, converts ROH → RCl

H₂SO₄

Properties: Strong acid, Dehydrating

Uses: Hydration of alkenes → alcohols; acid-catalyzed reactions, adds to more substituted carbon

H₃PO₄

Properties: Strong Acid, Non-nucleophilic

Uses: safer alternative to H₂SO₄ for dehydration of alcohols

HBr

Properties: Strong Acid, Br- Nucleophile

Uses: converts alcohols → alkyl bromides

HI

Properties: Strong Acid, Strongest of the H-X acids where X = halide

Uses: cleaves ethers; converts ROH → RI

Acetic Acid (CH₃COOH)

Properties: Weak Acid

Uses: Mild acidic conditions

Phenol

Properties: Weak Acid

Uses: Acid-Base Comparisons

H₂O

Properties: Very weak acid/base, Good Leaving Group

Uses: Solvent, hydrolysis

NaOH & KOH

Properties: Strong Base

Uses: E2 eliminations and SN2 reactions

NaOCH₃ & NaOEt

Properties: Strong Base, Small

Uses: Favors E2 or SN2

t-BuOk

Properties: Strong but Bulky Base

Uses: E2 → Hofmann Alkene (less substituted and less stable)

NaOH

Properties: Very Strong Base

Uses: Deprotonates alcohols

NH₃ & Amines

Properties: Weak Base

Uses: Acid-Base Reactions

Br₂ + hv

Properties: Radical Halogenation

Uses: Substitutes H with Halogen, More selective

Cl₂ + hv

Properties: Radical Halogenation

Uses: Substitutes H with halogen

NBS + hv

Properties: Allylic Bromination

Uses: Selective allylic substitution, good source of Br₂

H₂/Pd, Pt, Ni

Adds: H₂

Notes: Hydrogenation, Syn Addition → Alkane

Br₂ & Cl₂

Adds: X₂

Notes: Halogenation, Anti-Addition via halonium ion

Br₂ & H₂O

Adds: Br +OH

Notes: Halohydrin Formation, OH to more substituted carbon

HCl, HBr, HI

Adds: H + X

Notes: Hydrohalogenation, Markovnikov Addition

HBr + ROOR

Adds: H + Br

Notes: Hydrohalogenation, Anti - Markovnikov Addition

H₃O+

Product: Alcohol

Notes: Hydration, Markovnikov Addition, Carbocation Reaarangements

Hg(OAc)₂, H₂O/NaBH₄

Product: Alcohol

Notes: Hydration, Markovnikov Addition, No Carbocation Intermediate

BH₃, THF/ H₂O₂, NaOH, H₂O

Product: Alcohol

Notes: Hydration, Anti-Markovnikov Addition, Syn Addition

KMnO₄

Oxidizes: Strong Oxidant

Notes: Cleaves Alkenes, Oxidizes Alcohols

NaNH₂

Product: Acetylide Ion

Notes: Alkyne Reactions, Strong Base, Forms Nucleophile

H₂/Lindlar’s Catalyst

Product: Cis-Alkene

Notes: Alkyne Reactions, Partial Hydrogenation

Na/NH₃(I)

Product: Trans-Alkene

Notes: Alkyne Reactions, Dissolving Metal Reduction

SOCl₂

Uses: Substitution Reaction, Converts ROH → RCl, Inversion of Stereochemistry

HX

Uses: Substitution Reaction, Converts ROH → RX, SN1 or SN2 Reactions

PBr₃

Uses: Substitution Reaction, Converts ROH → RBr, SN2 Reaction, Inversion of Stereochemistry

SN2 Reactions

Reagents: Strong Nucleophiles, Full Negative Charge, Rapidly Donates Electrons

Notes: Primary Substrates

SN1 Reactions

Reagents: Weak Nucleophiles, Donate Electrons Slowly, Neutral Charge

Notes: Tertiary Substrates, Carbocation Rearrangements

E2 Reactions

Reagents: Strong Bases, Readily Accepts Protons, Localized Negative Charges

Notes: Anti-periplanar Hydrogens

E1 Reactions

Reagents: Weak Bases, Neutral or Resonance-Stabilized Compounds

Notes: Carbocation Rearrangements

THF

Solvent Type: Aprotic

Use: Grignard Reactions, BH₃

Ether (ROR)

Solvent Type: Aprotic

Use: Organometallics

DMSO

Solvent Type: Polar Aprotic

Use: SN2 Reactions

Water

Solvent Type: Protic

Use: SN1 Reactions

Alkene → Alkane

Use: H₂/Pd

Why: Syn Addition, Removes All Pi Bonds

Alkene → Markovnikov Alcohol

Use: H₃O+ (acid-catalyzed hydration)

Why: Stable Carbocation Intermediate

Alkene → Markovnikov Alcohol (no rearrangements)

Use: Hg(OAc)₂,H₂O/NaBH₄

Why: Syn Addition, No Carbocation

Alkene → Anti-Markovnikov Alcohol

Use: BH₃,THF/H₂O₂, NaOH, H₂O

Why: Syn Addition, No Carbocation Rearrangement

Alkene → Markovnikov Alkyl Halide

Use: HBr, HI, HCl

Why: Hydrogen Adds to Carbon with More Hydrogens Already Attached Forming the More Stable Carbocation, Carbocation Rearrangements

Alkene → Anti-Markovnikov Alkyl Bromide

Use: HBr + ROOR (peroxides)

Why: Radical Mechanisms, Only Works with HBr

Alkene → Vicinal Dihalide (organic molecule with 2 halogens)

Use: Br₂ or Cl₂

Why: Anti-Addition, Halonium ion produced then backside attack for inversion

Alkene → Halohydrin (X + OH)

Use: Br₂/H₂O

Why: OH goes to more substituted carbon

Alkyne → Cis-Alkene

Use: H₂/Lindlar’s Catalyst

Alkyne →Trans-Alkene

Use: Na/NH₃(I)

Why: Dissolving Metal Reaction

Alkyne → Alkane

Use: H₂ /Pd (excess)

Alkyne → Carbon-Carbon Bond Formation

Use: 1) NaNH₂ 2) R-X (primary)

Why: Forms Acetylide Nucleophile

Alcohol → Alkene

Use: H₂SO₄ + Heat

Why: Dehydration, Zaitsev Product is Favored (more substituted and more stable), Carbocation Rearrangements are Possible

Primary or Secondary Alcohol → Alkyl Halide

Use: PBr₃

Why: Forms RBr, SN2 Reaction, Inversion of Stereochemistry

Any Alcohol → Alkyl Halide

Use: HX (where X = Cl, Br, or I)

Why: SN1 or SN2 Reactions

Alkyl Halide → Substitution (SN2)

Use: Strong Nucleophile + Primary Substrate

Alkyl Halide → Substitution (SN1)

Use: Weak Nucleophile + Tertiary Substrate, Racemization Occurs

Alkyl Halide → Alkene Through Elimination

Small Base: favors Zaitsev Product (more substituted and more stable)

Bulky Base: favors Hofmann Product (less substituted and less stable)

Alkane → Alkyl Halide

Use: Br₂ / hv, more selective

Strong Base + Beta-Hydrogens

Think E2

Strong Nucleophile + Primary Carbon

Think SN2

Weak Nucleophile + Tertiary Carbon

Think SN1/E1

1) O₃, 2) H₂O₂

Product: oxygen added to pi-bonded carbons that were cleaved, OH added to carbons without substrates

1) O₃, 2) DiSulfide Reagent

Product: oxygen added to pi-bonded carbons that were cleaved, no OH added anywhere

Peroxy Acid (RCO₃H)

Use: Makes Epoxides

Product: Anti-Addition of OH groups

Epoxide + Acid

Nucleophile attacks more substituted carbon, trans product, produces diols (two OH groups)

Epoxide + Base

Nucleophile attacks less substituted carbon, behaves like SN2

Grignard Reagent (RMgX)

Properties: Strong nucleophile & base; adds to carbonyls

Produces: Can open epoxides (forms alcohols) and form new C-C bonds

OrganoLithium Reagents (RLi)

Properties: Stronger nucleophile than Grignard; similar reactions

Produces: Can open epoxides and form new C-C bonds