Synthetic routes

nitrile or amide → carboxylic acid?

nitrile or amide → carboxylic acid?

• acid hydrolysis under reflux → H⁺/H₂O

• alkaline hydrolysis followed by acidifying the carboxylate salt→ OH⁻/H₂O

halogenoalkane → nitrile?

• KCN dissolved in ethanol

• warm

nitrile → amine?

• LiAlH₄ in dry ether

• H₂ with a Ni catalyst

amide → nitrile?

• P₄O₁₀ (dehydration)

• heat

amine → primary alcohol?

• cold nitrous acid → HONO at 5°C

  • made in situ using NaNO₂ + HCl

carboxylic acid → primary alcohol?

LiAlH₄ in dry ether

methyl benzene → aromatic carboxylic acid?

• potassium manganate in an alkaline solution of sodium hydroxide under reflux

  • dark brown precipitate formed → aromatic carboxylic acid

carboxylic acid → alkane? Name of reaction?

• sodalime

• decarboxylation

carboxylic acid → ester?

alcohol + concentrated H₂SO₄ catalyst under reflux

carboxylic acid → acid chloride?

• SOCl₂

• PCl₃ or PCl₅ but more difficult to separate from end reaction mixture

acid chloride → ester?

• alcohol

• room temperature

acid chloride → carboxylic acid?

water

acid chloride → amide?

ammonia

carboxylic acid → amide?

• ammonia or (NH₄)₂CO₃ → yield ammonium salt of carboxylic acid

• heat strongly to make the amide

halogenoalkane → amine?

reflux in excess alcoholic ammonia under pressure

ammonium salts → amine?

add alkali

acyl chloride → N-substituted amide?

primary amine

amide → amine?

LiAlH₄ in dry ether

nitrobenzene → phenylamine?

• concentrated HCl followed by NaOH

• Sn catalyst

• reflux

phenylamine → diazonium salt?

• HONO (NaNO₂ + HCl in situ)

• <5°C

diazonium salt → phenol?

• above 10°C

• loses nitrogen gas and OH group joins to phenol

diazonium salt → 4-hydroxyazobenzene (yellow)?

• phenol

• <10°C

diazonium salt reaction with naphthalen-2-ol?

• alkaline conditions

• red azo dye produced

benzene → nitrobenzene?

• concentrated H₂SO₄ catalyst

• concentrated HNO₃

• 50°C

benzene → chlorobenzene?

• chlorine and halogen carrier

• anhydrous AlCl₃ or FeCl₃

• reflux in presence of halogen carrier (e.g. AlCl₃ or FeCl₃)

• 50°C

benzene → bromobenzene?

• room temperature

• bromine

• FeBr₃

benzene → methyl benzene?

• chloroalkane (chloromethane/chloroethane)

• anhydrous AlCl₃ catalyst

halogenoalkane → alcohol?

heat halogenoalkane with aqueous solution of alkali (KOH or NaOH)

alkene → alcohol?

• water

• phosphoric acid on silica

• 300°C

• 60 - 70 atm

aldehyde → primary alcohol?

• NaBH₄ in water

• LiAlH₄ in dry ether → not easy to carry out in practice

ketone → secondary alcohol?

• NaBH₄ in water

• LiAlH₄ in dry ether → not easy to carry out in practice

alcohol → halogenoalkane (more than one way)? What are the products formed?

• heat with hydrogen halide

  • concentrated H₂SO₄ catalyst

  • halogenoalkane and water produced

• heat with HCl gas

  • anhydrous ZnCl₂ catalyst

  • chloroalkane produced

• PCl₅

  • chloroalkane, POCl₃ + HCl formed

• SOCl₂

  • chloroalkane + SO₂ + HCl formed

• PI₃

  • iodoalkane +H₃PO₃ produced

primary alcohol → aldehyde?

heat gently with acidified potassium dichromate and dilute H₂SO₄

aldehyde → carboxylic acid?

reflux aldehyde with excess acidified potassium dichromate

primary alcohol → carboxylic acid?

• reflux with excess acidified potassium dichromate

• add potassium manganate → no aldehyde intermediate

secondary alcohols → ketones?

heat with acidified potassium dichromate

alcohol → alkene?

heat with concentrated H₂SO₄

phenol → 2,4,6-tribromophenol? What is observed during this reaction?

• bromine

• white precipitate

phenol → ester?

• acid chloride

• pyridine base → reacts with HCl but not acid chloride (must not react with acid chloride so NaOH not suitable)

aldehyde/ketone → hydroxynitrile/cyanohydrin?

dilute H₂SO₄ added to aqueous solution of aldehyde/ketone dissolved in HCN

hydroxynitrile/cyanohydrin → carboxylic acid?

reflux with dilute H₂SO₄ (or any dilute acid)

ester → carboxylic acid/primary alcohol?

• acid hydrolysis → H⁺/H₂O

• alkaline hydrolysis → OH⁻/H₂O

alkene → halogenoalkane?

HX

halogenoalkane → alkene?

NaOH in ethanol under reflux

alkene → alkane?

• H₂ (g)

• Nickel/platinum catalyst

primary alcohol → ester?

• carboxylic acid

• concentrated H₂SO₄

alkene → dihalogenoalkane?

X₂