Organic Chemistry Reactions

• The study notes describe various organic chemistry reactions and transformations

Alkane Reactions

• Alkanes can be transformed into alkenes through free radical substitution, using Cl₂ and UV light

Alkene Reactions

• Alkenes can be produced from haloalkanes via elimination with KOH(alc) under reflux
• Alkenes are formed from alcohols through dehydration/elimination with concentrated H₂SO₄(aq)
• Alkenes undergo hydrogenation with H₂ and a Ni/Pt catalyst at 150°C to form alkanes
• Alkenes turn bromine water (Br₂(aq)) from orange to colorless via electrophilic addition
• Alkenes undergo electrophilic addition with HX or X₂

Haloalkane Reactions

• Haloalkanes can react with AgNO₃ to release X⁻, forming a precipitate via nucleophilic substitution
• Haloalkanes form alcohols through nucleophilic substitution with KOH(aq)
• Haloalkanes can also form 1° amines through nucleophilic substitution with excess NH₃(alc)

Alcohol Reactions

• Alcohols can be produced from alkenes through electrophilic addition with dil. H₃PO₄(aq)
• Alcohols are produced from ketones and aldehydes via reduction with NaBH₄
• Alcohols can be transformed into haloalkanes, using reagents like HCl (ZnCl₂ cat), HBr, or PI₃
• 1° and 2° alcohols can be oxidized using H⁺/Cr₂O₇²⁻, with 1° alcohols forming aldehydes (distillation) or carboxylic acids (reflux) and 2° alcohols forming ketones (reflux)
• 3° alcohols cannot be oxidized using these conditions (NVR = No Visible Reaction)
• Alcohols can react with carboxylic acids (or R-COCl) with a concentrated H₂SO₄ catalyst to produce esters via esterification

Nitrile Reactions

• Nitriles are formed from haloalkanes via nucleophilic substitution with KCN(aq+alc) under reflux
• Nitriles can be reduced to 1° amines using LiAlH₄ (ether) under reflux
• Nitriles are hydrolysed with H⁺/H₂O to produce carboxylic acids
• Nitriles can be dehydrated using P₄O₁₀ to form carboxylic acids

Carbonyl Compound Reactions

• Aldehydes and ketones can be identified using the carbonyl test with 2,4-DNPH, which gives a yellow/orange precipitate

Aldehyde Reactions

• Aldehydes can be produced from 1° alcohols via oxidation with H⁺/Cr₂O₇²⁻ followed by distillation
• Aldehydes are oxidized with H⁺/Cr₂O₇²⁻ under reflux to form carboxylic acids
• Aldehydes form a silver mirror with Tollen's reagent and a red precipitate with Fehling's solution

Ketone Reactions

• Ketones are produced from 2° alcohols via oxidation with H⁺/Cr₂O₇²⁻ under reflux

Carboxylic Acid Reactions

• Carboxylic acids are produced from alcohols by oxidation (reflux), nitriles by hydrolysis with H⁺/H₂O
• Carboxylic acids react with Na₂CO₃(aq) or (s) to produce effervescence
• Carboxylic acids can be converted to acyl chlorides using PCl₅ (ether)

Ester Reactions

• Esters are formed from alcohols and refluxing carboxylic acids with concentrated H₂SO₄ catalyst (or + R-COCl) via esterification, they are sweet smelling
• Esters are hydrolyzed back to alcohols and carboxylic acids in the presence of H⁺/H₂O

Acyl Chloride Reactions

• Acyl chlorides react with water to produce misty fumes of HCl
• Acyl chlorides react with NH₃(RT) to produce 1° amides

1° Amide Reactions

• 1° Amides are formed from carboxylic acids with concentrated NH₃(RT) or acyl chlorides with NH₃(RT) via nucleophilic addition-elimination
• 1° Amides are hydrolyzed with H₂O/H⁺ or H₂O (RT) either with acid or water

1° Amine Reactions

• 1° Amines are formed from haloalkanes via nucleophilic substitution with XS NH₃(alc)
• 1° Amines are formed from nitriles via reduction with LiAlH₄ (ether) under reflux

Benzene Reactions

• Benzene reacts with concentrated HNO₃ and concentrated H₂SO₄ to form nitrobenzene via electrophilic substitution
• Benzene reacts with Br₂ and a FeBr₃ catalyst, it forms bromobenzene via electrophilic substitution
• Benzene reacts with Cl₂ and a AlCl₃ catalyst, it forms chlorobenzene via electrophilic substitution
• Benzene reacts with R-Cl and a AlCl₃ catalyst, it forms alkylbenzene via electrophilic substitution (Friedel-Crafts' Alkylation)

Nitrobenzene Reactions

• Nitrobenzene reacts with Sn / c.HCl followed by NaOH(aq), reduction forms phenylamine

Phenylamine Reactions

• The amine group can still undergo nucleophilic substitution & nucleophilic addition-elimination from here!
• Phenylamine reacts with HCl and NaNO₂ at <10°C it forms Benzene-diazonium chloride

Phenol Reactions

• Phenol reacts in room temperature with Br₂, it forms 2,4,6-tribromophenol
• Phenol reacts with dil. HNO₃(aq), it forms 2-nitrophenol
• Phenol reacts with FeCl₃(aq), a yellow to purple colouration occurs

Other Notations

• NB. Carbonyl groups can still undergo reduction & nucleophilic addition from here!
• NB. R group can still undergo free-radical substitution from here!