While learning organic chemistry relies on constructive thinking rather than memorizing, there are just too many reactions and reagents you need to remember.
For example, we know that LiAlH4 is a reducing agent that converts aldehydes to primary alcohols, but what about ketones, esters, and amides – Does it work for all of them? Do they follow the same mechanism? How does it compare to DIBAL and NaBH4?
This reagent guide is written to minimize the struggle of searching for reagents. Most of those used in Organic 1 and 2 are summarized in an easy-to-navigate order.
Table of Contents
Ag2O Silver Oxide ……………………………………………… 4
AlBr3 Aluminum Bromide ……………………………………. 4
AlCl3 Aluminum Chloride ……………………………………. 4
Br2 Bromine ……………………………………………………… 6
Cl2 Chlorine ……………………………………………………… 8
CN Cyanide Ion and Nitrile Group ………………………… 9
CrO3 Chromium trioxide …………………………………….12
CuBr Copper (I) Bromide …………………………………….13
CuCl Copper (I) Chloride …………………………………….13
CuI Copper (I) Iodide………………………………………….13
DCC N,N’-dicyclohexane carbodiimide ………………….13
DMS Dimethyl sulfide ………………………………………..14
CH2N2 Diazomethane …………………………………………14
D Deuterium ……………………………………………………15
DIBAL Di-isobutyl aluminum Hydride ……………………15
DMP Dess-Martin Periodinane ……………………………16
DMSO Dimethyl sulfoxide ………………………………….16
EDC ………………………………………………….17
Fe Iron …………………………………………………………….18
FeBr3 Iron (III) Bromide ………………………………………18
FeCl3 Iron (III) Chloride ………………………………………18
RMgX Grignard Reagents ……………………………………19
H2 Hydrogen …………………………………………………….21
H+ and H3O+ ………………………………………………………21
HBr Hydrobromic acid ……………………………………….22
HCl Hydrochloric acid ………………………………………..24
HI Hydroiodic acid …………………………………………….24
H2CrO4 Chromic acid ………………………………………….24
Hg(OAc)2 Mercuric Acetate …………………………………25
HgSO4 Mercuric Sulfate ……………………………………..25
HIO4 Periodic acid ……………………………………………..26
HONO Nitrous Acid ……………………………………………26
HNO3 Nitric Acid ……………………………………………….27
H2O2 Hydrogen peroxide …………………………………… 27
H3PO4 Phosphoric acid ……………………………………… 28
H2SO4 Sulfuric acid …………………………………………… 29
I2 Iodine …………………………………………………………. 29
KMnO4 Potassium permanganate ………………………. 30
tBuOK Potassium tert-butoxide …………………………. 32
LDA Lithium Diisopropyl Amide …………………………. 32
Li Lithium ………………………………………………………. 32
Lindlar’s Catalyst ……………………………………………… 33
LiAlH4 Lithium Aluminum Hydride ………………………. 34
LiAlH(Ot-Bu)3 Lithium tri t-butoxy aluminum hydride 36
MCPBA m-chloroperoxybenzoic acid ………………….. 36
Mg Magnesium ………………………………………………. 37
MsCl Methanesulfonyl chloride …………………………. 37
NaN3 Sodium azide ………………………………………….. 37
Na Sodium ……………………………………………….38
NaBH4 Sodium borohydride ………………………………. 39
NaCNBH3 Sodium cyanoborohydride ………………….. 40
NaBH(OAc)3 Sodium triacetoxy borohydride ………… 40
NaH Sodium hydride ……………………………………….. 40
NaIO4 Sodium periodate …………………………………… 41
NaNH2 Sodium amide ………………………………………. 41
NaOH Sodium hydroxide ………………………………….. 42
NaOEt Sodium Ethoxide …………………………………… 42
NBS N–Bromosuccinimide ………………………………… 42
NCS N–Chloro Succinimide ……………………………….. 43
NIS N–Iodo Succinimide ……………………………………. 44
NH2OH Hydroxylamine …………………………………….. 44
NH3 Ammonia ………………………………………………… 45
NH2NH2 Hydrazine …………………………………………… 45
Ni2B Nickel boride …………………………………………… 46
O3 Ozone ……………………………………………………….. 46
R2CuLi (Gilman) Organocuprates …………………………. 47
RLi Organolithium reagents ………………………………. 48
OsO4 Osmium tetroxide ……………………………………. 50
Pb(OAc)4 Lead tetraacetate ………………………………..50
PBr3 Phosphorus tribromide ……………………………….51
PCl3 Phosphorus trichloride …………………………………51
PCl5 Phosphorus Pentachloride ……………………………52
P2O5 Palladium on carbon ………………………………….52
Pt Platinum ……………………………………………………..53
PCC Pyridinium chlorochromate ………………………….53
POCl3 Phosphorus oxychloride …………………………….54
Ph3P Triphenylphosphine …………………………………..54
PPI Potassium Phthalimide …………………………………55
Py Pyridine ………………………………………………………55
Ra-Ni Raney Nickel ……………………………………………56
RO-OR Peroxides ………………………………………………56
SO3 Sulfur trioxide …………………………………………….57
SOBr2 Thionyl bromide ………………………………………57
SOCl2 Thionyl chloride ……………………………………….58
Sn Tin ……………………………………………………………..58
TBAF Tetrabutyl ammonium Fluoride …………………..58
TMSCl Trimethylsilyl chloride ……………………………..59
TsCl p-Toluenesulfonyl chloride …………………………..59
TsOH p-Toluenesulfonic acid ………………………………59
Zinc …………………………………………………………………60
Oxidizing Agents ……………………………………………….61
Reducing Agents ……………………………………………….61
Most Common Protic and Aprotic Solvents…….61
You may also consider getting the Organic Chemistry 1 and 2 Study Guides where the reactions are summarized from the perspective of the functional groups. For exampe, the study guide for the reactions of alkenes, alkynes, alcohols, etc. will have the most common reactions of these compounds in one place. 
Detailed Beautiful Powerful
Content
Organic I and II
- Lewis Structures, Resonance Structures, and Formal Charges
- Geometry and Hybridization
-
Functional Groups
-
Molecular Representations
- Bond Characteristics-Types, Length, Strength, and Dipole Moment
- Intermolecular Interactions and Physical Properties
- Acids and Bases
- An Introduction to Nomenclature and IUPAC Rules
- Conformations of Alkanes and Cycloalkanes
- Stereochemistry and Chirality
- Nucleophilic Substitution – SN1 an SN2
- Elimination Reactions – E1 and E2
- Competition in Substitution and Elimination Reactions; SN1/E1 vs SN2/E2
- Reactions of Alkenes
- Reactions of Alkynes
- Reactions of Alcohols
- Reactions of Amines and Epoxides
- The Diels-Alder Reaction
- Reactions of Aromatic Compounds
- Reactions of Aldehydes and ketones
- Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
- Alpha Carbon Chemistry: Enols and Enolates
- Carbohydrates
- IR Spectroscopy
- NMR Spectroscopy
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