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Organic Chemistry
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Functional Groups
Hydrocarbons:
Alkane: C-C (R-H)
CH₃-CH₃
CH₃-CH₃
Alkene: C=C (R-CH=CH₂)
CH₂=CH₂
CH₂=CH₂
Alkyne: C≡C (R-C≡C-H)
HC≡CH
HC≡CH
Benzene: Aromatic Ring
C₆H₆
C₆H₆
Oxygen Containing:
Alcohol: -OH
R-OH
R-OH
Ether: -O-
R-O-R'
R-O-R'
Aldehyde: -CHO
R-CHO
R-CHO
Ketone: -CO-
R-CO-R'
R-CO-R'
Carboxylic Acid: -COOH
R-COOH
R-COOH
Nitrogen Containing:
Amine: -NH₂, -NH-, -N-
R-NH₂ (1°), R₂NH (2°), R₃N (3°)
R-NH₂ (1°), R₂NH (2°), R₃N (3°)
Amide: -CONH₂
R-CONH₂
R-CONH₂
Nitrile: -CN
R-CN
R-CN
Nitro: -NO₂
R-NO₂
R-NO₂
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Reaction Mechanisms
Substitution Reactions:
SN1 Mechanism:
• Two-step process
• Carbocation intermediate
• Rate = k[RX]
• 3° > 2° > 1° order
• Carbocation intermediate
• Rate = k[RX]
• 3° > 2° > 1° order
SN2 Mechanism:
• One-step process
• Transition state
• Rate = k[RX][Nu⁻]
• 1° > 2° > 3° order
• Transition state
• Rate = k[RX][Nu⁻]
• 1° > 2° > 3° order
Addition Reactions:
Markovnikov's Rule: H adds to C with more H
Anti-Markovnikov: With peroxides
Syn Addition: Same side (e.g., OsO₄)
Anti Addition: Opposite sides (e.g., Br₂)
Elimination Reactions:
E1 Mechanism:
• Carbocation intermediate
• Zaitsev's rule applies
• Rate = k[RX]
• Competes with SN1
• Zaitsev's rule applies
• Rate = k[RX]
• Competes with SN1
E2 Mechanism:
• Concerted mechanism
• Anti-periplanar geometry
• Rate = k[RX][Base]
• Competes with SN2
• Anti-periplanar geometry
• Rate = k[RX][Base]
• Competes with SN2
Rearrangements:
1,2-Hydride Shift: H⁻ migration
1,2-Alkyl Shift: R⁻ migration
Ring Expansion/Contraction: Stability
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Stereochemistry
Chirality & Optical Activity:
Chiral Center: Carbon with 4 different groups
Enantiomers: Non-superimposable mirror images
Diastereomers: Non-mirror image stereoisomers
Meso Compounds: Internally compensated
Racemic Mixture: 50:50 enantiomer mix
R/S Configuration:
Priority Rules:
1. Atomic number
2. Atomic mass
3. Multiple bonds (C=O > C-O)
1. Atomic number
2. Atomic mass
3. Multiple bonds (C=O > C-O)
Assignment:
Clockwise = R
Counterclockwise = S
Clockwise = R
Counterclockwise = S
Conformational Analysis:
Ethane:
Staggered < Eclipsed
Energy difference: 12 kJ/mol
Staggered < Eclipsed
Energy difference: 12 kJ/mol
Butane:
Anti < Gauche < Eclipsed
Gauche interaction: 3.8 kJ/mol
Anti < Gauche < Eclipsed
Gauche interaction: 3.8 kJ/mol
Cyclohexane:
Chair < Boat < Twist boat
Axial vs Equatorial positions
Chair < Boat < Twist boat
Axial vs Equatorial positions
Geometric Isomerism:
E/Z Nomenclature:
E (entgegen) = opposite
Z (zusammen) = together
E (entgegen) = opposite
Z (zusammen) = together
Cis/Trans:
For disubstituted alkenes
Cis = same side, Trans = opposite
For disubstituted alkenes
Cis = same side, Trans = opposite
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Important Named Reactions
Carbon-Carbon Bond Formation:
Aldol Condensation:
R-CHO + R'-CH₂-CHO → β-hydroxy aldehyde
R-CHO + R'-CH₂-CHO → β-hydroxy aldehyde
Grignard Reaction:
RMgX + C=O → tertiary alcohol
RMgX + C=O → tertiary alcohol
Friedel-Crafts:
ArH + RCOCl/AlCl₃ → ArCOR
ArH + RCOCl/AlCl₃ → ArCOR
Diels-Alder:
Diene + Dienophile → Cyclohexene
Diene + Dienophile → Cyclohexene
Oxidation-Reduction:
Jones Oxidation:
1° alcohol → carboxylic acid (CrO₃)
1° alcohol → carboxylic acid (CrO₃)
PCC Oxidation:
1° alcohol → aldehyde
1° alcohol → aldehyde
Swern Oxidation:
Alcohol → carbonyl (DMSO)
Alcohol → carbonyl (DMSO)
Reduction:
LiAlH₄, NaBH₄, Zn/HCl
LiAlH₄, NaBH₄, Zn/HCl
Aromatic Substitution:
Nitration:
ArH + HNO₃/H₂SO₄ → ArNO₂
ArH + HNO₃/H₂SO₄ → ArNO₂
Halogenation:
ArH + X₂/FeX₃ → ArX
ArH + X₂/FeX₃ → ArX
Sulfonation:
ArH + SO₃/H₂SO₄ → ArSO₃H
ArH + SO₃/H₂SO₄ → ArSO₃H
Directing Effects:
Ortho/Para: -OH, -NH₂, -R
Meta: -NO₂, -COOH, -CN
Ortho/Para: -OH, -NH₂, -R
Meta: -NO₂, -COOH, -CN
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Spectroscopic Analysis
IR Spectroscopy:
O-H stretch: 3200-3600 cm⁻¹ (broad)
N-H stretch: 3300-3500 cm⁻¹ (sharp)
C-H stretch: 2800-3100 cm⁻¹
C=O stretch: 1650-1750 cm⁻¹ (strong)
C=C stretch: 1600-1700 cm⁻¹
C-O stretch: 1000-1300 cm⁻¹
¹H NMR Chemical Shifts:
Alkyl CH₃: 0.9 ppm
Alkyl CH₂: 1.3 ppm
CH₂ adjacent to C=O: 2.4 ppm
Aromatic H: 7.0-8.0 ppm
Aldehyde H: 9.5-10.0 ppm
Carboxylic acid H: 10-12 ppm
¹³C NMR Chemical Shifts:
Alkyl carbons: 10-50 ppm
C-O carbons: 50-80 ppm
Alkene carbons: 100-150 ppm
Aromatic carbons: 120-140 ppm
Carbonyl carbons: 160-220 ppm
Mass Spectrometry:
Molecular Ion Peak [M]⁺: Highest m/z
Base Peak: Most intense peak (100%)
Fragmentation: McLafferty rearrangement
Common Losses: -15 (CH₃), -29 (CHO), -45 (COOH)
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Synthesis Strategies
Retrosynthetic Analysis:
1. Identify Target Molecule
Functional groups, stereochemistry
Functional groups, stereochemistry
2. Work Backwards
Transform → Retron → Starting material
Transform → Retron → Starting material
3. Strategic Bond Disconnections
C-C, C-O, C-N bond formations
C-C, C-O, C-N bond formations
4. Evaluate Routes
Yield, selectivity, cost
Yield, selectivity, cost
Protecting Groups:
Alcohol Protection:
TBS (t-BuMe₂Si-), Ac (acetyl)
TBS (t-BuMe₂Si-), Ac (acetyl)
Amine Protection:
Boc (t-BuOCO-), Cbz (PhCH₂OCO-)
Boc (t-BuOCO-), Cbz (PhCH₂OCO-)
Carbonyl Protection:
Acetal/Ketal formation
Acetal/Ketal formation
Carboxyl Protection:
Ester formation (Me, Et, t-Bu)
Ester formation (Me, Et, t-Bu)
Quick Reference Guide
Functional Groups
-OH (alcohol)
-CHO (aldehyde)
-COOH (acid)
Mechanisms
SN1: 3° > 2° > 1°
SN2: 1° > 2° > 3°
E1: Carbocation
Stereochemistry
R/S configuration
E/Z isomerism
Chair conformers
Spectroscopy
IR: C=O 1700 cm⁻¹
¹H NMR: ArH 7-8 ppm
MS: [M]⁺ peak
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