Organic Chemistry Reagents and Conditions Flashcards by KIN WEI QI VANESSA Year

What functional groups are involved in E Add?

Alkenes

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What functional groups are involved in E Sub?

Benzenes, methylbenzenes, halogenoarenes, phenols, phenylamines

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What functional groups are involved in Nu Add? What do they form?

Aldehydes and ketones to form alcohols

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What functional groups are involved in Nu Sub?

Halogenoalkanes, halogenoarenes, alcohols, carboxylic acids and its derivatives (ester, amide, acyl chloride)
Note: R&C for CA’s derivatives are not in syllabus

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What functional groups can be oxidised?

Alkenes, arenes, primary/secondary alcohols, aldehydes, carboxylic acid

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What functional groups can be reduced?

Alkenes, carbonyls, carboxylic acids, nitriles, nitrobenzene, amides

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There are 5 sets of condensation reactions. Name them.

Alcohol + carboxylic acid
Alcohol + acyl chloride
Phenol + acyl chloride
All carbonyls + 2,4-DNPH
Acyl chloride + ammonia/amine

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Name the 2 elimination reactions.

Elimination of HX from halogenoalkanes

Elimination of H2O (dehydration) from alcohol

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What functional groups are involved in acid-base reactions?

Alcohols, phenols, carboxylic acids, amines (only one that acts as base)

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What is the function of initiation step of FRS?

To form Cl/Br halogen radicals

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What is the function of propagation step of FRS?

To form products (CH3Cl or more) and regenerate radical

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What is the function of termination step of FRS?

All radicals collide

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Reagents and Conditions for FRS

Cl2(g)/Br2(l), UV light (just to kick-start initiation because propagation step is self-sustaining)

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What functional groups are involved in hydrolysis? (addition of water to break compound into 2)

Nitriles, acyl chloride, esters, amides

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R&C for E Add of water

Industrial: steam, H3PO4 as catalyst, high T and P
Lab: water, conc. H2SO4, cold

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R&C for E Add of Cl2/Br2

Cl2(g)/Br2(l), rt, no UV light

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R&C for E Add of bromine water

Br2(aq), rt

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R&C for E Add of hydrogen halides

HBr(g)/HCl(g)/HI(g), rt

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R&C for E Sub: Chlorination/Bromination of benzenes

Cl2(g)/Br2(l), FeCl3(s)/FeBr3(s) as Lewis acid catalyst, warm

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R&C for E Sub: Chlorination/Bromination of methylbenzenes

Cl2(g)/Br2(l), FeCl3(s)/FeBr3(s) as Lewis acid catalyst, rt, no UV

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R&C for E Sub: Bromination of phenols

Br2(l), low temp. (+ 1 -Br) OR Br2(aq), rt (+ 3 -Br)

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R&C for E Sub: Bromination of phenylamines

Br2(aq), rt (+ 3 -Br)

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R&C for E Sub: Nitration of benzenes

Conc. HNO3, conc. H2SO4 as Bronsted-Lowry acid catalyst, maintained at 55℃

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R&C for E Sub: Nitration of methylbenzenes

Conc. HNO3, conc. H2SO4 as Bronsted-Lowry acid catalyst, maintained at 30℃

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R&C for E Sub: Nitration of phenols

Dilute HNO3, rt (+ 1 -NO2) OR conc HNO3, rt (+ 3 -NO2)

R&C for E Sub: Friedal-Crafts alkylation of benzenes

Chloroalkane, AlCl3 as Lewis acid catalyst, warm

R&C for E Sub: Friedal-Crafts alkylation of methylbenzenes

Chloroalkane, AlCl3 as Lewis acid catalyst, rt

R&C for Nu Sub: halogenoalkanes with OH-

Dilute NaOH, heat

R&C for Nu Sub: halogenoalkanes with CN-

Ethanolic KCN, heat

R&C for Nu Sub: halogenoalkanes with NH3

Ethanolic conc. NH3, heat in sealed tube (prevent NH3 from escaping)

R&C for Nu Sub: primary and secondary alcohols with HCl

Conc. HCl, ZnCl2 as catalyst, heat

R&C for Nu Sub: tertiary alcohols with HCl

Conc. HCl, rt

R&C for Nu Sub: alcohols with HBr

Conc. HBr, heat

R&C for Nu Sub: alcohols with phosphorus trihalides to form halogenoalkanes

PCl3, rt OR P, Br2/I2, heat

R&C for Nu Sub: CA with phosphorus trihalides to form acyl chlorides

PCl3, rt OR P, Br2/I2, heat

R&C for Nu Sub: alcohols with PCl5 to form halogenoalkanes

PCl5, rt

R&C for Nu Sub: CA with PCl5 to form acyl chlorides

PCl5, rt

R&C for Nu Sub: alcohols with thionyl chloride to form halogenoalkanes

SOCl2, warm

R&C for Nu Sub: CA with thionyl chloride to form acyl chlorides

SOCl2, warm

R&C for Oxidation: Mild Oxidation of Alkenes

KMnO4, dilute NaOH, cold

What is added in mild oxidation of alkenes?

Diols (2 OH-)

R&C for Oxidation: Oxidative Cleavage of Alkenes

KMnO4, dilute H2SO4, heat

What is formed in oxidative cleavage of alkenes?

CO2 and H2O, Carboxylic Acids, Ketones (depending on alkene)

R&C for Oxidation: Side-Chain Oxidation of Arenes

KMnO4, dilute H2SO4/NaOH, heat

What is formed in Side-Chain Oxidation of Arenes?

Carboxylic acids

R&C for: Oxidation of Primary Alcohols to form Aldehydes

K2Cr2O7, dilute H2SO4, heat with immediate distillation (to prevent further oxidation into CA)

R&C for: Oxidation of Primary Alcohols to form Carboxylic acids

KMnO4/K2Cr2O7, dilute H2SO4, heat

R&C for: Oxidation of Secondary Alcohols to form Ketones

KMnO4/K2Cr2O7, dilute H2SO4, heat

R&C for: Oxidation of Aldehydes

KMnO4/K2Cr2O7, dilute H2SO4, heat

R&C for: Oxidation of Methanoic Acid and Ethanedioic acid to form CO2 and H2O

KMnO4, dilute H2SO4, heat

R&C for: Reduction of Alkenes

H2(g), Ni catalyst, high P, rt

How many H atoms are added and what is formed in reduction of alkenes?

2, alkane

R&C for: Reduction of Aldehydes and Ketones

LiAlH4 in dry ether, rt OR H2(g), Ni catalyst OR NaBH4 in methanol

How many H atoms are added and what is formed in reduction of aldehydes and ketones?

2, primary and secondary alcohol

R&C for: Reduction of CA

LiAlH4 in dry ether, rt

How many H atoms are added and what is formed in reduction of CA?

4, primary alcohol

R&C for: Reduction of Nitriles

H2(g), Ni catalyst, high P

How many H atoms are added and what is formed in reduction of nitriles?

4, primary amine

R&C for: Reduction of Nitrobenzene

Sn, excess conc. HCl, heat, NaOH(aq)

How many H atoms are added and what is formed in reduction of nitrobenzene?

6, phenylamine

R&C for: Reduction of Amides

LiAlH4 in dry ether

How many H atoms are added and what is formed in reduction of amides?

4, primary amine

R&C for Condensation of Alcohol + CA to form ester

Few drops of conc. H2SO4 as catalyst, heat

R&C for Condensation of Alcohol + Acyl chloride to form ester

R&C for Condensation of Phenol + Acyl Chloride to form phenyl ester

rt (add NaOH or Na for better yield)

R&C for Condensation of Carbonyls + 2,4-DNPH to form orange ppt

R&C for Condensation of acyl chlorides + ammonia/amines to form amides

rt (note: ammonia/amines to be added in excess)

R&C for Elimination of HX from halogenoalkanes

Ethanolic KOH, heat

R&C for Elimination of H2O from alcohol

Excess conc. H3PO4, heat

All acid-base reactions occur at rt. But what are the products/observations of alcohol and sodium metal?

Na ethoxide, slow effervescence of H2(g)

All acid-base reactions occur at rt. But what are the products/observations of phenol and sodium metal?

Na phenoxide, rapid effervescence of H2(g)

All acid-base reactions occur at rt. But what are the products/observations of phenol and NaOH?

Na phenoxide, H2O(l)

All acid-base reactions occur at rt. But what are the products/observations of CA and metal? How about with NaOH and NaHCO3/Na2CO3?

Carboxylate ion is always formed. H2(g) with metal, H2O with base and H2O + CO2 with carbonates and bicarbonates.

All acid-base reactions occur at rt. But what are the products/observations of amines and acid?

RNH3+

R&C for Iodoform test?

I2(aq) with NaOH(aq), warm

Functional groups that will give +ve result for iodoform test?

Ketones with -COCH3 and alcohols with -CH(OH)CH3

Equation code for iodoform tests

Ketone: 3433 Alcohol: 4655

R&C for Fehling's test?

Fehling’s reagent, heat

Functional groups that will give +ve result for Fehling's test?

Aliphatic aldehydes

Equation code for Fehling's test

2513

R&C for Silver Mirror test?

Tollens’ Reagent, heat

Functional groups that will give +ve result for Silver Mirror test?

All aldehydes

Equation code for Silver Mirror test?

23242

What is the unique test for phenols (R&C and observation)?

Neutral FeCl3(aq), rt (observe violet colorisation)

R&C for: Acid hydrolysis of Nitriles | Base hydrolysis of Nitriles to form CA

Dilute H2SO4, heat | Dilute NaOH, heat

R&C for: Hydrolysis of Acyl Chloride to form CA

H2O, rt

R&C for: Acid hydrolysis of Ester | Base hydrolysis of Ester to form CA and alcohol

Dilute H2SO4, heat | Dilute NaOH, heat then dilute H2SO4 at rtp

R&C for: Acid hydrolysis of Amide | Base hydrolysis of Amide to form CA and NH4+/ammonia/amine

Dilute H2SO4, heat | Dilute NaOH, heat then dilute H2SO4 at rtp