ReagentCatalyst
18-Crown-6
Phase transfer catalyst, cation complexation
C₁₂H₂₄O₆
Octet · Organic library
One searchable library for the whole course.
Search and save the full Octet organic chemistry reference library.
- 83 reactions
- 63 reagents
- 25 functional groups
- 109 reference rows
83Reactions
63Reagents
25Groups
109Reference rows
0Saved
0%Quiz accuracy
Study tipspectroscopy
¹H NMR Integration
Integration tells you relative number of hydrogens. A 3:2:2 ratio with peaks at 1, 3.5, 4 ppm suggests CH₃-CH₂-O-CH₂ pattern.
Protecting group
Acetal
Stable to base, nucleophiles, reducing agents. Removed by acid.
ReactionCarbonyl
Acetal Formation
Remove water
pKa
Acetic acid (CH₃COOH)
pKa 4.76
4.76
ReactionSubstitution
Acetoacetic Ester Synthesis
Makes substituted ketones (methyl ketones), Decarboxylation of β-keto acid, Can alkylate twice, Partner: malonic ester synthesis (makes acids)
pKa
Acetone (α-H)
Enolizable
20
pKa
Acetonitrile (α-H)
pKa 25
25
Protecting group
Acetyl
Forms ester (for OH) or amide (for NH₂). Removed by base hydrolysis.
pKa
Acetylene (≡C-H)
Terminal alkyne
25
ReactionCarbonyl
Acid-Catalyzed Ester Hydrolysis
Aqueous acid, reflux
ReactionCarbonyl
Acyl Chloride Formation
SOCl₂ most common - gaseous byproducts escape, Acyl chlorides very reactive - use quickly, React with alcohols → esters, amines → amides
Functional groupHalides
Acyl Halide (Acid Chloride)
Carbonyl with halide. Most reactive carboxylic acid derivative. Reacts violently with water.
R-COX
IR
Acyl halide C=O
Absorbs at 1795-1815 cm⁻¹
1795-1815
Functional groupOxygen
Alcohol
Hydroxyl group attached to sp³ carbon. Versatile, can be oxidized or act as nucleophile.
R-OH
ReactionElimination
Alcohol Dehydration
Concentrated acid, heat
E1Zaitsev product (more substituted alkene)
IR
Alcohol O-H
Absorbs at 3200-3600 cm⁻¹
3200-3600
ReactionSubstitution
Alcohol to Alkyl Bromide (PBr₃)
OH is poor leaving group - PBr₃ activates it, Works for 1° and 2° alcohols, Alternative: SOCl₂ for chlorides
Inversion (SN2 mechanism)
ReactionSubstitution
Alcohol to Alkyl Chloride (SOCl₂)
Byproducts are gases - easy purification, Pyridine added to neutralize HCl, Works well for 1° and 2° alcohols
Functional groupOxygen
Aldehyde
Carbonyl at end of chain. Electrophilic carbon, easily oxidized to carboxylic acid.
R-CHO
H NMR
Aldehyde (R-CHO)
¹H shift 9.5-10.0 ppm
9.5-10.0
IR
Aldehyde C-H
Absorbs at 2700-2850 cm⁻¹
2700-2850
IR
Aldehyde C=O
Absorbs at 1720-1740 cm⁻¹
1720-1740
Study tipspectroscopy
Aldehyde NMR Signature
Aldehyde proton appears 9.5-10 ppm (very deshielded). IR shows two peaks around 2700-2850 cm⁻¹ (Fermi doublet).
ReactionCarbonyl
Aldol Addition
Low temperature for addition (warm for condensation)
ReactionCarbonyl
Aldol Condensation
Condensation = addition + elimination of water, Heat favors elimination (entropy), Product is α,β-unsaturated carbonyl
Functional groupHydrocarbons
Alkane
Saturated hydrocarbons with only C-C single bonds. Least reactive functional group.
CₙH₂ₙ₊₂
pKa
Alkane (C-H)
Essentially non-acidic
~50
IR
Alkane C-H (sp³)
Absorbs at 2850-3000 cm⁻¹
2850-3000
Functional groupHydrocarbons
Alkene
Unsaturated hydrocarbons with C=C double bond. Nucleophilic, undergo addition reactions.
CₙH₂ₙ
pKa
Alkene (=CH)
~44
IR
Alkene =C-H (sp²)
Absorbs at 3000-3100 cm⁻¹
3000-3100
IR
Alkene C=C
Absorbs at 1620-1680 cm⁻¹
1620-1680
Functional groupHalides
Alkyl Halide
Halogen on sp³ carbon. Undergo substitution (SN1/SN2) and elimination (E1/E2).
R-X (X = F, Cl, Br, I)
Functional groupHydrocarbons
Alkyne
Unsaturated hydrocarbons with C≡C triple bond. Terminal alkynes are weakly acidic.
CₙH₂ₙ₋₂
IR
Alkyne ≡C-H (sp)
Absorbs at 3300 cm⁻¹
3300
IR
Alkyne C≡C
Absorbs at 2100-2260 cm⁻¹
2100-2260
H NMR
Allylic (C=C-CH)
¹H shift 1.6-2.0 ppm
1.6-2.0
ReagentCatalyst
Aluminum Chloride
Lewis acid catalyst
AlCl₃
Functional groupNitrogen
Amide
Carbonyl + nitrogen. Very stable, found in proteins (peptide bonds).
R-CONH₂
IR
Amide C=O
Absorbs at 1630-1690 cm⁻¹
1630-1690
ReactionCarbonyl
Amide Formation from Acyl Chloride
Use 2 eq amine (one acts as base) or add Et₃N, Most stable carboxylic acid derivative, Peptide bonds are amide bonds
IR
Amide N-H
Absorbs at 3150-3400 cm⁻¹
3150-3400
H NMR
Amide N-H
¹H shift 5-8 ppm
5-8
IR
Anhydride C=O
Absorbs at 1740-1840 cm⁻¹
1740-1840
ReactionAddition
Anti Dihydroxylation (Epoxide Opening)
Acid-catalyzed: opens at more substituted carbon, Base-catalyzed: opens at less substituted carbon
Anti addition (OHs on opposite faces)
Study tipmechanism
Anti-Markovnikov Addition
HBr + peroxides (ROOR) = anti-Markovnikov via radical mechanism. Only works with HBr (not HCl or HI). Hydroboration-oxidation also gives anti-Markovnikov alcohols.
ReactionAddition
Anti-Markovnikov HBr Addition (Radical)
Peroxide initiator (light or heat)
Anti-Markovnikov: Br on less substituted carbon
ReactionSubstitution
Appel Reaction
ROH → RX conversion, CBr₄ for bromides, CCl₄ for chlorides, CI₄ for iodides, Mild conditions, Alternative to PBr₃, SOCl₂
H NMR
Ar-OH (phenol)
¹H shift 4-8 ppm
4-8
C NMR
Aromatic C (general)
¹³C shift 110-160 ppm
110-160
C NMR
Aromatic C-C (ipso)
¹³C shift 125-150 ppm
125-150
IR
Aromatic C-H
Absorbs at 3000-3100 cm⁻¹
3000-3100
C NMR
Aromatic C-H
¹³C shift 110-130 ppm
110-130
C NMR
Aromatic C-O
¹³C shift 150-165 ppm
150-165
IR
Aromatic C=C
Absorbs at 1450-1600 cm⁻¹
1450-1600
Study tipgeneral
Arrow Pushing
Arrows flow from electron-rich (nucleophile) to electron-poor (electrophile). Show all electron pairs. Formal charges must balance across each step.
Functional groupHalides
Aryl Halide
Halogen on aromatic ring. Less reactive than alkyl halides. Undergo SNAr or metal-catalyzed coupling.
Ar-X
ReagentNucleophile
Arylboronic Acids
Coupling partner for Suzuki reactions
ArB(OH)₂
Study tipstereochemistry
Axial vs Equatorial
Bulky groups prefer equatorial position to avoid 1,3-diaxial interactions. A-value = energy difference between axial and equatorial conformations.
245 records still below