Chemistry - Synthesis, organics

H2, heated, Ni catalyst

Electrophilic addition

KMnO4(aq), H+ catalyst

Electrophilic addition

excess H2O, phosphoric acid catalyst, high pressure, high temperatures

Electrophilic addition

Conc phosphoric acid, high temp

Dehydration reaction

HX or X2, not aqueous

Electrophilic Addition

NaOH(eth), reflux

Acid-base reaction

X2, UV

Free radical substitution

Concentrated ammonia, heated in a sealed container

Nucleophilic substitution

KCN(eth), reflux

Nucleophilic substitution

NaOH(aq), reflux

or H20(l), warm

Nucleophilic substitution

Cl: 1,2 PCl5 or 3 conc HCl

Br: NaBr + conc H2SO4 → HBr

I: PI3

Halogenation

Potassium Dichromate, acid, distil

Oxidation

LiAlH4(dry ether) or Using Grignard reagent

Reduction

Potassium dichromate, acid, reflux

Oxidation

LiAlH4(dry ether)

Reduction

RCOOH, acid catalyst or RCOCl, reflux

Esterification

Acid hydrolysis, H20 with acid catalyst, reflux

Alkali hydrolysis, NaOH, reflux then acid to convert carboxylate salt

PCl5

H2O

HCN/KCN (aq), reflux

Nucleophilic addition

Acid and Alkali hydrolysis

Acid and Alkali hydrolysis

side product of amine

conc NH3 or RNH2

acid/alkali hydrolysis or LiAlH4(dry ether)

side product of carboxylic acid

Acyl chloride

LiAlH4 (dry ether)

Reduction

1. Sn + conc HCl, reflux

2. NaOH(aq)

   Reduction reaction

RCOCl, AlCl3 catalyst(electrophile maker)

electrophilic substitution

conc HNO3, conc H2SO4 catalyst

electrophilic substitution

X2, FeX3 catalyst (called a halogen carrier)

electrophilic substitution

RCl, FeCl3 catalyst (called a halogen carrier)

electrophilic substitution

Br2(aq). N.B. Bromination of benzene requires liquid bromine

electrophilic substitution

Bromine water

Positive test = brown to colourless

Negative test = remains brown

Ammonia and silver nitrate (Tollen’s)

First add mix dilute sodium hydroxide with silver nitrate

Add ammonia to dissolve solid silver(I) oxide, then add to suspected aldehyde

Positive test = Silver mirror

Negative test = colourless solution

or

Benedict’s Reagent

Positive test = blue solution to red brick precipitate

Negative test = remains blue

2,4 - DNPH

Positive test = Orange precipitate

Negative test = orange solution

Then collect and recrystallise precipitate.

Take melting point, compare with table of known values

Acidified potassium dichromate

Positive test = Orange solution to green solution

Negative test = remains orange

Bromine (aq/l)

Positive test = Bromine decolourises, white precipitate forms

Negative test = brown solution

Sodium carbonate (s or aq)

Positive test = effervescence

Negative test = colourless solution

Add Iodine and alkali e.g. sodium hydroxide

Yellow precipitate forms, CHI3

Side products, carboxylate salt, water, iodide

By adding Mg to R-Br

Warm in water bath and reflux

Alkane forms, need to store Grignard reagent in dry ether

Forms R-COOMgBr

Then add dilute acid

R-COOMgBr +H₂O —→ R-COOH + Mg(OH)Br

Add Grignard reagent, R-Mg-Br then dilute acid

Form R-CH2OH, a primary alcohol

Add Grignard reagent, R-Mg-Br then dilute acid

Form R-R’-CHOH, a secondary alcohol