OChem Reagents

H-X (HCl, HBr)

Addition of Halogen Halide (Markovnikov; Mix of SYN & ANTI)

HBr & H₂O₂

Free Radical HBr Addition (Anti- Markovnikov; Mix of SYN & ANTI)

X₂ (Cl₂, Br₂)

Halogen Addition (Anti/Trans Addition)

X₂ (Cl₂, Br₂) & H₂O

Halohydrin Formation (Anti/Trans Addition)

H₃O⁺ & H₂O

Acid-Catalyzed Hydration (Markovnikov w/ Rearrangement)

1) Hg(OAc) & H₂0

2) NaBH₄

Oxymercuration / Demercuration (Markovnikov w/ NO rearrangement, Anti Addition)

1) Hg(OAc) & ROH (CH₃OH)

2) NaBH₄

Alkoxymercuration / Demercuration (Markovnikov w/ NO rearrangement, Anti Addition)

1) BH₃ & THF

2) H₂O₂ & ^-OH

Hydroboration / Oxidation (Anti- Markovnikov; SYN Addition)

mCPBA or RCOOOH (Ch₃COOOH; Paracetic Acid)

Epoxidation Ring Formation (Syn Addition)

H₃O⁺ & H₂O

Anti Dihydroxylation by Epoxide Opening (ANTI Addition; Formation of a Diol)

1) OsO₄ or KMnO₄ (cold, dilute)

2) H₂O₂ or ^-OH & H₂O

SYN Dihydroxylation (Formation of a Diol)

1) O₃

2) DMS or Me₂S

Ozonolysis

1) KMnO₄ (warm, concentrated)

Permanganate Cleavage (Aldehydes are oxidizing to carboxylic acids)

NaNH2

Creates Alkynyl Anion as Nucleophile

H2, Pd/C

Complete Hydrogenation

H2, Lindlar’s Catalyst

CIS Hydrogenation

Sodium & NH3

TRANS Hydrogenation

H2O, H+, Hg2+

Hydration (Markovnikov; Tautomerization Follows)

1) Sia2BH

2) H202, NaOH

Hydroboration (Anti-Markovnikov, Tautomerization Follows)

Helpful in generating aldehydes from terminal alkynes

1) O3 OR KMnO4, -OH, H2O, Heat

2) H2O OR H+

Oxidative Cleavage

ALWAYS Overoxidizes to Carboxylic Acids

Mg⁰ + Et₂O

Organomagnesium reagent (Gringard)

R - Mg - X

Adds to carbonyl compound (aldehydes, ketones) to make alcohol but NO WATER H+

2 eq. Li + hexanes

Organolithium reagent

R - Li ( + LiX)

Adds to carbonyl compounds (aldehyes, ketones) to make alcohol but NO WATER H+

NaBH₄

Reducing agent for aldehydes and ketones, converting them into alcohols

LiAlH₄ (LAH)

Reducing agent for aldehydes, ketones, esters, and carboxylic acids

PBr₃

Converts alcohols to bromides via substitution SN2 with INVERSION OF CONFIGURATION

SOCl₂

Converts alcohols to chlorides via substitution with RETENTION OF CONFIGURATION

TsCl + pyridine

Converts alcohols to tosylates (a strong leaving group)

with RETENTION OF CONFIGURATION

RO^- + R-LG via SN2 makes ROR

Williamson Ether Synthesis

R must be unhindered (methyl or primary) with leaving group as X or OTs

NaOCl / TEMPo

Oxidizing agent that converts alcohols to carbonyl compounds (aldehydes and ketones)

Swern

Oxidizing agent that converts alcohols to carbonyl compounds (aldehydes and ketones)

DMP or PCC

Oxidizing agent that converts alcohols to carbonyl compounds (aldehydes and ketones)

Excess NaOCl with H₂O

Oxidizing agent that converts alcohols to carbonyl compounds (aldehydes and ketones) and will over-oxidize aldehydes into carboxylic acids

Chromic acid with H₂O

Oxidizing agent that converts alcohols to carbonyl compounds (aldehydes and ketones) and will over-oxidize aldehydes into carboxylic acids