Organic Chemistry Reactions and the Equations (Tabulated) By Carol Dandira -This is also part of my Conceptualised notes document Reactio n Name What it produces Reacting species Example Equation Conditions, Reagents and Catalysts Notes Crackin g Alkanes Alkenes Longer chain Alkanes

C 12 H 26 ->

C 8 H 18 + C 4 H 8

Al 2 O 3 Heat Complet e Combus tion Alkanes C 4 H 10 + 13 / 2 O 2 -> 4CO 2 + 5H 2 O Incompl ete Combus tion Alkanes C 4 H 10 + 9 / 2 O 2 -> 4CO + 5H 2 O (no soot produced) C 4 H 10 + 3O 2 -> 3C + CO + 5H 2 O(soot produced) Free Radical substitut ion Halogenoalka nes Alkanes C^2 H^6 + Cl^2 -> C 2 H 5 Cl + HCl Cl 2 or Br 2 Ultraviolet light Eliminati on Alkenes Halogeno alkane CH 3 CHBrCH 3 + NaOH→ CH 2 =CHCH 3 + H 2 O + NaBr Ethanolic NaOH Heat Conden sation Amide + HCl Acyl Chloride + Ammonia CH 3 COCl+N H 3 →CH 3 CON H 2 +HCl Room Temperatu re Amide + HCl Acyl Chloride + Primary or Secondar y amine With primary amine CH 3 COCl+C H 3 NH 2 →CH 3 CONHCH 3 +H Cl With secondary amine Room Temperatu re

CH 3 COCl+(C H 3 ) 2 NH→CH 3 CON(CH 3 ) 2 + HCl Dehydra tion Alkenes, Water Alcohol CH 3 CH 2 OH -> CH 2 CH 2 + H 2 O Heated Catalyst e.g. Al 2 O 3 Or concentrat ed acid e.g. conc. H 2 SO 4 Oxidatio n Diol Alkene Cold, dilute, KMnO 4 Carbon dioxide hot concentrat ed acidified KMnO 4 2 hydrogens on the double bond Carbon Carboxylic acid Carbon atom in double bond has 1 hydrogen Ketone Carbon atom in double bond has no hydrogen Carbonyl compounds Alcohol CH 3 CH 2 OH+[ O]-> CH 3 CHO+H 2 O Acidified K 2 Cr 2 O 7 Or acidified KMnO 4 Distillation Primary alcohols give aldehydes which can be further oxidised to carboxylic acids. Secondary alcohols give ketones Tertiary alcohols cannot be oxidised Carboxylic acids

CH 3 COOH+2

[O]->

2CO 2 +2H 2 O

Acidified K 2 Cr 2 O 7 Or acidified KMnO 4 Reflux

Carbon dioxide and water Methanoi c acid

HCOOH+[O]

->CO 2 +H 2 O

Fehling’s reagent or Tollens’ reagent or acidified KMnO₄ or acidified K₂Cr₂O₇ Benzoic acid Alkylbenz ene + KMnO 4 And then methylbe nzene KMnO 4 Is hot and alkaline Dilute acid is then added to give the benzoic acid Electrop hilic addition Alkane Alkene + hydrogen

C 2 H 4 + H 2 ->

C 2 H 6

Pt/Ni Catalyst Heat Hydrogenation Cyclohexane ring Benzene ring + H 2 Pt/Ni Catalyst Heat Alcohol Alkene + Steam

CH 2 =CH 2 +

H 2 O →

CH 3 CH 2 OH

H 3 PO 4

catalyst Halogenoalka ne Alkene + Hydrogen halide

CH 2 =CH 2 +

HBr → CH 3 CH 2 Br Room temperatur e Halogenoalka ne Alkene + halogen CH 2 CH 2 + Br 2 → CH 2 BrCH 2 Br Addition polymeri sation Alkenes Nucleop hilic substitut ion Alcohol Halogeno alkane CH 3 CH 2 Br + NaOH → CH 3 CH 2 OH + NaBr NaOH Heat Nitrile CH 3 CH 2 Br + CN-^ → KCN in ethanol If it is a primary halogen

CH 3 CH 2 CN +

Br Heat Amine (Primary) CH 3 CH 2 Br + NH 3 → CH 3 CH 2 NH 2 + HBr NH 3 in ethanol Heated under pressure (Identifying) halogen present Ag++Br -^ -> AgBr Aqueous silver nitrate in ethanol  AgCl → White  AgBr → Cream  AgI → Yellow Halogenoalka ne Alcohol + HX ( X is the halogen)

CH 3 CH 2 OH +

HCl → CH 3 CH 2 Cl + H 2 O Alcohol + KCl + conc. H 2 SO 4 / H 3 PO 4 C 2 H 5 OH+KCl +H 2 SO 4 →C 2 H 5 Cl+H 2 O+K HSO 4 Alcohol + PCl 3

3C 2 H 5 OH +

PCl 3 → 3C 2 H 5 Cl + H 3 PO 3 Heat Alcohol + PCl 5 C 2 H 5 OH+PCl 5 →C 2 H 5 Cl+PO Cl 3 +HCl Alcohol + SOCl 2

C 2 H 5 OH+SO

Cl 2 →C 2 H 5 Cl+ SO 2 +HCl Diazonium salt -> Phenol Phenyla mine + HNO 2 (Or NaNO 2 ) + Dilute acid

C 6 H 5 NH 2 +HN

O 2 +HCl→C 6 H 5 N 2 +Cl−+2H 2 O To phenol C 6 H 5 N 2 +Cl− +H 2 O→C 6 H 5 O H +N 2 +HCl Dilute acid < 10 degrees Celsius Diazonium salt then further warming with H 2 O to give phenol Acyl Chlorides Carboxyli c acids + PCl 3

3CH 3 COOH+

PCl 3 →3CH 3 C OCl+H 3 PO 3

Carboxyli c acids + PCl 5 Heat Carboxyli c acids + SOCl 2

CH 3 COOH+S

OCl 2 →CH 3 C OCl+SO 2 +HC l Secondary Amine Halogeno alkane + Primary amine CH 3 CH 2 Br+CH 3 NH 2 →CH 3 CH 2 NHCH 3 +HBr Primary amine is in ethanol Heat under pressure Reducti on Amine (Primary) Amide CH 3 CONH 2 + 4[H]-> CH 3 CH 2 NH 2 + H 2 O Reducing agent: LiAlH₄ CO group is reduced Nitrile CH 3 CH 2 CN+4 [H]->CH 3 CH 2 CH 2 NH 2 LiAlH₄ or H 2 /Ni Phenylamine Nitrobenz ene, Sn/HCl, followed by NaOH Sn is hot HCl is concentrat ed NaOH is aqueous Na Alcohol Aldehyde or ketone Aldehyde CH 3 CHO+2[H] ->CH 3 CH 2 OH Ketone CH 3 COCH 3 +2[ H]→CH 3 CH(O H)CH 3 NaBH 4 Or LiAlH 4 Carboxyli c acid

CH 3 COOH+4

[H]->CH 3 CH 2

OH+H 2 O

LiAlH 4 Primary alcohol is formed Hydroly sis Ester Acidic Hydrolysis: C H 3 COOCH 2 C H 3 +H 2 O→CH 3 COOH+CH 3 CH 2 OH Alkaline Hydrolysis Dilute acid or dilute alkali Heat Followed by acidificatio n

(Saponificati on): CH 3 COO CH 2 CH 3 +Na OH→CH 3 CO O−Na++CH 3 C H 2 OH Nitrile Acidic :CH 3 CH 2 CN+2H 2 O+H Cl→CH 3 CH 2 C OOH+NH 4 Cl Alkaline :CH 3 CH 2 CN+NaOH +H2O→CH 3 C H 2 COO−Na++N H 3 Acidification : + H+^ -> CH 3 COOH + Na+ Dilute acid or dilute alkali Followed by acidificatio n Carboxylic Acid + HCl Acyl Chloride + H 2 O CH 3 COCl+H 2 O→CH 3 COO H+HCl Room Temperatu re Amide + Aqueous alkali or aqueous acid With (aq) alkali CH 3 CONH 2 + NaOH→CH 3 COO−Na++N H 3 With acid: Combus tion Alcohol + Oxygen

C 2 H 5 OH+3O 2

→2CO 2 +3H 2

O

Redox Alcohol + Na

2CH 3 CH 2 OH

+2Na→2CH 3 CH 2 O−Na++H 2 Sodium phenoxide and H 2 Phenol + Na C 6 H 5 OH+Na →C 6 H 5 O−Na+ +^1 / 2 H 2

Carbon dioxide Ethanedi oic acid, KMnO₄ 5H 2 C 2 O 4 +2Mn O 4 −+6H+→10C O 2 +2Mn2++8H 2 O KMnO₄ is warm and acidified Esterific ation Ester Carboxyli c acid + alcohol

H 2 SO 4

Also Ester + HCl Acyl condensation Chloride + Alcohol Room Temperatu re Acyl Chloride + Phenol Electrop hilic substitut ion Halogenoare nes (Aryl halides) Arene + Cl 2 Or Br 2 AlCl 3 or AlBr 3 catalyst Nitration Nitrobenzene Benzene + HNO 3 + H 2 SO 4 Temperatu re between 25 and 60 degrees Celsius Electrophilic Substitution 2-nitrophenol and 4-nitrophenol Phenol + HNO 3 HNO 3 is dilute Room temperatur e Bromina tion 2,4,6-tribrom ophenol Phenol + Br 2

2-4-6

tribromophen ylamine Phenyla mine + Br 2 Room Temperatu re The NH 2 group activated the benzene ring more reactive. Because the lone lone pair of electrons on the nitrogen is delocalised into the benzene ring increasing electron density in the ring. The NH 2 group directs incoming groups to the positions 2, 4 and 6orthoparadirecti ng FriedelCrafts Alkylatio n 4-Methyl-Chl orobenzene( major) Arene + CH 3 Cl AlCl 3 Heat FriedelCrafts Acylatio n Aryl Ketone + HCl Arene + CH 3 COCl AlCl 3 Heat Neutrali sation E.g with NaOH produces Sodium Phenoxide Phenol + base Coupling reaction Azo compounds Phenol + NaOH and then Diazonium salts Phenol is dissolved in aqueous sodium hydroxide After the initial reaction, the product reacts with Diazonium salts to produce azo compounds

Diazonium is a strong electrophile. It readily reacts with phenol and phenol substituted compounds to form highly coloured compounds called azo compounds. To increase the solubility, ionic groups are usually added to the phenol. Uses of azo compounds: highly coloured so used in the fabric industry as dyes. Conden sation polymeri sation Polyester Diol + dicarboxy lic acid/ Dioyl chloride Hydroxyc arboxylic acid

Polyamide Diamine + dicarboxy lic acid/ dioyl chloride Aminocar boxylic acid Amino acids Each amino acid has 2 functional groupsCarboxylic acid(C-terminal) which is always on the right, Amine (Nterminal end) Amino acids show properties of both acids and bases: amphoteric. The COOH group make amino acids, behave like acids. The N terminal end gives amino acids their basic properties because the nitrogen has a lone pair of electrons which take up protons in solution. Amino acids in solution: in solutions, amino acids exist as dipolar or neutral ions with a positive N terminal end and a negative C terminal end.. Nucleop hilic addition Hydroxynitrile s Aldehyde s/ Ketones + HCN

CH 3 COH +

HCN ->

CH 3 CH(OH)C

N (update)

KCN

catalyst Heat _Reaction produces a mixture of two isomeric products of equal concentrations called a racemic mixture. This is because the nucleophile can attack the carbonyl carbon from above or below the plane because the carbonyl molecule is tribunal planar._ COOH group is meta directing

CH 3 group is orthopara directing Reactions of amino acids:

In solution, amino acids exist as Zwitter ions. Zwitter ion is formed when the Carboxylic acid end of the amino

acid donates a proton to the N terminal. The pH at which the Zwitter ion exists is called the isoelectric point. Zwitter ions are acidic because of the positively charged N terminal end. Zwitter ions are basic because of the oxygen which has a lone pair of electrons. The isoelectric point of amino acid Q below is 6.2. Draw the Zwitter ion at its isoelectric point.

2. The amino acid is placed in a solution of pH 4.6. Draw the structure of the amino acid at this pH. : when the amino acid is placed in pH below its isoelectric point, it is in an acidic environment. The C-terminal is protonated, the amino acid exists as a cation. At pH above the isoelectric point, the N terminal end donates protons into solution. The amino acid will exist as an anion.