Tabulated Organic Chemistry Reactions and Equations
Table of Contents
- Overview
- Cracking and Combustion
- Oxidation of Alcohols and Carbonyl Compounds
- Dehydration, Addition, and Elimination
- Nucleophilic Substitution and Nitriles
- Alcohols, Esters, and Acids
- Amino Acids, Zwitterions, and Isoelectronic Point
- Diazonium Chemistry and Azo Compounds
- Nucleophilic Additions and Cyanides
- Nitriles, Amines, and Amides
- Polymerization and Condensation
- Illustrative Notes on Amino Acids
- Images
- References
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Overview
This document details a tabulated collection of organic chemistry reactions, listing reaction names, products, reacting species, example equations, conditions, reagents, catalysts, and practical notes. It also includes discussion on amino acids, zwitterions, isoelectric points, and related electrophilic and nucleophilic processes. The material spans cracking, oxidation, halogenation, substitution, esterification, nitrile chemistry, diazonium reactions, and polymerization. The data is presented in a structured format to preserve the relationships between reactants, products, and the conditions under which reactions occur. Images accompanying the notes provide visual representations of many tables and reaction schemes.
Cracking and Combustion
| Reaction Name | What it produces | Reacting species | Example Equation | Conditions, Reagents and Catalysts | Notes |
|---|---|---|---|---|---|
| --- | --- | --- | --- | --- | --- |
| Cracking | Alkanes to alkenes; longer-chain alkanes | Alkanes | C12H26 -> C8H18 + C4H8 | Al2O3; Heat | Complete combustion |
| Combustion (Complete) | CO2 and H2O | Alkanes + O2 | C4H10 + 13/2 O2 -> 4 CO2 + 5 H2O | Heat | Complete combustion with excess O2 |
| Incomplete Combustion (soot-free) | CO2, CO, H2O with reduced soot | Alkanes + O2 | C4H10 + 9/2 O2 -> 4 CO + 5 H2O | Heat | No soot produced; CO is a potential pollutant |
| Incomplete Combustion (soot) | CO, CO2, H2O, soot | Alkanes + O2 | C4H10 + 3 O2 -> 3 C + CO + 5 H2O | Heat | Soot produced; carbon balance varies |
| Free Radical Substitution | Halogenated alkanes | Alkanes + Cl2 (or Br2) | C2H6 + Cl2 -> C2H5Cl + HCl | Ultraviolet light | Radical mechanism predominates |
| Elimination (Acylation context) | Amide formation from acyl chlorides | Acyl chloride + Ammonia | CH3COCl + NH3 -> CH3CONH2 + HCl | Room temperature | Amide formation; subsequent steps possible |
| Acyl Chloride + Primary amine | Secondary amide formation | CH3COCl + CH3NH2 -> CH3CONHCH3 + HCl | Room temperature | Primary amine reagents; yields mixed amide products | |
| Acyl Chloride + Secondary amine | Tertiary amide formation | CH3COCl + (CH3)2NH -> CH3CON(CH3)2 + HCl | Room temperature | Secondary amine yields tertiary amide | |
| Dehydration of Alcohols | Alkenes + H2O | Alcohol | CH3CH2OH -> CH2CH2 + H2O | Heated; Al2O3 or conc. H2SO4 | Acid-catalyzed dehydration; Zaitsev orientation often observed |
Oxidation of Alcohols and Carbonyl Compounds
| System | Substrate | Oxidant | Product | Conditions / Notes |
|---|---|---|---|---|
| --- | --- | --- | --- | --- |
| Primary Alcohols | CH3CH2OH | Acidified K2Cr2O7 or acidified KMnO4 | Aldehydes (further oxidized to carboxylic acids) | Primary alcohols give aldehydes; aldehydes can be further oxidized to carboxylic acids; distillation often used to stop at aldehydes |
| Secondary Alcohols | CH3CH(OH)CH3 | Acidified KMnO4 or PCC-like reagents | Ketones | Secondary alcohols give ketones; tertiary alcohols cannot be oxidized |
| Carboxylic Acids | CH3COOH | KMnO4 under reflux (strong oxidation) | CO2 + H2O | Strong oxidation to CO2/H2O under reflux; often complete mineralization; controlled conditions may avoid deep oxidation |
| Diol Oxidation | Diol | Cold, dilute KMnO4 | Various diol cleavage products; sometimes carbonyl compounds | 2 hydrogens on the double bond; cleavage yields carbonyl fragments |
Dehydration, Addition, and Elimination
| Process | Substrates | Reagents | Product/Outcome | Notes |
|---|---|---|---|---|
| --- | --- | --- | --- | --- |
| Alcohol Dehydration | Alcohols to alkenes | Acidic catalysts (e.g., conc. H2SO4) or alumina | Alkenes with water eliminated | Typical E1/E2 mechanisms depending on substrate |
| Electrophilic Addition to Alkenes | Alkenes + H2 | Pt/Ni catalyst; Heat | Alkanes | Hydrogenation; selective catalysts |
| Hydration of Alkenes | Ethene to Ethanol | H3PO4 catalyst | Ethanol | Steam hydration of ethene |
| Halogenation of Alkenes | Alkenes + HBr | Room temperature | Halogenated alkanes | Markovnikov/anti-addition depending on conditions |
Nucleophilic Substitution and Nitriles
| Reaction | Substrate | Nucleophile | Product | Conditions / Notes |
|---|---|---|---|---|
| --- | --- | --- | --- | --- |
| Nucleophilic Substitution (Acidic) | Alcohol derivatives | CN-, NH3, etc. | Nitriles, amines or alcohols | Heating with KCN in ethanol; base presence influences product distribution |
| Nitrile Formation | Primary halide | CN- | Nitrile | Alkyl halide + cyanide source; often heated |
| Reduction to Amine | Nitrile | LiAlH4 or H2/Ni | Primary amine | Reducing conditions; may require workup to amino groups |
Alcohols, Esters, and Acids
| Reaction | Substrates | Reagents | Product | Notes |
|---|---|---|---|---|
| --- | --- | --- | --- | --- |
| Alcohol to Aldehyde/Ketone | Primary or secondary alcohol | Oxidants (acidified KMnO4, acidified K2Cr2O7) | Aldehyde (primary) or Ketone (secondary) | Primary -> aldehyde; secondary -> ketone; distillation or controlled oxidation to stop at aldehyde is common |
| Esterification | Carboxylic acid + Alcohol | H2SO4 (catalyst) | Ester | Also condensation with alcohol and acid chloride; room temperature sometimes |
| Ester Hydrolysis | Ester | H2O, acid or base | Carboxylic acid + alcohol (alcoholysis) | Acidic hydrolysis yields carboxylic acid; alkaline hydrolysis yields carboxylate salt; followed by acidification |
| Saponification (Alkaline Hydrolysis) | Ester | NaOH | Carboxylate salt | Followed by acidification to carboxylic acid |
Amino Acids, Zwitterions, and Isoelectronic Point
Each amino acid has two functional groups: a carboxylic acid (C-terminal) and an amine group (N-terminal). Amino acids exhibit amphoteric behavior due to the acidic carboxyl group and basic amino group. In solution, amino acids exist as dipolar ions (zwitterions) with a positive N-terminal and a negative C-terminal end. The isoelectric point (pI) is the pH where the molecule carries no net charge.
- The isoelectric point of amino acid Q below is 6.2. Draw the zwitterion at its isoelectric point.
- When placed in solution at pH 4.6, the amino acid is in an acidic environment; the C-terminal is protonated, giving a cationic form.
- At pH above the isoelectric point, the amino group donates protons, and the amino acid exists as an anion.
Additional notes on amino acids in solution:
- Zwitter ions are acidic because of the positively charged N-terminus and basic because of the oxygen with a lone pair of electrons.
- The isoelectric point of amino acid Q is 6.2 (illustrated). Draw the zwitterion at this point.
Reactions related to amino acids include: hydrolysis, amidation, peptide coupling (condensation to form peptide bonds), and side-chain chemistry in various conditions. The diagrams in the original notes illustrate the directional layout of NH2 and COOH groups in relation to pH changes and buffer systems.
Nucleophilic Additions and Cyanides
- Hydroxynitrile formations from aldehydes/ketones using HCN or KCN catalysts, often under heat. The reaction produces a mixture of two isomeric products (racemic mixture) when nucleophilic attack occurs from either face of the carbonyl.
- The CN- addition to carbonyls is stereochemically significant due to the planar carbonyl; nucleophilic attack from above or below yields enantiomeric products. The COOH group is meta-directing in some contexts, while CH3 group is ortho-para directing in electrophilic aromatic substitutions (as contextually noted in the document).
Diazoniu m Chemistry and Azo Compounds
Diazonium salts are highly reactive intermediates in aromatic chemistry. Diazonium salts readily react with phenol and phenol-substituted compounds to form highly colored azo compounds, which are extensively used as dyes in the fabric industry. The substitution pattern and directing effects of diazonium salts enable various azo-coupling reactions. To increase solubility, ionic groups are often added to the phenol.
Condenstation and polymerisation sections illustrate how diazonium chemistry can be leveraged for azo coupling and subsequent polymer formation. Azo compounds are characterized by highly colored products and are used widely as dyes in textiles and plastics.
Nitriles, Amines, and Amides
| Reaction | Substrate | Reagent/Conditions | Product | Notes |
|---|---|---|---|---|
| --- | --- | --- | --- | --- |
| Amino acid formation from nitrile | Nitrile + H2O | LiAlH4 or H2/Ni | Primary amine | Reductive amination; further transformations possible |
| Reduction of amide | Amide | LiAlH4 | Primary amine | Reducing conditions; table notes CO group is reduced |
| Amino acids from nitriles | Nitrile + NaOH | H2O; hydrolysis | Carboxylate salt | Alkaline hydrolysis; followed by acidification to obtain acid |
Diazonium Chemistry and Azo Compounds (Continued)
- If it is a primary halogen, a standard KCN or salt approach can yield nitriles from halogenated substrates.
- Diazotization reacts with phenol to form phenol derivatives via azo coupling; diazonium salts can form azo dyes by coupling with phenols and amines.
Nucleophilic Additions and Cyanides (Expanded)
- Hydroxynitrile additions to aldehydes/ketones produce cyanohydrins; the heated reaction with HCN yields mixture products; the presence of CN- catalyzes addition to electrophilic carbon centers. The directing groups influence subsequent electrophilic substitutions on the aromatic ring (meta directing for COOH and ortho/para directing for CH3).
Polymerization and Condensation
- Condensation polymerisation: Polyesters and polyamides form via diol + dicarboxylic acid, or diamine + dicarboxylic acid/dioyl chloride, producing polymer backbones with ester or amide linkages.
- In diacid-diol systems, hydroxycarboxylic acids can participate to form polyesters; in diamine + diacid or diol chloride systems, polyamides form via amide linkages; amino acids can act as monomers in condensed polymer networks.
Illustrative Notes on Amino Acids
- Reactions of amino acids include hydrolysis, amidation, and peptide coupling. The Saponification-like hydrolysis yields carboxylate salts in basic conditions; acid hydrolysis yields carboxylic acids.
- Amino acids are amphoteric; the carboxyl group behaves as an acid and the amine as a base in solution.
- The amino acid diagrams illustrate zwitterions, isoelectric points, and how pH influences charge states.
- The isoelectric point (pI) is the pH where the net charge is zero; for amino acid Q, pI = 6.2.
Images
- Page 1 image: Table of reactions including Dehydration, Oxidation, and Condensation with notes. Alt: "Table of reactions - page 1"; Caption: "Reaction table showing cracking, oxidation, and dehydration data."
- Page 2 image: Continuation table including Nucleophilic substitution and halogenation schemes. Alt: "Table - page 2"; Caption: "Continuation of table data with reagents and conditions."
- Page 3 image: Further continuation with Diazonium chemistry and electrophilic substitution. Alt: "Table - page 3"; Caption: "Diazonium and azo-coupling reaction details."
- Page 4 image: Final continuation with amino acid reactions and polymerization. Alt: "Table - page 4"; Caption: "Amino acid reactions and nitrogen-containing compounds."
References
- The content in this document is adapted from notes by Carol Dandira and accompanying scanned pages that illustrate reaction schemes and tabulated data. The tables include additional notes and diagrams not fully captured in text form here, and the original images provide the most precise representations of reaction schemes and conditions.
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